IB Chemistry HL Notes

International Baccalaureate Program
Chemistry HL
Notes
Sir Winston Churchill Secondary School
Justin Song
Table of Contents
Topic 1: Stoichiometric relationships ...................................................................................................... 1
1.1 Introduction to the particulate nature of matter and chemical change .................................... 1
1.2 The mole concept ............................................................................................................................. 3
1.3 Reacting masses and volumes ........................................................................................................ 3
Topic 2 & 12: Atomic structure ................................................................................................................ 5
2.1 The nuclear atom .............................................................................................................................. 5
2.2 Electron configuration ..................................................................................................................... 7
12.1 Electrons in atoms .......................................................................................................................... 9
Topic 3 & 13: Periodicity and the transition metals ............................................................................ 10
3.1 Periodic table .................................................................................................................................. 10
3.2 Periodic trends................................................................................................................................ 11
13.1 First-row d-block elements ......................................................................................................... 14
13.2 Coloured complexes .................................................................................................................... 17
Topic 4 & 14: Chemical bonding and structure ................................................................................... 18
4.1 Ionic bonding and structure ......................................................................................................... 18
4.2 Covalent bonding ........................................................................................................................... 18
4.3 Covalent structure.......................................................................................................................... 19
4.4 Intermolecular forces ..................................................................................................................... 21
4.5 Metallic bonding ............................................................................................................................ 22
14.1 Further aspects of covalent bonding and structure ................................................................. 23
14.2 Hybridization ............................................................................................................................... 25
Topic 5 & 15: Energetics/Thermochemistry ......................................................................................... 26
5.1 Measuring energy changes ........................................................................................................... 26
5.2 Hess’s Law ...................................................................................................................................... 27
5.3 Bond enthalpies .............................................................................................................................. 27
15.1 Energy cycles ................................................................................................................................ 28
15.2 Entropy and spontaneity............................................................................................................. 29
Topic 6 & 16: Chemical kinetics ............................................................................................................. 31
6.1 Collision theory and rates of reaction ......................................................................................... 31
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16.1 Rate expression and reaction mechanism................................................................................. 34
16.2 Activation energy ......................................................................................................................... 36
Topic 7 & 17: Equilibrium ....................................................................................................................... 37
7.1 Equilibrium ..................................................................................................................................... 37
17.1 The equilibrium law .................................................................................................................... 39
Topic 8 & 18: Acids and Bases ................................................................................................................ 40
8.1 Theories of acids and bases........................................................................................................... 40
8.2 Properties of acids and bases........................................................................................................ 40
8.3 The pH scale.................................................................................................................................... 41
8.4 Strong and weak acids and bases ................................................................................................ 41
8.5 Acid deposition .............................................................................................................................. 42
18.1 Lewis acids and bases.................................................................................................................. 42
18.2 Calculations involving acids and bases .................................................................................... 43
18.3 pH curves ...................................................................................................................................... 43
Topic 9 & 19: Redox processes ............................................................................................................... 46
9.1 Oxidation and reduction ............................................................................................................... 46
9.2 Electrochemical cells ...................................................................................................................... 48
19.1 Electrochemical cells .................................................................................................................... 48
Topic 10 & 20: Organic chemistry .......................................................................................................... 51
10.1 Fundamentals of organic chemistry .......................................................................................... 51
10.2 Functional group chemistry ....................................................................................................... 55
20.1 Types of organic reaction ............................................................................................................ 58
20.2 Synthetic routes ............................................................................................................................ 62
20.3 Stereoisomerism ........................................................................................................................... 63
Topic 11 & 21: Measurement and data processing .............................................................................. 65
11.1 Uncertainties and errors in measurement and results ............................................................ 65
11.2 Graphical techniques ................................................................................................................... 65
11.3 Spectroscopic identification of organic compounds ............................................................... 66
21.1 Spectroscopic identification of organic compounds ............................................................... 67
Option C: Energy ..................................................................................................................................... 69
C.1 Energy sources ............................................................................................................................... 69
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C.2 Fossil fuels ...................................................................................................................................... 69
C.3 Nuclear fusion and fission ........................................................................................................... 72
C.4 Solar energy ................................................................................................................................... 73
C.5 Environmental impact – global warming .................................................................................. 74
C.6 Electrochemistry, rechargeable batteries and fuel cells ........................................................... 76
C.7 Nuclear fusion and fission (AHL) ............................................................................................... 81
C.8 Photovoltaic cells and dye-sensitized solar cells (DSSC)......................................................... 82
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Topic 1: Stoichiometric relationships

1.1 Introduction to the particulate nature of matter and chemical change
Atom economy: A measure of the efficiency of a chemical reaction.

𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑢𝑠𝑒𝑓𝑢𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠
% 𝑎𝑡𝑜𝑚 𝑒𝑐𝑜𝑛𝑜𝑚𝑦 = × 100%
𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑡𝑜𝑡𝑎𝑙 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠
1
Physical properties: Qualitative and quantitative data.

Chemical properties: The ability to react with other substances.
Physical change: A reversible change of states.
Chemical change: A change of substance, causing new properties.
Law of Definite Properties: Compounds have a set ratio of elements that cannot change without
changing the compound.
Physical separation of mixtures

Hand separation:
Actual hand separation: Requires visually distinct particles.
Magnetic separation: Only works for iron, nickel, cobalt, and gallium.
Separation by mesh or sieve: Required differently sized particles.
Filtration: Separates solid particles (residue) suspended in a liquid using a filtrate.
Evaporation: Separates solids dissolved in a liquid by boiling away the solvent.
Distillation: Separates a collected liquid (distillate) from another liquid using their different
boiling points.
Solvent extraction: Separates two solutes in a solution by moving one solute to a solvent to
which it has a higher affinity using a separating funnel. Requires two immiscible solvents and
that the introduced solvent be more soluble for the solute of concern than the initial solvent.
Centrifugation: Pulls solids suspended in a liquid to the bottom of the liquid with centrifugal
force in a centrifuge.
Chromatography: Separates solid solutes in a liquid by using their solubilities for a mobile or
stationary phase. A solute’s attraction to a phase is its affinity.
Electrolysis: The application of electricity to a substance to cause a reaction.
Naming compounds
Ion charge begins with the number (3+), while oxidation number begins with the sign (+3).
Covalent compound: When naming covalent compounds, the most metallic element generally
goes first in the name.
Acid: The formula for acids begins with H, with the exception of carboxylic acids, in which case
the formula ends with -COOH.
HCl → hydrogen chloride → hydrochloric acid

HClO → hydrogen hypochlorite → hypochlorous acid
HClO2 → hydrogen chlorite → chlorous acid
HClO3 → hydrogen chlorate → chloric acid
HClO4 → hydrogen perchlorate → perchloric acid
2
Hydrate: An ionic compound that has absorbed water molecules. The formula consists of the
ionic compound, separated from the number of water molecules by a dot. The name consists of
the ionic compound’s name, followed by “[prefix]hydrate”, where the prefix is the number of
water molecules. E.g. NiSO4 ∙ 7H2O → nickel (II) sulfate heptahydrate
Peroxide: A compound containing O−O. Only bonds with species with a charge of +1.
1.2 The mole concept

Mole (NA or L): Also called Avogadro’s number, equal to 6.02 × 1023.
Isotopes: Variants of a particular chemical element that differ by neutron number.

Relative abundance: The abundance of an isotope of a chemical element in nature.
Relative atomic mass (Ar): The weighted average of the atomic masses of an element’s isotopes
and their relative abundances. Measured in μ or AMU (atomic mass units).
Relative molecular mass/Relative formula mass (Mr): The combined Ar values of the individual
atoms or ions of a molecule or formula unit.
Molar mass: The mass of a mole of an element or compound, in grams.
Percent composition: The amount of an element in a compound, by mass.
Empirical formula: The lowest whole number ratio of elements in a compound.

Molecular formula: The actual ratio between elements in a compound. Values differing by 0.05
or less are acceptable. Use single element molar masses when determining formulae.
1.3 Reacting masses and volumes

Molarity (M): Also called molar concentration, defined as the amount of substance dissolved in
a volume of solvent, in mol/L. Concentration can be represented by square brackets.
𝑣𝑜𝑙𝑢𝑚𝑒𝑖𝑛𝑖𝑡𝑖𝑎𝑙
[𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑖𝑜𝑛𝑖𝑛𝑖𝑡𝑖𝑎𝑙 ] × = [𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑖𝑜𝑛𝑓𝑖𝑛𝑎𝑙 ]
𝑣𝑜𝑙𝑢𝑚𝑒𝑓𝑖𝑛𝑎𝑙
Limiting reagent: A reagent that is completely consumed in a reaction, stopping the reaction.
Reagent in excess: A reagent that is present in amounts that exceed those required.
Theoretical yield: The expected amount of product produced in perfect conditions.

Experimental yield: The actual amount of product produced.
Percentage yield: A comparison between theoretical and experimental yield.
𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
% 𝑦𝑖𝑒𝑙𝑑 = × 100%
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
Percent purity: The purity of a sample.

𝑎𝑚𝑜𝑢𝑛𝑡 𝑝𝑢𝑟𝑒
% 𝑝𝑢𝑟𝑖𝑡𝑦 = × 100%
𝑎𝑚𝑜𝑢𝑛𝑡 𝑖𝑛𝑝𝑢𝑟𝑒
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Gasses and gas laws

Standard temperature and pressure (STP): 273.3 K (0°C) and 100.0 kPa. Results in one mole of a
gas occupying 22.7 L of space.
Avogadro’s law: Equal volumes of gas at the same temperature and pressure have the same
number of molecules, regardless of the gas.
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Boyle’s law: A gas’ pressure is inversely related to its volume. 𝑝 ∝ 𝑉
Charles’ law: A gas’ volume is directly proportional to its absolute temperature. 𝑉 ∝ 𝑇
Gay-Lussac’s law: A gas’ pressure is directly proportional to its absolute temperature. 𝑃 ∝ 𝑇

8.314𝐿∙𝑘𝑃𝑎 8.31𝐽
Ideal gas law: 𝑝𝑉 = 𝑛𝑅𝑇, where R is the universal gas constant, 𝑚𝑜𝑙∙𝐾
or 𝑚𝑜𝑙∙𝐾. The ideal gas
law assumes that:
1. The attractive forces between gas particles is negligible.
2. Gas particles have straight line motion.
3. Collisions between particles and with the walls of the container are perfectly elastic.
4. Gas particles have no volume.
Dissociation
Dissociation: The breaking apart of ionic compounds into component ions in a solvent. An
insoluble compound is one that dissociates little. A reference table is needed to specifically
determine the level of solubility of a compound. Alkali metals, ammonia (NH4+), nitrate (NO3-),
carbonate (CO32-), sulphate (SO42-), and phosphate (PO43-) are always soluble.
The equation of a reaction involving dissociated ions can be written in three ways:
1. Formula equation: The complete chemical equation.

Pb(NO3)2 (aq) + 2KI (aq) → PbI2 (s) + 2KNO3 (aq)
2. Complete/Total ionic equation: Shows dissociated ions.

Pb2+ (aq) + 2NO3- (aq) + 2K+ (aq) + 2I- (aq) → PbI2 (s) + 2NO3- (aq) + 2K+ (aq)
3. Net ionic equation: Only shows species that react or change state, no spectator ions.
Pb2+ (aq) + 2I- (aq) → PbI2 (s)
4
Topic 2 & 12: Atomic structure

2.1 The nuclear atom
History of the atom
1808: John Dalton develops the atomic model of matter and defines the atom, imagining them as
tiny spheres.
1879: William Crookes discovers the first subatomic particle by bringing a magnet near a
cathode ray and observing the ray get repulsed by the magnet.
1897: J.J. Thomson discovers the negative charge of the

cathode ray by observing it bend towards a positively
charge plate. Thomson also estimates the mass of the
cathode ray particle to be 1/2000th the mass of hydrogen.
1903: J.J. Thomson concludes that, since atoms are neutral, a positive particle must exist to
cancel out the charge of the negative particle in the cathode ray.
1909: Robert Millikan determines the mass of the

electron to be 1/1837th the mass of a proton by
suspending charged oil droplets between two charged
plates. Using the mass of an oil droplet and the
voltage required to suspend it in air, the mass of the
electron can be measured.
1909: Ernest Rutherford discovers the atomic nucleus with the gold foil experiment.
1932: James Chadwick discovers the

neutron by bombarding beryllium
with alpha particles, creating a beam
of particles that was unaffected by
magnetic and electric fields.
The atom
Atoms consist of three subatomic particles: protons (p+), neutrons (n0), and electrons (e-).
Atomic number (Z): The number of protons in the nucleus of an atom of an element.
Mass number (A): The number of nucleons (i.e. protons and neutrons) in an atom’s nucleus.
Unified atomic mass unit (amu, u): A unit of mass equal to one-twelfth the mass of a carbon-12
atom in its ground state, equivalent to 1.6605402 × 10-27 kg.
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Radioisotopes
Radioisotope: An isotope with radioactive properties.
Iodine in concentrated in the thyroid gland. Iodine-131 emits gamma rays. As such, it is used to
treat thyroid cancer and to determine whether or not a patient’s thyroid gland is functioning
normally by making the patient ingest iodine-131 and taking an image of the thyroid gland
using a gamma camera. Cobalt-60 also emits gamma rays and is used to treat cancer.
Carbon-14 is present in the atmosphere at a constant level through the bombardment of

atmospheric nitrogen-14 by neutrons from cosmic rays:
14
7𝑁 + 10𝑛 → 14
6𝐶 + 11𝐻
Organisms, using carbon as the backbone of life, ingest carbon-14 through biological
processes, maintaining a stable level of C-14 as they live. However, after death, C-14 levels
begin to decrease due to radioactive decay and a lack of replacement. As such, the ratio of
carbon-14 to carbon-12 can be used to date artifacts, using carbon-14’s half-life of 5730 years.
Mass spectrometry
Mass spectrometer: An instrument used to determine the relative atomic mass of an element. It
can also be used to show its isotopic composition.
The process of mass spectrometry has five stages:

1. Vaporization: Sample is heated and vaporized, producing gaseous atoms or molecules.
2. Ionization: The gaseous atoms are bombarded with high-energy electrons, creating
positively charge species: X (g) + e- → X+ (g) + 2e-
3. Acceleration: The positive ions are attracted to negatively charged plates and accelerated
in the electric field.
4. Deflection: The ions are deflected by a magnetic field. The degree of deflection depends
on the mass-to-charge ratio (m/z ratio) of the species, with the smallest and most charged
species being deflected the most, and neutral species not being deflected at all.
5. Detection: A detector detects the species. A mass spectrum is plotted with relative
abundance as the y-axis and m/z ratio, or the mass number (A) as the x-axis.
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2.2 Electron configuration

Electromagnetic radiation (EMR): Radiant energy that travels by waves.
Electromagnetic spectrum: The spectrum of wavelengths that comprise the types of EMR.
Wavelength (λ): The length of one complete wave, in metres or nanometres.

Frequency (ν): The number of waves that pass a point in a certain amount of time, in hertz (Hz)
or waves per second.
Amplitude: The height of a wave.
Planck’s constant (h): 6.63 × 10-34 J∙s
𝐸 = ℎ𝜈 𝑐 = 𝜆𝜈
Quantization of energy
Electrons at their lowest state of energy are
said to be in their ground state. Electrons can
absorb or release quantized amounts of
energy in the form of photons to change
energy states. The amount of energy
absorbed or released is related to the
wavelength of the photon. This energy
release shows up as bands of lights on an
emission spectrum.
Principal quantum number (n): The energy

level, with ground state being n1.
Ionization energy: The amount of energy

required to ionize an electron, n∞. When
reached, an electron either releases all of its
energy and drops to n1 or becomes a free electron.
Absorption spectrum: The absorption of particular wavelengths of light, leaving black bands in
the electromagnetic spectrum.
Rydberg equation: An equation used to calculate the wavelength of light absorbed or released
when moving between two energy levels for the hydrogen atom.
1 1 1
= 𝑅𝐻 ( 2 − 2 )
𝜆 𝑛𝑖 𝑛𝑓
RH is the Rydberg constant for hydrogen, roughly 1.097 × 107/m.

ni is the initial energy level.
nf is the final energy level.
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Orbitals and electron configurations

Orbital: A region around an atom’s nucleus in which an electron is likely to be found. Each
orbital holds 2 electrons (Pauli’s exclusion principle). The number of orbitals on each energy
level is equal to the principle quantum level, squared. There are four types of orbitals, also
called subshells:
S-orbital: Spherical shells around the

nucleus. One per energy level.
P-orbital: Figure eight shaped shells
along the x, y, and z axes. Three per
energy level.
D-orbital: Five per energy level.
F-orbital: Seven per energy level.
Inner shell orbitals: d- and f-

Valence shell orbitals: s- and p-
Aufbau principle: Electrons fill orbitals

from the lowest energy to the highest.
Hund’s rule: Orbitals of the same energy level (i.e. subshell) are filled singly first.
When writing out the electron configuration of a negative ion, simply add electrons to the
orbitals in the order dictated by the Aufbau principle and Hund’s rule:
O: 1s2 2s2 2p4 O2-: 1s2 2s2 2p6
For positive ions, remove s- and p-orbital electrons before d-orbital electrons:
V: 1s2 2s2 2p6 3s2 3p6 4s2 3d3 V2+: 1s2 2s2 2p6 3s2 3p6 3d3
V: 1s2 2s2 2p6 3s2 3p6 3d3 4s2 (IB)
Half-filled and completely filled d-orbitals are very stable. As such, copper and chromium,
along with some related elements, take their missing d-orbital electron from their s-orbital:
Cr: 1s2 2s2 2p6 3s2 3p6 4s1 3d5 Cu: 1s2 2s2 2p6 3s2 3p6 4s1 3d10
Cr: 1s2 2s2 2p6 3s2 3p6 3d5 4s1 Cu: 1s2 2s2 2p6 3s2 3p6 3d10 4s1
Core notation: A condensed form of electron configuration notation by using the nearest noble
gas core: Cu: [Ar] 4s1 3d10 Cu: [Ar] 3d10 4s1 (IB)
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12.1 Electrons in atoms

Limit of convergence: The highest wavelength of light that can be emitted by an atom’s electron
before it is ionized. An electron’s limit of convergence can be used to determine its ionization
energy with the formulae E = hν and λ = ν/c.
1 s t ionization energy trends across a period
Ionization energy and electron configuration
Ionization energy increases as

electrons are removed due to the
increase positivity of the ion and the
reduced shielding offered by
remaining electrons.
The large increases in ionization

energy are caused by the removal of
electrons from different subshells and
energy levels of different principal
quantum number (n).
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Topic 3 & 13: Periodicity and the transition metals
Topic 3 & 13: Periodicity and the

transition metals
3.1 Periodic table
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IUPAC recommended group names:

Group 1: Alkali metals Group 2: Alkaline earth metals
Group 15: Pnictogens Group 16: Chalcogens
Group 17: Halogens Group 18: Noble gases
3.2 Periodic trends

Effective nuclear charge (ENC): The net charge experienced by an electron. The effective nuclear
charge of an electron is equal to the atomic number of the atom minus the number of electrons
in shells that are closer to the nucleus than it.
Atomic radius
Bonding atomic radius (Rb): Also called covalent radius, equal to the half the distance between
the nuclei of two covalently bonded non-metallic atoms (X2).
Non-bonding atomic radius (Rnb): Also called van der Waals’ radius, equal to half the smallest
distance possible between the nuclei of two non-bonded atoms.
A bond’s length can be approximated by adding the atomic radii of its atoms.
Across a period, from left to right, atomic radius decreases. This is due to the increased effective
nuclear charge of the valence electrons being increasingly attracted to the growing number of
protons in the nucleus.
Down a group, from top to bottom, atomic radius increases. This is due to the increased number
of electron shells around the nucleus and the increased shielding effect of the additional shells.
Ionic radius
For cations, ionic radius is smaller than atomic radius. This is because cations have more
protons than electrons, causing the electrons to be more attracted to the nucleus. The more
charged the cation, the smaller the ionic radius.
For anions, ionic radius is larger than atomic radius. This is because the increased number of
electrons increases repulsion. The more charged the anion, the larger the ionic radius.
Ionization energy
Ionization energy: The minimum energy required to remove an electron from a gaseous atom in
ground state. Ionization energy roughly doubles for each electron, if they’re in the same shell.
Across a period, from left to right, ionization energy increases. This is due to increased
effective nuclear charge and decreased atomic radius causing increased attraction.
Down a group, from top to bottom, ionization energy decreases. This is due to larger
atomic radii and increase shielding causing decreased attraction.
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Reactivity
For metals, reactivity is based on how easy it is for the metal to lose electrons.
Moving across a period from left to right increases the number of protons, increasing the
attraction between valence electrons and the nucleus. This causes a decrease in reactivity.
Going down a group from top to bottom increases the amount of shielding, decreasing
the attraction between valence electrons and the nucleus. This causes reactivity to increase.
For non-metals, reactivity is based on how easy it is for the non-metal to gain electrons.
Moving across a period increases the number of protons, increasing the attraction
between electrons and the nucleus. This increase reactivity.
Going down a group increases the amount of shielding. This decreases attraction
between electrons and the nucleus, causing reactivity to decrease.
Electronegativity
Electronegativity: The relative attraction that an atom has for the shared pair of electrons in a
covalent bond. Electronegativity is measured using the Pauling scale, which ranges from 0.7
(francium) to 4.0 (fluorine).
Electronegativity trends are the same as those in ionization energy. Electronegativity

increase across a period and decreases down a group.
Trends of oxides across a period

The trends of oxides can be viewed as an increase in the ratio between the element and oxygen:
Na2O MgO Al2O3 SiO2 P4O10 SO3 Cl2O7
1:½ 1:1 1:1½ 1:2 1:2½ 1:3 1:3½
Metal oxides produce basic solutions in water, making them basic anhydrides. The dissociation
of basic anhydrides results in O2-, a strong base:
Na2O (s) → 2Na+ (aq) + O2- (aq) O2- (aq) + H2O (l) → 2OH- (aq)
Non-metal oxides produce acidic solutions in water, making them acidic anhydrides. Since non-
metal oxides are covalent or polar covalent, they don’t dissociate in water. Instead, they are
“added” to water to form an acid:
SO2 (g) + H2O (l) ↔ H2SO3 (aq) SO3 (g) + H2O (l) ↔ H2SO4 (aq)
BUT NO2 (g) + H2O (l) −/→ H2NO3 (aq) 2NO2 (g) + H2O (l) ↔ HNO3 (aq) + HNO2 (aq)
N2O5 (g) + H2O (l) ↔ 2HNO3 (aq)
Oxide reactions to memorize:

P4O10 + 6H2O → 4H3PO4 (phosphoric acid)
SO3 + H2O → H2SO4 (sulfuric acid)
Cl2O + H2O → 2HClO (hypochlorous acid)
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Al2O3 and SiO2 don’t react with water. Instead, as solid, they form covalent network lattice
structures. These compounds have high melting points. SiO2 only reacts with bases, so it is
considered an acidic anhydride:
SiO2 (s) + 2NaOH (aq) → SiO32- (aq) + H2O (l) + 2Na+ (aq)
Al2O3 is amphoteric, meaning it can react both as an acid and as a base:

acid Al2O3 (s) + 6HNO3 (aq) → 2Al(NO3)3 (aq) + 3H2O (l)
base Al2O3 (s) + 2NaOH (aq) + 3H2O (l) → 2Al(OH)4- (aq) + 2Na+ (aq)
Halogens
Halogens (group 7/17): Highly reactive non-metals with low melting points that commonly
form -1 ions and diatomic molecules.
Halogen compound Colour State at room temperature

F2 Pale yellow Gas
Cl2 Yellow/Green Gas
Br2 Red/Brown Liquid
I2 Purple/Black Solid
Since halogens are nonpolar and water is polar, only small amounts of halogens can dissolve in
water due to London dispersion attractions, creating halogen water. Halogens have one reaction
with water: X2 + H2O ↔ H+ + X- + HOX
e.g. Cl-Cl (g) + HO-H (l) ↔ H+ (aq) + Cl- (aq) + HO-Cl (aq)
Most ionic compounds containing halogens are soluble in water. Two cations have notable
reactions with aqueous halogens:
Pb2+ PbI2 (bright yellow)
Ag + AgCl (white, blackens when exposed to light, used in photographic paper)
AgBr (cream)
AgI (pale yellow)
Halogens have an order in the reactivity series for single replacement reactions. Neutral
diatomic halogens will take electrons from halogen ions below it in the reactivity series, but not
above it. A similar reaction occurs between halogens and halides:
Cl2 (g) + 2I- (aq) → 2Cl- (aq) + I2 (s) Cl2 (aq) + 2KBr (aq) → 2KCl (aq) + Br2 (aq)
I2 (s) + 2Cl- (aq) → no reaction Br2 (aq) + 2KCl (aq) → no reaction
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13.1 First-row d-block elements

Transition metal: A metallic element with an incomplete d-orbital in one or more of its
oxidation states. Zinc is not considered a transition metal because it has no incomplete d-orbital
in any oxidation state.
The elements of the d-block are classified into three types:
Type A Type B Type C

Sc, Ti, V Cr, Mn Fe, Co, Ni, Cu, Zn
Stable high oxidation states Stable high oxidation states Unstable high oxidation states
Unstable low oxidation states Stable low oxidation states Stable low oxidation states
There are two main trends across the d-block, past manganese:
1. A decreasing tendency to attain the maximum possible charge
2. An increasing tendency to attain a charge of +2
First ionization energies increase regularly through the d-block due to the five d-orbitals having
the same energy level. The ionization increase for each successive electron is also very regular.
This is what allows for the multiple oxidation states.
The range of oxidation states for

the first-row d-block metals. The
most common oxidation states
are marked in green.
+2 is the common charge of d-

block elements, since s-orbital
electrons are always lost first.
Scandium is an exception, almost
always losing its d-orbital
electron for a charge of +3.
Manganese is the middle of the first row of the d-block. To its left, elements can attain
their maximum charge by losing all their 4s and 3d orbital electrons. Charges of +5 and higher
exist only in compounds (e.g. MnO4- → Mn+7). Mn4+ is the maximum “free” charge.
Elements to the right of manganese commonly form a charge of +2, with two notable
exceptions. Fe3+ is more stable than Fe2+ because of its half-filled d-shell, while Cu+ is more stable
than Cu2+ because an s-orbital electron has already been taken by the d-orbital, leaving only one
electron to be removed.
14
Complexes of transition metals

D-block metal ions have 18 spots for electrons in their outer shell. This allows other species to
donate a pair of electrons and form a coordinate bond (formerly called dative bond).
Ligand: A species that provides electrons for a coordinate bond.
Ligands are either neutral or negatively charged species and common form four or six
attachments to a metal. Two bonds are possible, but uncommon (e.g. [Ag(NH3)2]+). Common
ligands include H2O, NH3, Cl-, and CN-.
6 ligands: H2O and NH3 (octahedral shape) 4 ligands: Cl- and CN- (tetrahedral shape)
Coordination number: The actual number of ligands in a complex ion.
Hexa-hydrated (water ligand) metal ions are commonly in aqueous solutions: [Fe(H2O)6]3+ (aq)
If a metal complex is an ion, it is written with square brackets around everything except the
charge. The charge is determined by combining the metal ion’s positive charge with the total
negative charge of the ligands.
Pauling electronegativity: An approximate method of estimating the

distribution of charge in a molecule or complex ion. For complex ions,
the metal’s charge is zero and the ligands share the overall charge.
[Fe(H2O)6]3+ Fe has a charge of 0.

1
H2O has a charge of 3 ÷ 6 = 2
Charged complex ions are soluble in water, while neutral complex ions are insoluble.
Different ligands can replace one another in their concentrations change:
[Cu(H2O)6]2+ + NH3 → [Cu(NH3)6]2+ [Cu(NH3)6]2+ + Cl- → [Cu(Cl)4]2-
Chloride ions are held tightly to complex ions. Ag+ normally precipitates with halogen ions
easily, but does not react when introduced to a complex ion containing Cl-:
[Pt(NH3)4Cl2] + Ag+ (aq) → no reaction
Classification of ligands
Monodentate ligand: A ligand capable of forming only one coordinate bond with a metal ion.
For example, NH3, H2O, CN-, and Cl-.
Polydentate ligand: Also called a chelate ligand, a ligand capable of forming two or more
coordinate bonds with a metal ion. Some polydentate ligands can form optical isomers.
15
Ethylenediamine: Also called 1,2-ethanediamine (H2NCH2CH2NH2), a bidentate ligand.

In formulae, it is abbreviated to “en”. en is an example of a ligand that can form optical isomers.
Oxalate: Also called ethanedioate, (C2O4)2-, a bidentate, dianionic ligand. Abbreviated to

“ox” in formulae names.
Ethylenediaminetetraacetate: (EDTA)4-, a polydentate ligand capable of forming up to

six coordinate bonds. EDTA can wrap itself around a transition metal centre to form an
octahedral complex. EDTA is used in the removal of heavy metals, chelation therapy for
atherosclerosis (“hardening of the arteries”), water softening, and food preservation.
The structure of transition metal complexes can be determined using X-ray crystallography if
single crystals of the complex are available. This technique can also be used to determine the
bond angles and bond distances in a structure.
Transition metals as catalysts

Transition metals speed up reactions in one of two ways:
1. Forming bonds with species or ligands, bringing them closer together and reducing the
energy needed to break bonds in the reactants.
2. Donating or accepting electrons due to their many stable charges.
Some reactions with heterogeneous metal catalysts:

- Hydrogenation of alkenes: CH2=CH2 (g) + H2 (g) → CH3CH3 (g) catalyst: Ni (s)
- Decomposition of hydrogen peroxide: 2H2O2 (aq) → 2H2O (l) + O2 (g) catalyst: MnO2 (s)
- Catalytic converters: CO (g) + NO (g) → CO2 (g) + N2 (g) catalyst: Pt (s)
- Haber process: N2 (g) + 3H2 (g) ↔ 2NH3 (g) catalyst: Fe (s)
- Contact process: 2SO2 (g) + O2 (g) ↔ 2SO3 (g) catalyst: V2O5 (s)
Magnetic properties of transition metals

Paramagnetism: A form of magnetism where a species possesses at least one unpaired electron,
making it attracted by a magnetic field.
Diamagnetism: A form of magnetism where a species only possesses paired electrons, making it
repelled by a magnetic field.
16
13.2 Coloured complexes

Degenerate orbitals: Orbitals with the same energy level.
In an isolated atom, all five d-orbitals are degenerate orbitals. In a complex ion, the d-orbitals
split into two higher energy orbitals and three lower energy orbitals.
The lower energy orbitals, composed of the dxy, dyz, and dxz orbitals, are called the t2g set.
The t2g set decreases in energy and is stabilized. The higher energy orbitals, composed of the dx2-
y2 and dz2 orbitals, are called the eg set. The eg set increases in energy and is destabilized.
Crystal field splitting energy (Δo): The difference in energy between the two split degenerate
sets of orbitals (t2g and eg). The “o” in Δo stands for “octahedral”. Δo is affected by four factors:
1. Metal ion: Δo increases down a column for the same charge

2. Charge: Δo increases as charge increases
3. Complex ion geometry: Δt for a tetrahedral complex is roughly 4/9 Δo
4. Nature of the ligand: Ordered in the spectrochemical series:
I- < Br- < Cl- < F- < [C2O4]2- ≈ H2O < NH3 < en < bpy < phen < NO2- < CN- ≈ CO
weak-field ligands − increasing Δo → strong-field ligands
The first three electrons in the d-orbital fill the t2g orbitals singularly, as per Hund’s rule.
However, the fourth electron can either fill an empty eg orbital or pair up with a previous
electron in a t2g orbital. Filling a t2g orbital requires more energy.
Pairing energy (P): The additional energy required for an electron to fill a t2g orbital.
Weak-field ligands fill eg orbitals first, thereby adopting a spin-free configuration, while
strong-field ligands fill t2g orbitals first, adopting a spin-paired configuration. For complexes
involving M3+, ligands to the right of H2O are strong-field ligands, while ligands to its left are
weak-field ligands. For complexes involving M2+, ligands to the right of NO2 in the are strong-
field ligands, while ligands to its left are weak-field ligands.
An incomplete d-orbital is required for colour. Excited electrons jump between the t2g and eg
sets, absorbing energy in the visible light spectrum. Light that isn’t absorbed (complimentary
colours) is what is seen. Different ligands have different amounts of attraction to the centre
metal, thereby requiring different amounts of energy and producing different colours.
Ligand H2O NH3 Cl-

Shape Octahedral Octahedral Tetrahedral
Co2+ [Co(H2O)6]2+ pink [Co(NH3)6]2+ straw [Co(Cl)4]2- blue
Ni2+ [Ni(H2O)6] 2+ green [Ni(NH3)6] 2+ blue [Ni(Cl)4] 2- yellow/green
Cu2+ [Cu(H2O)6] 2+ blue [Cu(NH3)4] 2+ deep blue [Cu(Cl)4] 2- yellow
square planar
17
Topic 4 & 14: Chemical bonding and structure
Topic 4 & 14: Chemical bonding and

structure
4.1 Ionic bonding and structure
Ionic bond: A bond in which an electron is lost by one atom and gained by another. Ionic bonds
have an electronegativity difference between 1.8 and 3.3, though bonds with electronegativity
differences closer to 1.8 are said to have ionic characteristics.
Under normal conditions, ionic compounds are typically solids, forming three-
dimensional crystal lattice structures. Due to the strong attraction of ionic bonds, ionic
compounds have a low volatility, meaning they are unlikely to vaporize. When melted, ionic
compounds dissociate.
NaCl (s) → Na+ (l) + Cl- (l) NOT (aq)
Individual ions are required to conduct electricity. This means that solid ionic
compounds, with their ions in fixed positions, are unable to conduct electricity, while liquid and
aqueous ionic compounds can.
Octet rule: Elements tend to lose, gain, or share electrons to acquire a noble gas core electron
configuration.
4.2 Covalent bonding

Covalent bond: A bond in which an electron is shared between two atoms. Covalent bonds have
an electronegativity difference between 0.0 and 0.2.
Polar covalent bond: A bond in which an electron is closer to the more

electronegative element, also called a polar or dipole bond, where one side is
more positive and the other is more negative. Polar covalent bonds have an
electronegativity difference between 0.2 and 1.8.
Covalent compounds consist of molecules and have lower melting and boiling points than ionic
compounds. They are also more volatile and are usually insoluble in water. Due to their lack of
ions, covalent and polar covalent compounds do not conduct electricity.
Trend in bond length: − > = > ≡ Trend in bond strength: ≡ > = > −
Bond length Bond energy Bond energy per Reactivity for

Bond
(pm) (kJ/mol) single bond breaking one bond
C−C 154 347 347 Lowest
C=C 134 619 309.5 More
C≡C 120 812 270.6 Most
18
4.3 Covalent structure

Alkali metals, alkaline metals, and group 13 (group 3) elements are stable after pairing up their
1, 2, or 3 valence electrons. Group 15 (group 5) and group 16 (group 6) elements, excluding
nitrogen and oxygen, can form 5 or 6 bonds, respectively.
Some elements can share more than one pair of electrons, forming multiple bonds. Such
elements include carbon, oxygen, and nitrogen. Metals do not do this.
Negative ions have more electrons compared to its component neutral elements. This tends to
result in a polyatomic ions that contains a non-metal with a full valence electron shell.
Meanwhile, positive ions have fewer electrons than their component neutral elements. Missing
electrons are not shown in diagrams. Instead, they are understood to be missing.
Valence shell electron pair repulsion (VSEPR) theory: Electrons repel one another to be as far
apart as possible in space.
Number of Number
electron of lone Molecular geometry Shape name Bond angle
domains pairs
2 0 Linear 180°
3 0 Trigonal planar 120°
3 1 Angular or bent <120°
4 0 Tetrahedral 109.5°
4 1 Trigonal pyramidal 107°
4 2 Angular or bent 104.5°
Trigonal 90°, 120°,

5 0
bipyramidal 180°
6 0 Octahedral 90°
19
Lone pairs of electrons occupy more space than bonding pairs, thereby decreasing the bond
angle between bonding pairs. The strength of electron pair repulsion is:
LP|LP > LP|BP > BP|BP LP = lone pair, BP = bonding pair
Electron domain geometry: The location of bonds and lone pairs around an atom.
Molecular geometry: The shape of a molecule.
Resonance structures: The various Lewis structures for an identical arrangement of atoms with
different arrangements of the electrons.
Molecular polarity: Whether a molecule is polar or non-polar. Molecules must have polar
covalent bonds to be polar, but not all molecules with polar covalent bonds are polar. This is
because the polarity of two equal bonds opposite to each other cancel out. Lone pairs usually
make a molecule polar.
Allotropes
Allotropes: Different forms of an element in the same physical state.
Covalent lattice network: A structure where atoms are held together by covalent bonds in a
giant three-dimensional lattice structure.
Allotropes of carbon
Diamond: An allotrope of carbon where each carbon atom is three-dimensionally single bonded
in a tetrahedral (109.5°) covalent network structure. Diamond has a very high melting point and
does not conduct electricity.
Graphite: An allotrope of carbon in which carbon rings are joined together in a two-dimensional
plane, with delocalized electrons above and below the sheet. Each carbon atom is bonded to
three other atoms, forming a trigonal planar geometry (120°). The sheets of carbon lie on each
other, held together by London dispersion forces. Graphite conducts electricity through its
delocalized π electrons, but can only conduct electricity within one sheet.
Graphene: A single sheet of graphite, considered the first two-dimensional crystal to be

discovered. Graphene is very strong and conducts heat and electricity 300 times better than
copper. A 1mm thick sheet of graphite contains around 3 million sheets of graphene.
Carbon nanotube: A rolled up tube of graphene. Carbon nanotubes are around 10-9 metres in
diameter and are 100 times stronger than steel.
20
Fullerene: A carbon nanotube that is folded up into a sphere. Fullerenes are composed of
systems of 5- or 6-carbon rings, where each carbon is bonded to three others. Fullerenes can’t
conduct electricity, but they can accepts electrons and become negatively charged. The most
well-known fullerene is C60, also called buckminsterfullerene, although other fullerenes exist,
such as C90 and C120.
Fullerenes are molecules, not covalent network structures. Their non-polarity results in
relatively low melting points and allows them to dissolve in non-polar solvents. Fullerenes can
undergo addition reactions across their double bonds, unlike benzene, and are compressible
due to their spherical shape. They can also hold a species inside their spherical structure,
creating an inclusion complex.
Silicon dioxide (SiO2): Also called silica, it is found in its amorphous (no ordered structure) form
as sand. Its most common crystalline form is quartz, where it consists of a three-dimensional
covalent network lattice. Due to its strong covalent bonds, silicon dioxide has a high melting
and boiling point.
Coordinate covalent bond: A covalent bond in which both electrons are donated
by one atom.
In its solid state, aluminum chloride is ionic, forming AlCl3 in a crystal

lattice. AlCl3 normally sublimes, but will melt if heated under pressure, at which
point it forms the dimer Al2Cl6, which contains coordinate covalent bonds.
4.4 Intermolecular forces

Intermolecular force: Interactions between molecules.
Intramolecular force: Interactions within a molecule. Covalent, polar covalent, and ionic bonds
are all considered intramolecular bonds, and sometimes intramolecular attractions.
Hydrogen bonding: The strongest type of intermolecular attraction, roughly 1/10th the strength
of a covalent or ionic bond. Hydrogen bonding occurs when hydrogen is bonded to oxygen,
nitrogen, or fluorine. Hydrogen bonding is represented by three dots:
X−H ∙ ∙ ∙ Y−Z
Hydrogen bonding is not the bond itself, but is a result of hydrogen’s polar covalent
bonding. Without any electron shells to shield its nucleus, when a very electronegative element
(oxygen, nitrogen, fluorine) pulls in the hydrogen’s electron, its nucleus’s attraction is exposed.
Intramolecular hydrogen bonding also exists, when parts of a large molecule are
attracted to each other through hydrogen bonding.
Dipole-dipole attraction: Similar to hydrogen bonding, but weaker due to electrons screening
their atom’s nucleus. Dipole-dipole attraction only occurs between polar molecules.
21
London dispersion forces (van der Waals attraction): The

attractive forces between molecules due to momentary
attraction between the electrons and nuclei of two atoms.
Momentary dipoles in one species can induce dipoles in

others. The chances of an attractive force between two
molecules are greater than a repulsive force.
Two factors affect the strength of London dispersion forces:
1. Number of electrons: More protons and electrons results in more attraction, increasing
the strength of London dispersion forces. Since the number of electrons a species has is
related to its molar mass, a greater molar mass results in greater attraction.
2. Surface area: A larger area for possible attraction increases the strength of London
dispersion forces.
Two species must have some amount of intermolecular attraction to stay together in a mixture
and be soluble. For two polar species, this is either hydrogen bonding or dipole-dipole
attraction. For two non-polar species, this is London dispersion forces. However, for a polar and
non-polar species, there is no attractive force, meaning they are insoluble and immiscible.
Relative strength of bonds and attractions:

Covalent/Polar covalent/Ionic > Hydrogen bonding >> Dipole-dipole > London dispersion
A stronger attractive force means more energy is required to break the intermolecular
attractions. This raises the melting and boiling point of the species.
4.5 Metallic bonding

Metallic bond: The electrostatic attraction between a lattice of positive ions and delocalized
electrons, caused by the relatively low electronegativity of metals. The delocalized electrons
give metals their heat and electricity conductivity and their lustre. Malleability and ductility are
caused by the fact that the metal atoms aren’t “directly” bonded to each other, allowing them to
slide past each other while still remaining attracted together.
Alloy: A mixture of metals or a mixture of a metal and other elements. Alloys have greater
resistance to corrosion and enhanced magnetic properties compared to pure metals. They are
also stronger than pure metals due to the differently sized particles resisting applied forces.
Due to the strength of metallic bonds, metals have high melting and boiling points. The melting
and boiling point of metals increases across a period due to a greater attraction caused by more
valence electrons. Melting and boiling point decrease down a family due to more electron
shielding and larger distances between nuclei and electrons.
22
14.1 Further aspects of covalent bonding and structure

Formal charge
Formal charge (FC) can be used to predict the most likely bonding structure of a species when
more than one is possible.
1
𝐹𝐶 = 𝑎𝑐𝑡𝑢𝑎𝑙 # 𝑜𝑓 𝑣𝑎𝑙𝑒𝑛𝑐𝑒 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠 − (# 𝑜𝑓 𝑏𝑜𝑛𝑑𝑖𝑛𝑔 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠) − # 𝑜𝑓 𝑛𝑜𝑛𝑏𝑖𝑛𝑑𝑖𝑛𝑔 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠
2
∆𝐹𝐶 = 𝐹𝐶𝑚𝑎𝑥 − 𝐹𝐶𝑚𝑖𝑛
The bonding structure with the ΔFC value closest to 0 is considered to be the actual
structure. If several ΔFC values are the same, the most electronegative element should have the
most negative FC value.
Example: Cyanate (OCN-)
O≡C−N- O=C=N- O−C≡N-

FC(O) = 6 – ½(6) – 2 = 1 FC(O) = 6 – ½(4) – 4 = 0 FC(O) = 6 – ½(2) – 6 = -1
FC(C) = 4 – ½(8) – 0 = 0 FC(C) = 4 – ½(8) – 0 = 0 FC(C) = 4 – ½(8) – 0 = 0
FC(N) = 5 – ½(2) – 6 = -2 FC(N) = 5 – ½(4) – 4 = -1 FC(N) = 5 – ½(6) – 2 = 0
ΔFC = 1 – (-2) = 3 ΔFC = 0 – (-1) = 1 ΔFC = 0 – (-1) = 1
Since oxygen is more electronegative than nitrogen, O−C≡N- is the most probable structure.
Delocalization and resonance

Compounds with double or triple bonds may have resonance structures, but, in reality, there
exists only one molecule. Double and triple bonds have pi bonds, which are delocalized to
create the resonance hybrid structure, the true structure of the molecule.
As an example, take benzene. The three pi bond

electron pairs in benzene are spread out over the entire ring,
with one electron from each pair above and the other below.
Evidence to support the delocalized electrons in benzene:

1. All benzene bond lengths are the same, making it
planar, something it wouldn’t be if the double bonds
weren’t delocalized.
2. The predicted amount of energy released by burning
benzene using single and double bonds is different
from experimental observation due to the stability
associated with the delocalized electron ring.
3. Reactions that occur with double bonds do not occur
with benzene.
23
The resonance hybrid structure can be shown in two ways:

1. A dotted line along the delocalized pi bond
2. Shaded areas above and below the area of delocalization
Since the delocalized electron is spread across multiple bonds, its charge is divided up over the
total number of bonds across which the electron is distributed. In the example above, the charge
of the electron is distributed across two bonds, making its charge ½ for each bond.
Bond order: The number of chemical bonds between a pair of atoms, equal to the sum of the one
sigma bond and the fractional pi bonds. In the above example, the bond order for the C–O
bonds is 1.5.
In organic chemistry, long hydrocarbon chains can alternate single and double bonds, forming
conjugated chains. Electrons are delocalized along the entire conjugated portion.
Molecular geometry based on five and six electron domains

Number of Number of Molecular
Shape name Bond angle
electron domains lone pairs geometry
Trigonal
5 0 90°, 120°
bipyramidal
5 1 See-saw <90°, <120°
5 2 T-shaped <90°
5 3 Linear 180°
6 0 Octahedral 90°
6 1 Square pyramidal <90°
6 2 Square planar 90°
24
Catalysis of ozone depletion

Due to the delocalization of ozone’s double bond, its bond order is 1.5, as opposed to oxygen’s
bond order of 2. This allows for ozone’s bonds to be broken by UV radiation instead of a shorter
wavelength of light with a higher amount of energy. As such, the ozone in the atmosphere
protects life on Earth from UV radiation.
O3 (g) −UV→ O2 (g) + O∙ (g) O2 (g) + O∙ (g) → O3 (g) + heat
However, the introduction of chlorofluorocarbons into the atmosphere during the mid-20th
century has increased the rate of ozone depletion, allowing more UV radiation to reach the
Earth’s surface and increasing the risk of skin cancers and cataracts.
CF2Cl2 −UV→ CF2Cl∙ + Cl∙ Cl∙ + O3 → ClO∙ + O2 ClO∙ + O3 → Cl∙ + 2O2
14.2 Hybridization
Hybridization: The mixing of atomic orbitals to form hybrid atomic orbitals.
Normally, p-orbitals have a higher energy level than s-

orbitals. However, in compounds such as methane, the
four bonds of the carbon atom force an s-orbital
electron into the empty p-shell and move all four shells
to the same energy level, creating the sp3 orbital.
A single bond is formed by overlapping two hybridized orbitals, creating a sigma (σ) bond. For
double or triple bonds, one or two of the p-orbitals don’t hybridize, creating sp2 and sp
hybridization. When unhybridized orbitals overlap, they form pi (π) bonds.
Hybridized orbitals retain the characters of their constituent orbitals. The ratio of character
depends on the type of hybridized orbital created:
sp3: 25% s, 75% p sp2: 33% s, 67% p sp: 50% s, 50% p
25
Topic 5 & 15: Energetics/Thermochemistry

5.1 Measuring energy changes
Enthalpy (H): The heat content of a species. Bonds have potential energy, which it associated
with heat energy when they are formed or broken. Enthalpy cannot be measured directly, but
change in enthalpy (ΔH) can. Energy must be added to break bonds and energy is released
when bonds form. ΔH is the overall difference between the two processes.
ΔH is not related to the rate of a reaction. It is usually given in kJ/mol and applies to the
reaction as a whole. Changing the coefficients of reactants in a formula also changes ΔH.
2C2H6 (g) + 5O2 (g) → 2CO2 (g) + 6H2O (l) ΔH = 200 kJ/mol ←despite no 1 mol reactant
Endothermic reaction: A reaction in which the products absorb additional energy from their
surroundings, giving the products a higher potential energy value than the reactants.
Endothermic reactions have a positive ΔH value.
Exothermic reaction: A reaction in which the reactants release energy into their surroundings,
giving the reactants a higher potential energy value than the products. Exothermic reactions
have a negative ΔH value.
For examining energy changes in reactions, the Universe is divided into two parts:
- System: Reactants, products, ΔH, solvent
- Surroundings: Everything else
Standard reaction conditions: 25°C (298K), 100.0 kPa, 1.0M solutions

ΔH at standard conditions: θ or ΔHθ
Calculating enthalpy changes

Changes in energy, not enthalpy, can be calculated using the equation
𝑄 = 𝑚𝑐∆𝑇
Where Q is the change in energy of a system, in joules

m is the mass of the substance, in grams
ΔT is the change in temperature of the system, in °C or K
𝐽
c is the specific heat capacity of the substance, in 𝑔℃
The change in enthalpy can be determined by dividing the change in energy by the number of
moles of reagents reacted. Always check for limiting reagents.
Bomb calorimeter: An insulated chamber for heat energy experiments. Since some heat is
always lost, the calculated ΔH value is lower than the actual value. To compensate for this, the
change in temperature of the calorimeter itself should be included in the energy calculation.
26
When determining the change in temperature

from a temperature-time graph, extrapolate the
slope of the temperature after the reaction has
occurred back to the time when the reaction took
place. Use this extrapolated temperature as the
change in temperature.
5.2 Hess’s Law

Hess’s Law: Regardless of the route by which a chemical reaction proceeds, the enthalpy change
will always be the same, provided the initial and final states of the system are the same.
Different reaction routes can be shown using an enthalpy cycle diagram.
The coefficients of the actual reaction must be used for an enthalpy cycle diagram. Fractional
coefficients and reversing equations are allowed. According to Hess’s Law,
∆𝐻1 = ∆𝐻2 + ∆𝐻3 = ∆𝐻4 + ∆𝐻5 + ∆𝐻6
5.3 Bond enthalpies

Bond enthalpy (BE): The energy required to break one mole of a certain type of bond in gaseous
form under standard conditions. Also called bond dissociation energy.
Tables of bond enthalpies can be used to calculated the ΔH value of a reaction.

However, there is an uncertainty associated with these tables. A 10% error is associated with
bond enthalpy values for liquid and solid states. Furthermore, because the values for some
bonds (e.g. C-H) are averaged over many different compounds, bond enthalpies are only an
approximation.
∆𝐻𝑟𝑒𝑎𝑐𝑡𝑖𝑜𝑛 = ∑ 𝐵𝐸 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠 − ∑ 𝐵𝐸 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠
27
Standard enthalpy of formation (ΔHfθ): The energy required to make one mole of a compound
from its elements at standard conditions.
Elements in their standard states have a ΔHfθ value of zero. Most compounds have a
negative ΔHfθ value, since they give off energy. However, some compounds have a positive
ΔHfθ value because more energy is used to break the bonds in the elements than is given off
when the compound is formed.
∆𝐻 = ∑ ∆𝐻𝑓𝜃 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠 − ∑ ∆𝐻𝑓𝜃 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠
Enthalpy of combustion (ΔHcθ): The energy released when one mole of a compound is
completely combusted with excess oxygen gas at standard conditions. All combustion reactions
are exothermic, meaning ΔHcθ is always negative.
The ΔHcθ value for elements is equal to the ΔHfθ value of the product compound, since
the product compound is formed from the two reactant elements.
Two common formation/combustion reactions:

ΔHfθ (CO2) = -395 kJ/mol
C (s) + O2 (g) → CO2 (g)
ΔHcθ (C) = -395 kJ/mol
ΔHfθ (H2O) = -287 kJ/mol
H2 (g) + ½O2 (g) → H2O (g)
ΔHcθ (H2) = -287 kJ/mol
15.1 Energy cycles

Lattice energy and the Born-Haber cycle
Lattice energy (ΔHlat): The energy required to change a solid ionic compound into separate
positive and negative gaseous ions.
Direct measurement of lattice energy is not possible. Instead, it can be deduced by

looking at two different pathways to get from the elements in standard state to their separate
gaseous ions and using Hess’s law. The two different pathways form the Born-Haber cycle.
Enthalpy of atomization (ΔHat): The energy

needed to change one mole of an elemental
substance into gaseous atoms.
Electron affinity (ΔHEA): The energy

associated with gaining an electron. Usually a
negative value.
Ionization energy (ΔHIE): The energy needed

to remove an electron from an atom.
𝜃
∆𝐻𝑙𝑎𝑡 = ∑ ∆𝐻𝑎𝑡 𝜃
+ ∆𝐻𝐸𝐴 𝜃
+ ∆𝐻𝐼𝐸 − ∆𝐻𝑓𝜃
28
Lattice energy is affected by the ionic charge and the ionic radii. A greater charge implies a
stronger attraction between the ions, thereby increasing lattice energy. A larger ionic radius
increases the distance between the ions, thereby lowering lattice energy.
Enthalpy change of solution

Enthalpy change of solution (ΔHsol): The energy associated with dissolving one mole of a
substance in an excess amount of a pure solvent. ΔHsol can be either positive or negative. A
negative enthalpy change of solution means that the compound will dissolve.
Enthalpy change of hydration (ΔHhyd): The energy associated with dissolving one mole of
gaseous ions in water to form a dilute solution. ΔHhyd is always negative.
Both a smaller number of shells and a greater charge make it easier for an ion to form a
hydration shell, thereby lowering the enthalpy change of solution. Increasing the temperature
of a system can help less soluble compounds dissolve by adding the additional energy required.
15.2 Entropy and spontaneity

Entropy
𝐽
Entropy (S): A measure of the disorder of a substance, expressed in 𝐾∙𝑚𝑜𝑙. A substance’s gaseous
state has a lot more entropy than its liquid or solid state.
∆𝑆 = ∑ ∆𝑆 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠 − ∑ ∆𝑆 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠
If the ΔS value of a reaction is positive, its products are more disordered. If the ΔS value is
negative, its reactants are more disordered.
Spontaneity and Gibbs free energy

The two driving factors of a reaction are enthalpy and entropy. Reactions have a natural
tendency to lose energy (i.e. negative ΔH value) and become more disordered (i.e. positive ΔS
value). There are three permutations of enthalpy and entropy in a reaction:
1. Both factors favour the products. Such a reaction is spontaneous and will occur.
2. Both factors favour the reactants. Such a reaction is nonspontaneous and will not occur.
3. The factors favour opposite sides. Such a reaction is an equilibrium and will result in a
balance of products and reactants.
29
Gibbs free energy (ΔGθ): The amount of energy that can be obtained from a reaction, provided a
given entropy, enthalpy, and temperature.
∆𝐺 𝜃 = ∆𝐻 − 𝑇∆𝑆
If ΔGθ is negative, the reaction is spontaneous. If it is positive, the reaction is nonspontaneous.
For the first two possibilities mentioned above, the sign of ΔGθ does not change,
meaning it is either always spontaneous or always non-spontaneous. However, for the third
possibility (i.e. equilibriums), a change in temperature can cause a switch between being
spontaneous and nonspontaneous.
How temperature affects an equilibrium depends on whether it is endothermic or

exothermic. In endothermic reactions, an increase in temperature favours the products, making
the reaction spontaneous at high temperatures. In exothermic reactions, the reverse is true.
Gibbs free energy change of formation (ΔGfθ): The amount of energy that can obtained from the
formation of a compound from its component elements under standard conditions.
∆𝐺 𝜃 = ∑ ∆𝐺𝑓𝜃 𝑝𝑟𝑜𝑑𝑢𝑐𝑡𝑠 − ∑ ∆𝐺𝑓𝜃 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠
30
Topic 6 & 16: Chemical kinetics

6.1 Collision theory and rates of reaction
Reaction rate
Rate of reaction: The rate at which a reaction progresses. To measure reaction rate, a property
∆[ ]
must change over time in the reaction. The standard unit of rate is ∆𝑇𝑖𝑚𝑒, or mol∙dm-3∙s-1.
∆𝑃𝑟𝑜𝑝𝑒𝑟𝑡𝑦
𝑅𝑎𝑡𝑒 =
∆𝑇𝑖𝑚𝑒
Measuring the rate of a chemical reaction
Possible properties to measure reaction rate:
- Mass: Loss in reactant mass or gain in product mass. The substance measured must have a
high enough molar mass to show a significant change in mass. For instance, measuring the
production of hydrogen would not be suitable.
- Volume or pressure: Only applies to gases. If a gas that is soluble in water is being collected
as it bubbles through water, its yield will be decreased to an extent.
- Concentration: Decrease in reactant concentration or increase in product concentration.
- Colour: Appearance of disappearance of colour.
- pH or acidity
- Temperature: Not ideal, as temperature itself changes reaction rate.
- Conductivity: Requires a reaction where one side has ions in solution and the other side
doesn’t. As such, conductivity changes as the reaction progresses.
- Light absorption: The amount of time for a precipitate to block out a mark on the bottom of
a beaker. A more precise method be to use a spectrophotometer or colorimeter.
- Clock reaction: Involves two separate reactions that are linked together, where one reaction
either produces or uses up a coloured species. When the coloured species appears or
disappears, the reaction time is noted.
E.g. H2O2 + 2I- + 2H+ → I2 + H2O
2S2O32- + I2 → S4O62- + 2I-
I2 is purple, while I- is colourless. Once S2O32- runs out, the solution turns purple.
- Titration: Removing samples out of the reaction mixture and titrating them to determine
how much of a reactant remains. Titration carries a level of uncertainty due to the reaction
continuing after a sample is removed. This uncertainty can be reduced by stopping
(quenching) the reaction . Quenching can be done by adding a substance that reacts out a
reagent or reducing the temperature.
E.g. H2O2 (aq) + 2H+ (aq) + 2I- (aq) → 2H2O (l) + I2 (aq)
To titrate H2O2, neutralize the H+ by adding excess OH-, creating H2O.
31
Reaction rates change during a reaction. As such, using the initial portion of the reaction is the
best method of determining reaction rate. Some reactions, such as the iodine clock reaction,
must be completed. In these cases, rate is inversely proportional to time.
When graphing the change in a property over time, assume that the reaction starts just with
reactants. Focus only on the products when they are being used to measure a property. A
reaction’s rate will slow as it progresses due to there being fewer reactants to react.
Reaction rate can be calculated from a graph two ways – instantaneous rate and average rate.
Instantaneous rate can be found using derivatives, while average rate is calculated by dividing
the change in concentration by the time elapsed. Reaction rates are always positive.
Reactants react at the same time that products are form. As such, they are directly linked to each
other. Using this, the rate of any species in a reaction can be calculated through stoichiometry,
so long as the rate of one species is known.
Factors that affect reaction rates

- Nature of reactants: If all factors are the same, save for one reactant, or if observations are
counter-intuitive (e.g. higher temperature → slower reaction), it is due to the nature of
reactants.
- Breaking bonds vs electron transfer: Electron transfer needs less energy, making it faster.
- Aqueous ions in solution: Aqueous ions can move freely in solution, meaning aqueous ions
will react faster than other states.
- Concentration: Concentration is proportional to reaction rate. In collision theory, there are
more particles, meaning more successful collisions and more products. Changing the mass
of a solid isn’t changing its concentration.
- Temperature: Temperature increases reaction rate. In collision theory, additional heat
energy makes the particles move faster. More energetic collisions are more successful and
faster particles have more collision per unit time.
- Geometry of collision: Molecules must be in the correct orientation for a successful collision.
Optimal geometry minimizes the amount of energy required.
- Pressure: Applies to gases only. Pressure is inversely proportional to volume. Increasing
pressure decreases volume, which effectively increase concentration.
- Surface area: Only applies to heterogeneous phases, creating a “surface” between the two
phases. Surface area is proportional to reaction rate. Heterogeneous phases are: solid-liquid,
solid-gas, liquid-gas, and liquid-liquid (immiscible). All other phases are homogeneous.
 Catalyst: Something that increases reaction rate without being used up. Anything that
decreases reaction rate is an inhibitor, either by blocking collisions or binding to a reactant,
thereby requiring more energy to collide.
32
Catalysts
Homogeneous catalyst: A catalyst in the same state as the reactants. Homogeneous catalysts
tend to speed up reactions through the transfer of electrons:
H2O2 (aq) + 2H+ (aq) + 2Fe2+ (aq) → 2H2O (l) + 2Fe3+ (aq)
2I- (aq) + 2Fe3+ (aq) → I2 (s) + 2Fe2+ (aq)
∴ H2O2 (aq) + 2H+ (aq) + 2I- (aq) → 2H2O (l) + I2 (s) catalyst: Fe2+ (aq)
Heterogeneous catalyst: A catalyst in a different state to the reactants.
Temperature and the Distribution of Kinetic Energy in a Sample

Maxwell-Boltzmann distribution curve:
The distribution of the kinetic energies of a gas
sample’s particles.
By increasing the temperature of a reaction,

the curve shifts towards the right, placing
more particles above the threshold energy for
a reaction. In general, a “slow” reaction’s rate
roughly doubles for every 10°C increase in
temperature.
Activation energy: The amount of extra energy required to start a reaction.
Eact(f): Activation energy for forward reaction.
Eact(r): Activation energy for reverse reaction.
Activated complex: The intermediate molecule of a

reaction formed when particles collide. Activated
complexes are actual molecules. However, they are
very short-lived and not stable. They also have a high
potential energy compared to the reactants and
products of their reaction.
Note that peak activation energy isn’t the activated complex itself. Rather, the activated
complex has the energy associated with the bump in energy. The extra energy used to form the
activated complex comes from the kinetic energy of the colliding particles. The enthalpy value
of a reaction (ΔH) doesn’t really affect reaction rate. Instead, activation energy does.
33
16.1 Rate expression and reaction mechanism

Rate equations
For any reaction aA + bB → cC + dD, the reaction rate can be expressed using the equation:
𝑟𝑎𝑡𝑒 = 𝑘[𝐴]𝑥 [𝐵]𝑦
Where k is the rate constant. Note that the exponents x and y have no relation to the balanced
reaction coefficients a and b. The only method of determining a rate equation is experimentally.
The values of x and y are the orders of [A] and [B], respectively. The overall order of a reaction
is equal to the sum of the orders of the reactants.
Determining the rate equation

To determine the rate equation of a reaction, the order of its reactants must be known. This is
determined by varying the concentration of one reactant, while keeping the concentrations of
the others the same. The order of a reactant is calculated based on the resulting change in
reaction rate in relation to the change in concentration.
Change in concentration Change in rate Order of reaction

×n 0 0
×n ×n 1
×n ×n2 2
×n ×n3 3
0 order reactants aren’t included in rate equations. Once all orders of reaction are known, a
known reaction rate and concentration for each reactant is substituted into the rate equation to
determine the rate constant.
The ideal conditions for determining the order of a reagent would be to make it the limiting
reagent, with low concentration, and have the other reagents in excess.
The order of reaction of a reactant can also be determined through various graphs.
Rate vs concentration graph
0th order: No change in rate with change in reactant

concentration.
1st order: Linear change in rate with linear change in

reactant concentration.
2nd order: Exponential change in rate with linear

change in reactant concentration.
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Concentration vs time graph
0th order: Linear decrease in reactant concentration

until depleted.
1st order: Exponential decrease in reactant

concentration. The reactant’s half-life is constant.
ln 2
𝑡1 =
2 𝑘
2nd order: Similar to 1st order reactants, except the

half-life of the reactant doubles with each halving.
Reaction mechanisms
Reaction mechanism: The series of elementary steps by which an overall reaction occurs.
Since it is very unlikely for more than two particles to collide at the same time, with the correct
collision geometry, and with sufficient kinetic energy, reactions involving more than two
particles have mechanisms with more than one elementary process.
Each elementary process has its own activated complex and activation energy. The elementary
step with the highest activation energy limits the reaction’s rate. As such, it is the rate
determining step of the reaction. An elementary process’ activation energy is measured from
where the process starts, not the initial reactant potential energy level. The products of
elementary processes are located in the valleys between energy peaks.
Catalysts cause a reaction to go through a set of

elementary steps with lower activation energies.
Since the activation energy is lower, more
particles have a sufficient amount of energy to
react, thereby speeding up the reaction.
Reaction intermediate: A species produced in

one mechanism step that is used up in one of
the following steps. A reaction intermediate is
an actual molecule that can exist for an extended
period of time, is stable, and can be isolated.
Reaction intermediates have a lower potential
energy than their associated activated complex.
Reaction mechanism example: 4HBr (g) + O2 (g) → 2H2O (l) + 2Br2 (g)
1. HBr + O2 → [HBrO2] → HOOBr Slow, ∴ rate determining step
2. HOOBr + HBr → [HBrHOOBr] → HOBr + HOBr Fast
3. HOBr + HBr → [HOBrHBr] → H2O + Br2 Fast, done twice
35
1. HBr + O2 → HOOBr
2. HOOBr + HBr → 2HOBr
3. 2HOBr + 2HBr → 2H2O + 2Br2
4HBr + O2 → 2H2O + 2Br
Before determining a rate equation for a reaction, a reaction mechanism must be proposed, then
experimentally verified. This is because rate equations are based on the species in the rate
determining step of the mechanism. If the elementary step before the rate determining step is an
equilibrium, its reactants are also included in the rate equation. Reaction intermediates aren’t
part of rate equations, though catalysts can be.
Molecularity: The number of particles involved in the rate determining step of a reaction.
One molecule → unimolecular, two molecules → bimolecular, three molecules → termolecular.
16.2 Activation energy

Arrhenius equation: A formula for the rate constant of a reaction, k, given a certain temperature.
−𝐸𝑎𝑐𝑡
𝑘 = 𝐴𝑒 𝑅𝑇
Where A is the Arrhenius constant, a value related to the rate and geometry of collisions
Eact is the activation energy of the reaction
R is the universal gas constant (8.31 J∙K-1∙mol-1)
T is the temperature (in K)
From the equation, it can be seen that temperature has an exponential effect on rate of a
reaction. The Arrhenius equation can be rearranged by applying the ln function to both sides:
−𝐸𝑎𝑐𝑡
ln 𝑘 = ln 𝐴𝑒 𝑅𝑇
𝐸𝑎𝑐𝑡
ln 𝑘 = ln 𝐴 −
𝑅𝑇
−𝐸𝑎𝑐𝑡 1
ln 𝑘 = ( ) ( ) + ln 𝐴
𝑅 𝑇
−𝐸𝑎𝑐𝑡
Resulting in an expression whose form is that of a straight line, 𝑦 = 𝑚𝑥 + 𝑏, with slope 𝑅
and
y-intercept ln 𝐴. As such, measurements of the rate of a reaction at different temperatures can be
1
plotted on a 𝑇 vs ln 𝑘 graph.
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Topic 7 & 17: Equilibrium

7.1 Equilibrium
Equilibrium: A reaction where both forward and reverse reactions occur simultaneously. An
equilibrium requires a closed system. Since energy is somewhat difficult to contain, maintaining
a constant temperature is sufficient for equilibriums. So long as the total number of particles
remains constant, the equilibrium position will always be reached, regardless of the initial ratio
of reactant to product.
Since equilibriums are reversible, they may be written in either direction. However, the reaction
must be discussed in the form it was given in a question.
Dynamic equilibrium: When the rates of the forward and reverse reactions are equal. On the
macroscopic level, properties are constant. On the microscopic level, molecules are still being
converted between the two phases.
Macroscopic properties that can be used to determine if an equilibrium has been reached:
 Colour  pH (acidity)  Conductivity
 Volume  Concentration  Temperature (not ideal)
Once the macroscopic property stops changing, an equilibrium may have been reached. Mass
doesn’t really work because it may not change or may be inaccessible in a closed system.
Factors that affect equilibrium

Pressure/Volume: Only affects reactions with gases. Increasing pressure/decreasing volume
essentially increases the concentration of a gas, increasing the number of collisions.
If only one side of the equilibrium contains a gas, an increase in pressure/decrease in

volume will cause the equilibrium to shift away from the side with the gas.
If both sides of the equilibrium contain a gas, the resulting change depends on the
coefficients of the balanced reaction. If the coefficients are the same, the equilibrium doesn’t
shift. If they aren’t the same, an increase in pressure/decrease in volume causes the equilibrium
to shift towards the side with fewer gas particles.
Temperature: Always causes a shift in the equilibrium position. In terms of energy, an increase
in temperature provides energy to the side of the reaction with the ΔH value. This causes the
equilibrium to shift away from that side. Conversely, a decrease in temperature shifts the
equilibrium towards the side with the ΔH value by reducing the amount of energy.
Increase in temperature Decrease in temperature

Endothermic reaction Towards products Towards reactants
Exothermic reaction Towards reactants Towards products
37
Enthalpy (ΔH) and entropy (S, ΔS): Reactions naturally lose energy to their surroundings. This
causes reactions to move towards the side with the enthalpy term in an attempt to move
towards minimum enthalpy.
Reactions naturally become more disordered. This causes reactions to move towards the
side with the most entropy in an attempt to move towards maximum entropy. Recall the order
of states is, from least to most disordered: Solid → Pure liquids → Aqueous ions → Gases.
Concentration: In terms of collision theory, an increase in a species’ concentration results in

more collisions for that species compared to other species, causing the equilibrium to shift away
from the species’ side. Conversely, reducing a species’ concentration causes the equilibrium to
shift towards its side.
Catalysts: Since catalysts reduce the activation energy of the forwards and backwards reaction
by the same amount, the equilibrium doesn’t shift. If a reaction isn’t at equilibrium, a catalyst
will help it reach equilibrium faster.
Graphing changes to pressure, temperature, and concentration

When something is done to change a system at equilibrium, two things occur:
1. The equilibrium undergoes stress, caused by the change
2. The equilibrium tries to adjust for the stress, usually shifting in one direction
Change in pressure/volume: Only affects gases in a reaction. All gases in a reaction are affected
at the same time. The equilibrium doesn’t shift if the number of gas particles on each side of the
equation is the same.
Change in concentration: The entire equilibrium shifts to compensate for a change in

concentration in one species. Note how, in the concentration change graph, the affected species
doesn’t quite return to its original concentration in the new equilibrium.
Change in temperature: The change in temperature graph is the only graph of the three not to
directly show the stress applied on the equilibrium.
Catalysts do not change the concentrations of an equilibrium.
38
Le Chatelier’s principle
When a stress is imposed on a system at equilibrium, the system will shift to counteract and
reduce the stress, if possible.
Change in concentration: If the concentration of one species is increases, the equilibrium shifts
towards the opposite side of the reaction to reduce the increased concentration.
Pressure: An increase in pressure causes the equilibrium to shift towards the side with fewer
particles to reduce the increase in pressure.
Temperature: An increase in temperature causes the side of the reaction with the enthalpy term
to absorb the added heat energy, shifting the reaction to the side without the enthalpy term.
The Haber Process

The process of producing ammonia from the equilibrium
3H2 (g) + N2 (g) ↔ 2NH3 (g) + 92.4kJ
High pressure and low temperature are ideal for the equilibrium to favour the ammonia side.
However, high pressure containers are expensive and hard to maintain, and low temperatures
result in low reaction rates. As such, moderate temperatures and pressures are used.
17.1 The equilibrium law

Equilibrium constant (Keq, Kc): The ratio of the concentration of an equilibrium’s products to the
concentration of its reactants at a certain temperature. A change in temperature results in a
change in Keq. For a reaction aA + bB ↔ cC + dD, the equilibrium constant expression is:
[𝐶]𝑐 [𝐷]𝑑
𝐾𝑒𝑞 =
[𝐴]𝑎 [𝐵]𝑏
Only species that can change concentration are included in the equilibrium constant expression.
This means that solids and pure liquids (the only liquid states in a reaction) are not included.
Note that the equilibrium constant expression is only applicable for reactions at equilibrium, not
reactions undergoing equilibrium shift.
K e q and temperature
Temperature is the only factor that affects the equilibrium constant. This fact can be used to
determine whether a reaction is exothermic or endothermic, provided the reaction’s equilibrium
constants at two different temperatures.
Gibbs free energy and equilibrium

Gibbs free energy can be related to a reaction’s equilibrium constant using the equation:
∆𝐺 ∅ = −𝑅𝑇 ln 𝐾𝑒𝑞
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Topic 8 & 18: Acids and Bases

8.1 Theories of acids and bases
Arrhenius acid/base: An H+/OH- donor.
Brønsted-Lowry acid/base: A proton donor/acceptor.
Acid-base conjugate pair: An acid and a base found

on opposite sides of a reaction that differ by a proton.
Acids can be categorized by how many protons they can donate:

Monoprotic – One e.g. HCl, HNO3
Diprotic – Two e.g. H2S, H2SO4
Triprotic – Three e.g. H3PO4, H3C6H5O7
Polyprotic – More than one. Polyprotic acids don’t donate all of their protons at once. All
of the first protons must be donated before second proton are donated.
Amphiprotic species: A species that can both accept and donate a proton. Species with an acidic
portion and a negative charge are definitely amphiprotic, though there are amphiprotic species
that aren’t negatively charged, such as water.
HCl (aq) + H2O (l) ↔ H3O+ (aq) + Cl- (aq) acting as acid
CO32- (aq) + H2O (l) ↔ HCO3- (aq) + OH- (aq) acting as base
NH3 isn’t amphiprotic, since it can’t really donate a proton to become NH2-.
8.2 Properties of acids and bases

Acids Bases
- Have a sour taste (e.g. citric acid) - Have a bitter taste (e.g. soap)
- Have a pH less than 7 - Have a pH greater than 7
- Turn litmus paper red (aciD → reD) - Turn litmus paper blue (Base → Blue)
- Keep phenolphthalein colourless - Turn phenolphthalein magenta
- Turn methyl orange red - Turn methyl orange yellow
Reactions of acids and bases:

acid + metal → salt + hydrogen acid + base → salt + water
2HCl (aq) + Zn (s) → ZnCl2 (aq) + H2 (g) HCl (aq) + NaOH (aq) → NaCl (aq) + H2O (l)
acid + metal carbonate → salt + carbon dioxide + water

2HCl (aq) + Na2CO3 (s) → 2NaCl (aq) + CO2 (g) + H2O (l)
Acids and bases are usually aqueous in solution, where they react with water to form H3O+
(hydronium) and OH- (hydroxide), respectively. Hydronium and hydroxide are responsible for
the acidic and basic properties of acids and bases, respectively. Since acids and bases dissociate
into ions, they can conduct electricity in solution.
40
8.3 The pH scale

pH (power of hydrogen): A method of representing the concentration of H3O+ in a solution.
𝑝𝐻 = −𝑙𝑜𝑔[𝐻3 𝑂+ ] [𝐻3 𝑂+ ] = 10−𝑝𝐻
𝑝𝑂𝐻 = −𝑙𝑜𝑔[𝑂𝐻 − ] [𝑂𝐻 − ] = 10−𝑝𝑂𝐻
pH and pOH values are composed of two parts: the integer before the decimal point
(characteristic) and the decimals after the point (mantissa). The characteristic is not counted as a
significant figure.
Auto-ionization of water
Water can undergo auto-ionization through the reaction
57.1 kJ + 2H2O (l) ↔ H3O+ (aq) + OH- (aq)
The concentrations of H3O+ and OH- at 25°C (298 K) are both 1.0 × 10-7 M. This causes the
charges of the ions to cancel out, leaving water neutral. Water’s equilibrium constant is K w:
𝐾𝑤 = [𝐻3 𝑂+ ][𝑂𝐻− ] = [1.0 × 10−7 ][1.0 × 10−7 ] = 1.0 × 10−14 𝑎𝑡 25℃

14.00 = 𝑝𝐻 + 𝑝𝑂𝐻 𝑎𝑡 25℃
−𝑙𝑜𝑔(𝐾𝑤 ) = 𝑝𝐾𝑤 = 𝑝𝐻 + 𝑝𝑂𝐻 𝑎𝑡 𝑎𝑛𝑦 𝑡𝑒𝑚𝑝𝑒𝑟𝑎𝑡𝑢𝑟𝑒
Due to the position of the enthalpy value, an increase in temperature shifts the equilibrium
towards the products and a decrease in temperature shifts it towards the reactants. Increasing
temperature can result in a maximum Kw value of 1.0 × 10-12 and decreasing temperature can
result in a minimum Kw value of 1.0 × 10-15.
Titration: An analytical technique used to determine the concentration of a sample of an acid or

base. The species in the burette, the titre, has a known concentration. The titre is added to a
species of unknown concentration until the sample is neutralized.
Equivalence point/Stoichiometric point: The point in a titration where the number of moles of
H3O+ equals the number of moles of OH- (not necessarily when moles of acid = moles of base).
8.4 Strong and weak acids and bases

Strong acid/base: An acid/base than completely dissociates in water, meaning its reaction will
progress to completion (i.e. →, not ↔).
Strong acids: HClO4, HI, HBr, HCl, HNO3, H2SO4 (but not HSO4-)
Strong bases: All alkali metals and OH-
Weak acid/base: An acid/base that forms an equilibrium (i.e. ↔) when dissociated, meaning it
doesn’t dissociate completely. Instead, [H3O+]/[OH-] is around 1000 times weaker than the
species’ initial concentration, making weak species less acidic/basic than strong species.
41
Determining the strength of an acid/base:

 Strong acids/bases have more extreme pH values, which can be seen using indicators.
Universal indicators gradually change colour over a pH value. Electronic pH proves can
also be used to measure pH.
 Strong species produce more ions than weak species, making them more conductive.
 Strong species have faster, more vigorous reactions.
Titrations cannot be used to determine pH because the amount of H3O+/OH- in a strong and
weak species of the same concentration is the same.
Enthalpy of neutralization
In strong-strong neutralizations, species completely dissociate, meaning the enthalpy of
neutralization depends only on the combination of H3O+ and OH-. All strong-strong
neutralizations have a ΔH value of -57.1 kJ/mol.
In strong-weak neutralizations, energy is required to shift the equilibrium towards full

dissociation, making the ΔH value of strong-weak neutralizations higher than -57.1 kJ/mol.
8.5 Acid deposition

Acid deposition: The formation of precipitation with a pH less than 5.6 in the atmosphere.
H2CO3: CO2 (g) + H2O (l) ↔ H2CO3 (aq)

H2CO3 (aq) + H2O (l) ↔ HCO3- (aq) + H3O+ (aq)
pH = 5.6 (normal for rain, not considered acid deposition or acid rain)
HNO3 & HNO2: N2 (g) + O2 (g) → 2NO (g) automobile engines

2NO (g) + O2 (g) → 2NO2 (g)
2NO2 (g) + H2O (l) → HNO3 (aq) + HNO2 (aq)
pH < 5.6 (considered acid rain)
H2SO3 & H2SO4: S (s) + O2 (g) → SO2 (g) mineral refining

2SO2 (g) + O2 (g) ↔ 2SO3 (g)
SO2 (g) + H2O (l) ↔ H2SO3 (aq)
SO3 (g) + H2O (l) ↔ H2SO4 (aq)
Acid deposition: Rain with a pH < 5.6 with a non-metal oxide.
18.1 Lewis acids and bases

Lewis acid/base: An electron pair acceptor/donor (electrophile/nucleophile). Due to their broad
definitions, Lewis acids and bases include species that aren’t normally acids and bases.
E.g. Boron trifluoride and ammonia
42
18.2 Calculations involving acids and bases

Acid/base dissociation constant (Ka/Kb): The Keq expression of a weak acid/base equilibrium.
HA (aq) + H2O (l) ↔ A- (aq) + H3O+ (aq) B (aq) + H2O (l) ↔ BH+ (aq) + OH- (aq)
[𝐴− ][𝐻3 𝑂+ ] [𝐵𝐻 + ][𝑂𝐻− ]

𝐾𝑎 = 𝐾𝑏 =
[𝐻𝐴] [𝐵]
For a conjugate acid-base pair, 𝐾𝑤 = 𝐾𝑎 × 𝐾𝑏 . The equation can be rearranged to find the
𝐾𝑤 𝐾𝑤
dissociation constant of any acid or base. (𝐾𝑎 = 𝐾𝑏
, 𝐾𝑏 = 𝐾𝑎
)
The stronger an acid, the larger its Ka value, the weaker its conjugate base, and the
smaller the Kb value of its conjugate base.
The stronger a base, the larger its Kb value, the weaker its conjugate acid, and the smaller
the Ka value of its conjugate acid.
When determining the pH of an amphiprotic species, the species’ reaction with water must be
determined first. This is done by comparing the Ka and Kb values of the species. Whichever
value is larger indicates the species’ nature in water.
Carbonate, CO32-, reacts with acids to form carbonic acid, H2CO3, which is unstable and breaks
down into carbon dioxide and water.
2HCl (aq) + Na2CO3 (aq) ↔ H2CO3 (aq) + 2NaCl (aq)
H2CO3 (aq) → CO2 (g) + H2O (l)
2HCl (aq) + Na2CO3 (aq) → CO2 (g) + H2O (l) + 2NaCl (aq)
18.3 pH curves
Buffer solutions
Buffer/Buffer system: A weak acid or base and its conjugate species in equilibrium, with the
conjugate species’ concentration increase such that it is similar to the concentration of the weak
acid or base. Buffers maintain a fairly constant pH in a solution by resisting changes in pH
caused by the addition of acids or bases.
A buffer system is prepared by adding the conjugate species (in salt form) to a solution
of a weak acid or base. Buffers can also be created by titrating a weak acid or base with its
conjugate species.
Buffers have a limit to their buffering effect, which is determined by the actual amount
of the weak species present in the solution. The maximum amount that can be buffered is the
buffering capacity. Dilution doesn’t affect the buffer itself, only its buffering capacity.
A buffer system’s pH depends on the conjugate pair used. If Ka > Kb, then the buffer is
acidic. If Ka < Kb, then the buffer is basic.
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Salt hydrolysis
Hydrolysis: The ionization of water that results from reaction with an ionic salt. Salt hydrolysis
occurs in neutralization reactions where the acid and base aren’t both strong. Strong-strong
neutralization produces a neutral salt.
Four cations react with water, meaning they act as acids: NH4+, Al3+, Fe3+, and Cr3+. These
cations can be produced through the dissociation of ionic compounds. In an acid table, they are
shown surrounded by six water molecules (e.g. [Al(H2O)6]3+ (aq)). The metal cation’s charge
pulls on the oxygen in water molecules, allowing them to donate a proton as an acid:
Al(H2O)63+ (aq) + H2O (l) ↔ Al(H2O)5(OH)2+ (aq) + H3O+ (aq)
Most anions react with water. If their salt has no hydrogens, the anion can be a weak
base. If the salt contains hydrogens, or if it is amphiprotic, the nature of the salt must be checked
by comparing Ka and Kb. Five anions don’t react with water. They are the conjugate bases of the
strong acids: ClO4-, I-, Br-, Cl-, and NO3-. Sulphuric acid’s conjugate base, HSO4-, doesn’t act as a
base to reform H2SO4, but does act as a weak acid.
pH curves
pH/Titration curve: A plot of pH vs. volume of titre added when the concentration of the
sample and the titre are known.
Strong-strong titration: When a strong acid is being

titrated with a strong base, the strong acid gives an
extremely low initial pH reading. There is a gradual rise in
pH as the titration approaches its equivalence point. The
sharp rise in pH at the equivalence point is called the
point of inflection of the curve. Once no acid remains to be
neutralized, the curve flattens and finishes at a high pH,
reflecting the strong base.
Strong-weak titration: When a weak acid is being titrated

with a strong base, the acid gives an initial pH reading
higher than that of a strong acid. The initial rise is steep
as the weak acid gets neutralized. However, as the acid
neutralizes, its conjugate base is formed, creating a buffer.
The curve rises sharply at the equivalence point, whose
pH value is determined by salt hydrolysis. Once no acid
remains, the curve flattens and finishes at a high pH.
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Weak-weak titration: Aren’t particularly useful, since their

point of inflection is less steep than that of other titrations.
Salts derived from a weak acid and a weak base will
undergo hydrolysis in water and the resulting pH of the
aqueous solution depends on the relative strengths of the
acid (Ka) and base (Kb).
Indicators
Indicator: A weak acid or base that changes colour as it shifts from reactant to product. Stronger
acids and bases cause the indicator’s equilibrium to shift when added to a solution. Each form
has a different colour. The colour seen depends on which side of the equilibrium is favoured.
HIn (aq) + H2O (l) ↔ In- (aq) + H3O+ (aq) Indicator acid form
Transition point: When [HIn] = [In-]. The colours of both forms are present, producing a
combination of the colours. The transition colour can be predicted using ROYGBIV.
Using a table of indicators:

 Different indicators have transition points throughout the pH range
 Indicators have a pH range over which they change colour
 Only colours outside the pH range may be referred to
 The transition point of an indicator is in the exact middle of the pH range
Since indicators are weak acids or bases, they have equilibrium expressions.
[𝐼𝑛− ][𝐻3 𝑂 + ]
HIn (aq) + H2O (l) ↔ In- (aq) + H3O+ (aq) 𝐾𝑎 = [𝐻𝐼𝑛]
At the transition point, [HIn] = [In-], yielding the equation Ka = [H3O+].
[𝐻3 𝑂+ ] = 𝐾𝑎
−𝑙𝑜𝑔 [𝐻3 𝑂+ ] = −𝑙𝑜𝑔 𝐾𝑎
𝑝𝐻 = 𝑝𝐾𝑎 𝑎𝑡 𝑡ℎ𝑒 𝑡𝑟𝑎𝑛𝑠𝑖𝑡𝑖𝑜𝑛 𝑝𝑜𝑖𝑛𝑡
When choosing an indicator for a titration, the indicator’s transition point should be at the
equivalence point of the neutralization reaction. For strong-strong titrations, phenolphthalein is
often used as an indicator, despite its pH range of 8.2-10.0. This is because one drop of the
strong acid/base titre can increase the solution’s pH from 7.0 to 8.2-10.0. Furthermore, the
titration can be narrowed down to one drop, unlike other indicators.
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Topic 9 & 19: Redox processes

9.1 Oxidation and reduction
Redox reaction: A reaction in which electrons are transferred from one species to another.
Redox reactions have a species that can donate electrons and a species that can accept electrons.
When writing redox equations, electron transfer, elements, and charge must be balanced.
Oxidation: Loss of electrons Reduction: Gain in electrons
LEO the lion goes GER (loss of electrons = oxidation, gain of electrons = reduction)
Oxidizing agent: A species that helps other species oxidize (by gaining electrons/reducing).
Reducing agent: A species that helps other species reduce (by losing electrons/oxidizing).
Oxidation number: The apparent charge of an atom in a free element, a molecule, or an ion.
When oxidizing, a species’ oxidation number becomes more positive. When reducing, it
becomes more negative.
 Neutral elements have an oxidation number of 0 (e.g. Na, Fe, O2)
 Ionic elements have an oxidation number equal to their ion’s charge (e.g. Mn5+ = +5)
 Hydrogen in a compound or polyatomic ion has an oxidation number of +1, except in
metal hydrides (i.e. when hydrogen is more electronegative than the metal it bonds
with), in which case it is -1. (e.g. H2O = +1, H2SO4 = +1, NaH = -1, MgH2 = -1)
 Oxygen in a compound or polyatomic ion has an oxidation number of -2, except in
peroxides, in which case it is -1. (e.g. H2O = -2, H2O2 = -1)
 The sum of a polyatomic ion’s oxidation numbers equals its charge.
Balancing redox reactions

Method 1 – Balancing half reactions – MAJOR OH-
1. Balance major atoms (not hydrogen and oxygen)
2. Balance oxygen using H2O
3. Balance hydrogen using H+
4. Balance charge using electrons
Method 2 – Oxidation number redox balancing

1. Assign oxidation states for each atom in the reactant and product species.
2. Deduce which species is oxidized and which species is reduced.
3. State the half-equation for the oxidation and reduction process.
4. Balance the half-equations so that # of electrons lost = # of electrons gained.
5. Add the two half-equations together to write the overall redox reaction.
6. Balance oxygen, hydrogen, and charge by adding H+ and H2O to the appropriate sides.
Disproportionation reaction: When a species reacts with itself as an oxidation and reduction
reaction. (e.g. 3ClO2- ↔ 2ClO3- + Cl-)
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Table of standard electrode potential: A table of reduction half reactions ordered by standard
electrode potential, Eθ(V). The more positive the Eθ(V) value, the more the half reaction favours
the reduced species (i.e. progress in direction written). The more negative the Eθ(V) value, the
more the half reaction favours the oxidized species (i.e. progress is opposite direction).
For a reaction to be possible, the reducing species must have enough strength to pull an
electron off of the oxidizing species. If more than one ion can react, the stronger
oxidizing/reducing reagent will be preferred (i.e. the pair furthest from each other).
Redox titration: A titration involving a redox reaction. Species that change colour when
oxidized or reduced can be used in redox titrations. For example, iodine, which reacts with
thiosulfate, changes from purple to pale yellow when reduced.
I2 (s) + 2e- ↔ 2I- (aq) 2S2O32- (aq) ↔ S4O62- (aq) + 2e-
Overall redox reaction: I2 (s) + 2S2O32- (aq) → 2I- (aq) + S4O62- (aq)
Acidified permanganate changes from purple to colourless when reduced.
MnO4- (aq) + 8H+ (aq) + 5e- ↔ Mn2+ (aq) + 4H2O (l)
Parts per million (ppm): A measure of concentration. As an example, the solubility of oxygen in
water at 0°C is 14.6 ppm.
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑐𝑜𝑚𝑝𝑜𝑛𝑒𝑛𝑡 𝑚𝑎𝑠𝑠 𝑖𝑛 𝑚𝑖𝑙𝑙𝑖𝑔𝑟𝑎𝑚𝑠
𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑖𝑜𝑛 𝑖𝑛 𝑝𝑝𝑚 = × 106 =
𝑡𝑜𝑡𝑎𝑙 𝑚𝑎𝑠𝑠 𝑣𝑜𝑙𝑢𝑚𝑒 𝑜𝑓 𝑠𝑜𝑙𝑢𝑡𝑖𝑜𝑛 𝑖𝑛 𝑙𝑖𝑡𝑟𝑒𝑠
The Winkler method

Winkler method: A method to determine the amount of dissolved oxygen in water.
Biochemical oxygen demand (BOD): The amount of oxygen required to oxidize an amount of
organic matter in five days at a set temperature. The BOD of pure water is 1 ppm.
As the amount of organic matter (i.e. pollution) in a sample increases, more oxygen is
required to oxidize it, meaning the sample has a higher BOD. High dissolved oxygen levels
indicates low pollution. This means that BOD is proportional to pollution.
Organic waste in water can be broken down by bacteria into other products through
aerobic digestion (i.e. requires oxygen). Without oxygen, bacteria produce different products
through the process of anaerobic digestion (i.e. no oxygen required).
Element in organic matter End product with O2 End product without O2

Carbon CO2 CH4
Hydrogen H2O H in other compounds
Nitrogen NO3- NH3
Sulphur SO42- H2S
Phosphorus PO43- PH3 (phosphine)
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9.2 Electrochemical cells

Electrochemical cell: A cell in which chemical energy-electrical energy conversions take place.
Voltaic cell: Cell that converts chemical to electrical energy through a spontaneous process.
Electrolytic cell: Cell that converts electrical to chemical energy with a non-spontaneous process.
Electrode: An electrical conductor used to make contact with a non-metallic part of a circuit. In
all electrochemical cells, oxidation takes place at the anode and reduction takes place at the
cathode. (AN OX CARED: anode-oxidation, cathode-reduction)
Voltaic cell (spontaneous) Electrolytic cell (non-spontaneous)

Cathode charge Positive Negative
Anode charge Negative Positive
Voltaic cells
A voltaic cell consists of two half-cells. Oxidation occurs at one half-cell (anode) and
reduction occurs at the other half-cell (cathode). Half-cells usually contain an aqueous metal ion
electrolyte and a long strip of the same metal as the electrode. A wire connects the two
electrodes together to allow for the flow of electrons. To complete the circuit, a salt bridge
(usually KNO3) is placed to link connect the electrolytes of the two half-cells together. The salt
bridge maintains the electrical neutrality of each half-cell. K+ and NO3- ions enter the half-cells to
compensate for the production or removal of ions from the electrolyte.
Cell diagram: A convention to represent a voltaic cell. The anode is written on the left and is
separated from the cathode by two parallel lines. E.g. Zn(s)|Zn2+(aq)||Cu2+(aq)|Cu(s)
19.1 Electrochemical cells

Electromotive force (EMF): Energy supplied by a source, divided by electric charge. Measured
in volts, which are equivalent to J/C (joule per coulomb).
Standard cell potential (Eθ): The potential difference between the anode and cathode of a cell
under standard conditions (25°C/298K, 100 kPa, 1.0 M solutions).
𝐸 𝜃 𝑐𝑒𝑙𝑙 = 𝐸 𝜃 𝑎𝑛𝑜𝑑𝑒 + 𝐸 𝜃 𝑐𝑎𝑡ℎ𝑜𝑑𝑒
When an electrode reaction is flipped, its Eθ switches signs. Eθ doesn’t change when an
electrode reaction is multiplied by a factor. If Eθcell is positive, the overall reaction is
spontaneous. If it is negative, the reaction is non-spontaneous. Eθ is also the maximum voltage
that can be delivered by a cell.
Standard hydrogen electrode (SHE): An inert platinum electrode in contact with 1.0 M H+
(usually through 1.0 M HNO3) and H2 gas at 100 kPa. SHE is used as a standard with which to
compare other electrodes. SHE has a Eθ value of 0 V at all temperatures.
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Nernst equation: ∆𝐺° = −𝑛𝐹𝐸 𝜃 , where ΔG° is Gibbs free energy, in joules
n is the number of moles of electrons transferred
F is Faraday’s constant (96,500 C/mol)
Eθ is standard cell potential
Note: Number of electrons transferred per species = change in species’ charge
Electrolytic cells
Electrolysis: The process by which electrical energy drives a non-spontaneous reaction. There
are three variations on electrolytic cells.
Electrolysis of a molten salt in a cell with inert electrodes: The only possible reactions that can
take place involve the molten salt ions. E.g. Molten NaCl electrolytic cell
Cl2 (g) + 2e- ↔ 2Cl- Na+ + e- ↔ Na (s)
2Cl- ↔ Cl2 (g) + 2e- Eθ = -1.36 V oxidation

2Na+ + 2e- ↔ 2Na (s) Eθ = -2.71 V reduction
2Na+ + 2Cl- → 2Na (s) + Cl2 (g) Eθ = -4.07 V overall
Electrolysis of an aqueous salt in a cell with inert electrodes: The oxidation and reduction
reaction of water need to be considered when determining the overall reaction. In electrolytic
cells with multiple possible oxidation-reaction combinations, the pair with the lowest difference
in voltage form the overall reaction that occurs. E.g. Electrolysis of aqueous NaBr
Oxidation H2O (l) ↔ ½O2 (g) + 2H+ (aq) + 2e- Eθ = -1.37 V

2Br- (aq) ↔ Br2 (l) + 2e- Eθ = -1.09 V
Reduction 2H2O (l) + 2e- ↔ H2 (g) + 2OH- (aq) Eθ = -0.77 V
Na+ + e- ↔ Na (s) Eθ = -2.71 V
2Br- (aq) + H2O (l) → Br2 (l) + H2 (g) + 2OH- (aq) Eθ = -1.86 V
Electrolysis of an aqueous salt in a cell with non-inert electrodes: The oxidation and reduction
reactions of the electrodes need to be considered, along with those of water. E.g. Electrolysis of
CuSO4 with a Cu anode and Fe cathode.
Oxidation 2SO42- (aq) ↔ S2O82- (aq) + 2e- Eθ = -2.01 V

H2O (l) ↔ ½O2 (g) + 2H+ (aq) + 2e- Eθ = -1.37 V
Cu (s) ↔ Cu2+ (aq) + 2e- Eθ = -0.34 V
Fe (s) ↔ Fe2+ (aq) + 2e- Eθ = +0.45 V
Reduction Cu2+ (aq) + 2e- ↔ Cu (s) Eθ = +0.34 V
2H2O (l) + 2e- ↔ H2 (g) + 2OH- (aq) Eθ = -0.77 V
Cu (s) + Cu2+ (aq) → Cu2+ (aq) + Cu (s) Eθ = 0.00 V
Iron, being the cathode (reduction), is unable to oxidize due to the electrons coming
from the power source. Instead, with a slight voltage, the copper anode begins to disintegrate
and a coating of copper appears on the cathode in a process called electroplating.
49
When electroplating, the object that is to be plated forms the cathode. The solution contains ions
of the metal that forms the coating. Ideally, the anode would also be composed of the coating
metal to prevent the depletion of ions.
Electrorefining: The refining of impure metals through the use of electrolysis. The cathode is
composed of a small amount of a pure metal, while the anode is composed of an impure
sample. Impurities that are more easily oxidized than the cathode oxidize into ions, but are
unable to reduce onto the cathode. Impurities that are less easily oxidized don’t oxidize at all
and fall off the anode. These impurities are usually metals such as gold, silver, or platinum.
To calculate the amount of a product that is produced in a certain amount of time: 𝑄 = 𝐼𝑡

Where Q is the charge in coulombs, I is the current in amperes, and t is the time, in seconds.
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Topic 10 & 20: Organic chemistry

10.1 Fundamentals of organic chemistry
Organic chemistry: The study of carbon-based compounds.
Catenation: The bonding of atoms of the same element (usually carbon) together into a chain.
Organic compounds Inorganic compounds

 Covalent or polar covalent bonds  Ionic or small covalent molecules
 Low melting/boiling point due to  High melting/boiling point for ionic
non-polarity (London dispersion) compounds (dipole-dipole, H-bond)
 Don’t conduct electricity (doesn’t  Conduct electricity (can dissociate
form ions) into ions)
 Can be extremely large  Limited to small molecules
 Can form chains (catenation)  Cannot form chains
 Usually have isomers  Usually don’t have isomers
 Comprise 96% of known compounds  Comprise 4% of known compounds
Functional group: A structure within a molecule that is responsible for its chemical properties.
Homologous series: A series of compounds with the same general formula and similar chemical
properties. Homologous series have gradually changing physical properties.
e.g. The boiling point of alkanes increases and the carbon chain lengthens due to
increasing intermolecular London dispersion forces.
Methane: -162°C Ethane: -89°C Propane: -42°C Butane: 0°C

Pentane: 36°C Hexane: 69°C Heptane: 98°C Octane: 126°C
Hydrocarbon: An organic compound containing only carbon and hydrogen.
Saturated compound: An organic compound where bonds between carbons are single bonds.
Unsaturated compound: An organic compound where at least one bond between carbons is a
double or triple bond. Does not include double or triple bonds to oxygen or nitrogen.
Aliphatic compound: An organic compound that is non-aromatic (i.e. no benzene ring).

Aliphatic compounds may be open-chain or cyclic, so long as there is no benzene.
Isomers: Molecules with the same molecular formula, but with different chemical structures.
Structural isomers: Molecules with the same number and type of atoms, but with different
structures, creating different compounds.
Positional isomers: Molecules with the same functional groups, but in different positions.
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Structural formulae of organic compounds

Fully expanded structure: All atoms and bonds are shown.
Normal/Regular structure: Atoms and their relative positions are shown, but bonds are
removed. May have lines between carbons.
Condensed formula: Side groups and extended chain lengths are placed in brackets. Each
bracketed portion is attached to the carbon before it.
CH3CH2CH2CH2CH2CH3 CH3(CH2)4CH3
Fully expanded structure Normal/Regular structure Condensed formula
Nomenclature of organic compounds

1. Determine the longest carbon chain, use its prefix.
2. Determine the lowest numbering for side chains Carbon chain prefixes
3. Order functional groups alphabetically by name 1 – meth- 2 – eth-
4. Separate numbers from each other by commas and 3 – prop- 4 – but-
number from letters by hyphens 5 – pent- 6 – hex-
5. Denote multiple instances of a functional group with 7 – hept- 8 – oct-
prefixes (e.g. di, tri, tetra, penta, hexa, hepta, octa, etc.) 9 – non- 10 – dec-
6. Give the highest priority functional group the lowest
numbering and the name ending
Functional groups
Alkanes: Hydrocarbons containing only saturated bonds. Name ending “ane”, general formula
CnH2n+2. Alkanes are non-polar due to small electronegativity differences and the cancelling of
charges by bond angles. A single-bonded carbon has a tetrahedral shape (109.5°).
Alkenes: Hydrocarbons containing at least one double bond. Name ending “ene”, general
formula CnHn. The double bonds are rigid, and cannot rotate. Alkenes can undergo addition
reactions. A double-bonded carbon has a trigonal planal shape (120°).
Alkynes: Hydrocarbons containing at least one triple bond. Name ending “yne”, general
formula CnHn-2. Triple bonds are more reactive than double bonds and can also undergo
addition reactions. A triple-bonded carbon has a linear shape (180°).
Cyclic compounds: Compounds containing a carbon ring. Instead of condensed formulae, cyclic
compounds use polygons. Cycloalkenes and cycloalkynes exist, but tend to break due to smaller
bond angles.
Cyclohexane: Cyclopentene:
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Alkyl halides (IB: Halogenoalkanes): Halogen side chains. Alkyl halides increase in reactivity
further down the group due to an increase in electron shells.
Fluorine – fluoro Chlorine – chloro Bromine – bromo Iodine – iodo
Aromatic compounds (Arenes): Compounds with a benzene ring, with side groups extending
outwards. “Aromatic” due to their sweet smell. Aromatic compounds are carcinogenic. The
benzene ring does not undergo addition reactions due to the delocalization of its electrons,
although its side groups undergo substitution reactions. Side groups may be named relative to a
group with position 1 using the prefixes ortho (position 2), meta (3), or para (4).
Alcohols (IB: Alkanols): An -OH group attached to a carbon. Name ending “ol”, prefix
“hydroxy”. All alcohols are toxic. An alcohol group isn’t acidic, meaning its hydrogen doesn’t
come off as an H+ ion. However, it does hydrogen bond.
Alcohols are soluble in water up to 3 carbons, after which the polar -OH group is
overshadowed by the non-polar hydrocarbon chain. Alcohols have higher melting/boiling
points than their alkane counterparts due to the hydrogen bonding of the alcohol group.
Aldehydes (IB: Alkanals): A carbon double-bonded to an oxygen (carbonyl group) at the end of
a carbon chain. Name ending “al”, written as a -CHO group. Aldehydes do not hydrogen bond,
but are quite polar, and have solubility and melting/boiling point trends similar to alcohols.
Ketones (IB: Alkanones): A carbon double-boned to an oxygen in the middle of a chain. Name
ending “one”. Ketones are polar at the oxygen, but only propanone is soluble in water.
Carboxylic acids (IB: Alkanoic acids): A carbon with an -OH group and a double-bonded
oxygen. Name ending “oic acid”. Carboxylic acids always occur at the end of a carbon chain.
Carboxylic acids are very polar and can donate an H+ ion.

When dissociated, they form negative ions. When not, they exhibit
hydrogen bonding. Carboxylic acids are soluble in water up to four
carbons. Two carboxylic acids can hydrogen bond to form a dimer.
Ethers: An oxygen single-bonded between two carbons. Name ending “oxy”. When named, the
shorter carbon chain that is bonded to the oxygen is visualized as a side group. Ethers are
slightly polar around the oxygen. Small ethers are somewhat soluble in water and very volatile,
often turning into gas at room temperature.
Amines: A nitrogen single-bonded to a carbon. Name ending “amine”, prefix “amino”.

Normally, the other two bonds are with hydrogen. If one of the hydrogens is replaced by a
carbon chain, it is treated as an alkyl group and uses the prefix “N”. Amines are weak bases,
meaning they can accept a proton (H+).
Nitriles: A carbon triple-bonded to a nitrogen. Name ending “anenitrile”, prefix “cyano”,

written as a -CN group.
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Amino acids
Organic compounds containing a carboxylic acid and an amine.
Amino acids can act as either acids or bases, depending on the pH

of the solution it is in. In neutral solutions, a proton is donated by the carboxylic acid portion of
the molecule to the amine portion. This creates a neutral molecule with a positive and negative
ion, called a zwitterion.
NH2−CH2−COOH ↔ NH3+−CH2−COO-
In acidic solutions, excess H+ ions bond with the -COO- portion. In basic solutions, the amine’s
extra proton is removed by OH- ions.
Acidic solutions NH3+−CH2−COO- + H+ ↔ NH3+−CH2−COOH
Basic solutions NH3+−CH2−COO- + OH- ↔ NH2−CH2−COO- + H2O
Two amino acids can join together when one acid’s acid portion reacts with the other acid’s
amine portion, forming an amide.
Esters
A combination of a carboxylic acid and an alcohol via a condensation reaction. The reaction
results in the ester group in the middle of the molecule with a water molecule being condensed
out. The condensation reaction requires concentrated H2SO4 and some heat. Esters have
pleasant smells, and are used in food scents and perfumes.
CH3−COOH + HO−CH2−CH3 → CH3COOCH2CH3 + H2O (ethyl ethanoate)
An ester’s name is that of the alcohol, with the name ending “anol” replaced with “yl”, followed
by the name of the carboxylic acid, with the “oic acid” name ending replaced with “oate”. Side
group numbering does not change, as functional groups are numbered away from the
carboxylic acid group. Esters are functional isomers of carboxylic acids.
Amides
A combination of a carboxylic acid and an amino acid via a condensation reaction. Naming
amides is similar to naming esters, except the “amine” name ending of the amine is removed,
and the carboxylic acid’s “oic acid” name ending is replaced with “amide”. Sometimes, an “N”
precedes the amine portion in the name.
CH3-CH2-COOH + H2N-CH2-CH3 → CH3CH2CONHCH2CH3 + H2O (N-ethyl propanamide)
Priority of functional groups

Carboxylic acids > … > Alkanes, ethers, alkyl halides
The order of other functional groups does not need to be memorized for the purposes of tests.
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Functional isomers
Compounds with the same molecular formula, but different functional groups. There are four
sets of functional isomers in the functional groups mentioned above:
1. Alcohols and ethers (e.g. ethanol & methoxymethane)

2. Alkenes and cycloalkanes (e.g. 1-pentene & cyclopentane)
3. Aldehydes and ketones (e.g. propanal & propanone)
4. Carboxylic acids and esters (e.g. propanoic acid & methyl ethanoate)
Primary, secondary, and tertiary compounds

In the case of halogenoalkanes and alcohols, the compound’s degree depends on the number of
carbons that are bonded to the carbon to which the functional group is bonded. For amines, the
compound’s degree depends on the number of carbons bonded to the nitrogen atom.
1° halogenoalkane 2° alcohol 3° amine
10.2 Functional group chemistry

Combustion of alkanes
All organic compounds have a combustion reaction with oxygen. If there is excess oxygen,
complete combustion occurs. If there is insufficient oxygen, incomplete combustion occurs,
producing carbon and carbon monoxide, along with carbon dioxide and water. Incomplete
combustion equations cannot be balanced.
Complete combustion: 2 C8H18 (l) + 25 O2 (g) → 16 CO2 (g) + 18 H2O (l)
Incomplete combustion: C8H18 (l) + O2 (g) → CO2 (g) + H2O (l) + C (s) + CO (g)
Halogenation of alkanes
The addition of a halogen to an alkane, creating a halogenoalkane. The halogenation of an
alkane requires the formation of free radicals through the breaking of a bond and the
distribution of its electrons. Depending on the electronegativities of the atoms that are split, the
bond’s electrons may be distributed in one of two ways:
Homolytic fission occurs when the two atoms have identical electronegativities, thereby
splitting the bond’s electrons evenly between the two atoms. This results in two neutral species
with a free radical. Homolytic fission occurs in carbon-carbon and halogen-halogen bonds.
CH3:CH3 → ∙CH3 + ∙CH3
55
Heterolytic fission occurs when the two atoms have different electronegativities,
resulting in the more electronegative atom acquiring both electrons. If carbon is more
electronegative, it gains both electrons, becoming a carboanion. If the other atom is more
electronegative, carbon loses its electron, becoming a carbocation.
H3C:H → :CH3- + H+ carboanion
H3C:Cl → CH3+ + :Cl- carbocation
The mechanism for the halogenation of an alkane is broken into three steps:
1. Initiation: The formation of a free radical through the homolytic fission of a diatomic
halogen. For chlorine, UV radiation provides enough energy for this.
Cl−Cl → ∙Cl + ∙Cl
2. Propagation: The paring of an alkane’s hydrogen with a halogen free radical, creating an
alkane free radical. The alkane free radical reacts with a diatomic halogen to create a
halogenoalkane and a new halogen free radical.
Cl∙ + H:CH2CH3 → HCl + ∙CH2CH3

Cl:Cl + ∙CH2CH3 → Cl:CH2CH3 + Cl∙
3. Termination: The joining of two free radicals to form a non-reactive molecule, which
isn’t listed as a main product of alkane halogenation. Three possibilities:
Cl∙ + Cl∙ → Cl2

Cl∙ + ∙CH2CH3 → ClCH2CH3
∙CH2CH3 + ∙CH2CH3 → CH3CH2CH2CH3 (butane)
Further halogens can be added to halogenoalkanes to create di-, tri-, and tetrahalogenoalkanes.
Addition reactions
The “adding” of a reactant molecule across a double or triple bond. Triple bonds can undergo
two addition reactions.
Halogenation: The adding of a diatomic halogen molecule. Halogenation is spontaneous at

room temperature. It can also be used to detect the presence of double and triple bonds in a
sample. If an alkene or alkyne is shaken in halogen water, the water decolourizes.
Br2 (l) + CH2=CH2 (g) → CH2Br−CH2Br (g)
Hydrohalogenation: The adding of a hydrogen halide (H−X, where X is a halogen).

Hydrohalogenation is spontaneous at room temperature.
H-Cl + CH2=CH2 → CH3−CH2Cl
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Hydrogenation: The adding of hydrogen gas. Hydrogenation isn’t spontaneous and requires
nickel as a catalyst, along with heat. Hydrogenation is generally used to change unsaturated fats
and oils into saturated fats and oils.
H2 (g) + CH2=CH2 (g) → CH3−CH3 (g)
Hydration: The adding of water (H−OH). Hydration is an equilibrium, with high pressure and
temperature (300°C) favouring the products. H3PO4 is a catalyst for the forward reaction.
H−OH (g) + CH2=CH2 (g) ↔ CH3−CH2OH (l)
Polymerization of alkenes
The formation of a polymer from several monomers, in this case, alkenes.
Addition polymerization: The reaction of monomers with a carbon-carbon double bond linking
together to form a polymer. Requires heat and pressure.
Cl∙ + CH2=CH2 → Cl−CH2−CH2∙

CH2Cl−CH2∙ + CH2=CH2 → CH2Cl−CH2−CH2−CH2∙
→ −[−CH2−CH2−]n− polyethene
The repeating sequence of the actual polymer is given in square brackets.
Oxidation of alcohols
The reaction of an organic compound with an alcohol group with an oxidizing agent. Two
common oxidizing agents used are dichromate (Cr2O72-) and permanganate (MnO4-), commonly
in the form of potassium dichromate and potassium permanganate. Both oxidizing agents
require acidic conditions (H+) to function. Primary, secondary, and tertiary alcohols have
different reactions.
Tertiary alcohols have no reaction, as there is no hydrogen bonded to the carbon for the
oxidizing agent to react with: CH3C(CH3)(OH)CH3 → No reaction
Secondary alcohols oxidize to form ketones: CH3CH(OH)CH3 → CH3COCH3
Primary alcohols oxidize into aldehydes, which can be further oxidized into carboxylic acids:
CH3−CH2−OH → CH3−CHO → CH3−COOH
These products can be separated. The aldehyde can be distilled because its lower
polarity compared to the alcohol and the carboxylic acid gives it the lowest boiling point. The
carboxylic acid can be isolated by condensing any evaporating aldehyde and returning it to the
chamber through refluxing, ensuring all aldehyde oxidizes into carboxylic acid.
Dichromate is orange in solution. After it is reacted, it produces Cr3+ ions, which are green. This
colour change in dichromate can be used in breathalyzers.
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20.1 Types of organic reaction

Nucleophilic substitution reactions
When a species in an organic compound, called the leaving group or substrate, is replaced by a
nucleophile. Abbreviated as “SN”.
Nucleophile: An electron-rich species that has a pair of electrons that it can donate to form a
bond. Common nucleophiles include OH-, NH3, and CN-.
The more electronegative leaving group pulls away from the carbon to which it was bonded,
taking with it both of the bond’s electrons. This makes the carbon more positive, allowing a
nucleophile to use its pair of electrons to form a bond in the place of the leaving group.
Nucleophilic substitution reactions occur in two ways, depending on whether the leaving group
(in our case, an alkyl halide) is primary, secondary, or tertiary.
SN1 reactions occur with tertiary halogens. The “1” in SN1 stand for “unimolecular” because
only one molecule (the halogenoalkane) is involved in the rate-determining step of the reaction.
As such, reaction rate is only due to the concentration of the species, and not the nucleophile.
A tertiary halogen is required because the carbons around the carbocation are needed to
stabilize it. This is accomplished through the inductive effect, where electrons are shifted
towards the positive charge in an attempt to cancel it out.
Before the leaving group is removed, the carbon has a tetrahedral shape. Once the
leaving group is removed, the carbocation that is formed is trigonal. This allows the nucleophile
to form a bond on either side of the trigonal plane, creating a 50/50 racemic mixture of the
possible enantiomers. This makes the resulting solution optically inactive.
SN2 reactions occur with primary halogens. The “2” in SN2 stands for “bimolecular” because
both the halogenoalkane and the nucleophile are responsible for the reaction rate. As such,
reaction rate is dependent on the concentration of both species.
The bulky halogen creates steric hindrance, which blocks the nucleophile and forces it to
“attack” the compound from the side opposite the halogen. The reaction inverts the molecule’s
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configuration, also known as Walden inversion. This makes SN2 reactions stereospecific,
meaning an optically active reactant will result in an optically active product.
An SN2 reaction with ammonia produces both a positive and a negative ion.
NH3 + CH3CH2Cl → CH3−CH2−C−NH2 + H+ + Cl-
An SN2 reaction with a cyanide ion produces a nitrile, which can, provided a nickel
catalyst and adequate heat, undergo a hydrogenation reaction to create a primary amine.
CN- + CH3CH2Cl → CH3−CH2−C≡N + Cl-
CH3−CH2−C≡N + 2 H2 → CH3−CH2−CH2−NH2
Secondary halogens under a process in between those for primary and tertiary halogens. For
testing purposes, they are not required.
S N 1 and S N 2 reaction rates

SN1 reactions have two steps – the ejection of the leaving group and the addition of the
nucleophile. This creates two energy peaks in the enthalpy diagram, with the peak associated
with the ejection of the leaving group being higher than that of the addition of the nucleophile.
As such, the ejection of the leaving group is the rate determining step of SN1 reactions.
SN2 reactions have one step, where the nucleophile collides with the substrate. This one step
determines the reaction rate.
There are three factors that affect the rate of nucleophilic substitution reactions:
1. Class of halogenoalkane: The reactivity of halogenoalkanes is 3° > 2° > 1°. As such, SN1
reactions are usually faster than SN2 reactions.
59
2. Type of halogen – bond strength and bond polarity
Type of bond Bond energy (kJ/mol) Electronegativity difference

C−F 484 4.0 – 2.1 = 1.9
C−Cl 338 3.0 – 2.1 = 0.9
C−Br 276 2.8 – 2.1 = 0.7
C−I 238 2.5 – 2.1 = 0.4
Based on electronegativity, fluorine would be the easiest to cleave heterolytically,

thereby increasing reactivity. However, it also has a high bond energy, which would
make it less reactive. Ultimately, bond strength is the determining factor of halogen
reactivity, making iodine the most reactive halogen and fluorine the least.
3. Choice of solvent: SN1 reactions are best performed in protic (hydrogen rich), polar
solvents, as the hydrogen prevents the nucleophile from attacking the compound before
the leaving group as ejected. SN2 reactions are best performed in aprotic (hydrogen
lacking), polar solvents, as the nucleophile can easily join the primary carbon.
Electrophilic substitution reactions

When an electrophile replaces another species on a compound. Electrophilic substitution is the
only benzene substitution reaction.
Electrophile: An electron poor species, typically with a positive charge. Electrophiles are
attracted to electron dense regions, such as double bonds.
An example would be the reaction between diatomic bromine and benzene. Br2 can gain
electrons to become electrophilic bromine ions. One bromine replaces a hydrogen on a benzene
ring, while the other bromine bonds with the hydrogen. FeBr 3 and AlBr3 are catalysts.
Another example is the nitration of benzene. This reaction requires a nitronium ion (NO2+),
which can be produced by a mixture of nitric acid and sulphuric acid at 50°C.
HNO3 + H2SO4 → HNO3 + H+ + HSO4- → NO2+ + H2O + HSO4-
The nitronium ion uses one of the benzene’s double bonds to bond itself to the molecule.
Benzene’s delocalized π-bonds stabilize the positive charge from the nitronium ion until the
hydrogen is ejected. This process also takes place with the CH3+ electrophile.
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Electrophilic addition reactions

When an electrophile bonds with an electron dense region of a compound.
Take the example of an alkene. Alkenes are trigonal planar around the carbons, leaving no steric
hindrance around the double bond. This makes it easy for an addition reaction to take place.
Hydrogen halides, halogens, and interhalogens (two or more different halogens) can all
perform electrophilic addition reactions. If the electrophile is polar, then the more positive
species is attracted to the double bond. Once the positive species is bonded to the compound, a
positive charge on the other carbon attracts the other half of the electrophile. If the electrophile
is non-polar, then the inductive effect repels the electrons of the electrophile species that is
closer to the double bond, giving it a slight positive charge.
In the case of longer alkenes, different products can form, depending on which carbon is
bonded to first. In these cases, Markovnikov’s Law applies.
CH2=CH−CH2−CH3 + HI → CH2I−CH2−CH2−CH3 or CH3−CHI−CH2−CH3
Markovnikov’s Law: When asymmetrical alkenes undergo

electrophilic addition, the electrophile bonds in the way that
forms the most stable positive ion. Therefore, 3° > 2° > 1°.
In the example above, this means that CH3−CHI−CH2−CH3

is the primary product, as the bonding of the hydrogen to
the left carbon produces a secondary carbon with a positive
charge. If hydrogen were to bond with the right carbon, a
primary carbon with a positive charge would be produced.
Reduction of carboxylic acids

The reverse of alcohol oxidation reactions. Carboxylic acids can be reduced to aldehydes, which
can be reduced into alcohols. Two common reducing agents, called Grignard reagents, are
LiAlH4 and NaBH4. Lithium aluminum hydride is stronger and can reduce both carboxylic
acids and aldehydes, while sodium borohydride can only reduce aldehydes.
CH3−CH2−COOH (+ LiAlH4) → CH3−CH2−CHO (+ LiAlH4 or NaBH4) → CH3−CH2−CH2−OH
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Conversion of benzene to phenylamine

1. Nitration of benzene at 50°C with H2SO4 (electrophilic addition) to create nitrobenzene
C6H6 + HNO3 (+ H2SO4) → C6H5NO2 (nitrobenzene) + H2O
2. Refluxing of nitrobenzene with concentrated HCl and Zn to produce phenylammonium
C6H5NO2 (l) + 3 Zn (s) + 7 H+ (aq) → C6H5NH3+ (aq) + 3 Zn2+ (aq) + 2 H2O (l)
3. Deprotonation of NH3+ using NaOH
C6H5NH3+ (aq) + OH- (aq) → C6H5NH2 (aq) + H2O (l)
20.2 Synthetic routes
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20.3 Stereoisomerism
Stereoisomers: Molecules with identical molecular formulae and bond structures, but different
spatial arrangements.
Geometric isomers
Isomers that differ by the position of groups across a double bond or above or below a ring
structure. Geometric isomers are denoted using cis-trans or E-Z notation.
In cis-trans notation, cis- denotes two groups on the same side, while trans- denotes two
groups on opposite sides (cis = same, trans = across). Trans isomers are more symmetrical and
tend to be non-polar, while cis isomers are polar due to the polar groups being on the same side.
Cis and trans isomers have slightly different melting/boiling points and may have different
chemical properties.
E-Z notation is similar to cis-trans notation. The more massive atom (i.e. higher atomic
number) on each double-bonded carbon is determined. If the two more massive groups are on
the same side, the bond has configuration Z (cis → ciZ). If they are on opposite sides, the bond
has configuration E.
Optical isomers (enantiomers)

Mirror-imaged molecules with the same four groups around a central carbon, called a chiral
carbon. Most amino acids have a chiral carbon between their amine and carboxylic acid.
Optical isomers have identical chemical and physical properties, but rotate plane polarized light
in opposite directions. A sample with only one enantiomer is optically active. Polarimeters can
measure how much each isomer rotates polarized light. A sample with both enantiomers
cancels their effects, becoming optically inactive. A 50/50 sample is called a racemic mixture.
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Only one type of enantiomer is produced in biological chemical reactions involving

enzymes due to the way an enzyme holds a substrate. This produces D (dextrorotary, right) and
L (levorotary, left) sugars and amino acids.
Conformational isomers
Molecules that differ by the rotation of single bonds. Conformational isomers can be
represented using Newman projections.
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Topic 11 & 21: Measurement and data processing
Topic 11 & 21: Measurement and data

processing
11.1 Uncertainties and errors in measurement and results
Precision: The closeness of multiple measurements to each other.
Accuracy: The closeness of a measurement to a standard or known value.
Significant figures: The number of digits of a given measurement. When multiplying or

dividing, the result should have the same number of significant figures as the least precise
measurement. When adding or subtracting, the result should have the same smallest decimal
place as the least precise measurement.
Experimental error: The degree of uncertainty associated with a measurement.

 Systematic error: A flaw in experimental design or with equipment used. Systematic
error implies that a measured value will always be greater than or less than the true
value, affecting accuracy. Systematic errors can often be reduced by adopting greater
care to the experimental design.
o Instrumentation error (e.g. faulty calibration of an instrument)
o Experimental methodology error (e.g. reading from the top of the meniscus)
o Personal error (e.g. the exact colour of a solution at its end point)
 Random error: Uncontrolled variables that cannot be eliminated, affecting precision.
Random errors can be reduced through repeated measurements. (e.g. estimating a
quantity between marked gradations on an instrument)
Absolute uncertainty: The margin of uncertainty associated with a measurement.

Relative uncertainty: The ratio of absolute uncertainty to the actual measurement.
When adding or subtracting, add absolute uncertainties. When multiplying or dividing,

add relative uncertainties.
11.2 Graphical techniques

Graphs communicate the effect of an independent variable on a dependent variable and
can lead to the determination of physical quantities.
Sketched graphs have labelled, but unscaled axes, and can show qualitative trends (e.g.
variables that are proportional or inversely proportional). Sketched graphs usually do not need
units, only the variables.
Drawn graphs have labelled and scaled axes, and are based on quantitative
measurements. Drawn graphs always display the appropriate units for variables.
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11.3 Spectroscopic identification of organic compounds

Degree of unsaturation/Index of hydrogen deficiency (IHD): A measure used to calculate the
number of rings and π-bonds in a compound. IHD doesn’t indicate anything about a
compound’s structure, only the presence of possible rings and multiple bonds.
 Double bond: 1 degree of unsaturation, or IHD = 1
 Triple bond: 2 degrees of unsaturation, or IHD = 2
 Carbon ring: 1 degree of unsaturation, or IHD = 1
 Benzene ring: 4 degrees of unsaturation, or IHD = 4
For an organic compound with a general formula CcHhNnOoXx (where X is a halogen),

𝐼𝐻𝐷 = 0.5(2𝑐 + 2 − ℎ − 𝑥 + 𝑛)
Infrared (IR) spectroscopy

IR energy can be absorbed by molecules and cause their bonds to
stretch or bend. Each bond has a characteristic energy at which it will
stretch or bend. IR absorbance is measured in values of 1/λ, called
wavenumber, which is given in cm-1.
Bonds in molecules can be thought of as springs (Hooke’s law):

 Atoms with a lighter mass vibrate at higher frequencies than those
with a heavier mass
 Triple bonds vibrate less than double bonds, which vibrate less than
single bonds
Molecules with multiple bonds can stretch and bend in different ways. For
an instrument to detect stretching and bending, the molecule’s dipoles
must change. If the dipoles are the same (e.g. H2, O2) or if they cancel each
other out (e.g. O=C=O), symmetric stretching will not be detected.
In IR spectroscopy, IR radiation of a gradually changing frequency is passed through a

sample. Energy of certain frequencies is absorbed, reducing the amount of radiation that passes
through the sample. The amount of radiation that passes through is the transmittance (%
transmittance). Different bonds have peaks in different ranges. The absence of a peak indicates
the absence of its associated bond.
Fingerprint region: The region below 1400 cm-1. Used to match the functional group aspects of
unknown compounds to those of known compounds.
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Proton nuclear magnetic resonance ( 1 H NMR) spectroscopy

When a magnetic field is applied to a sample, the spin of hydrogen protons in the sample either
align with the field or opposite to it. The difference between the two spin alignments is ΔE and
can be related to a frequency, ν, using the equation ∆𝐸 = ℎ𝜈
The frequency ν corresponds to a particular frequency of radio waves that can cause protons in
the sample to flip spin direction. ΔE depends on what its corresponding hydrogen is bonded to.
Different values of ΔE are detected and plotted on a spectrograph.
Environment: The number of neighbouring hydrogens to a target hydrogen and the way in
which they are bonded. Different environments can cause peaks to split.
Tetramethylsilane (TMS) is used as a standard in 1H NMR, being the assigned the value of 0
ppm. The distance between a peak and 0 ppm is chemical shift, δ.
Integration trace: The relative number of hydrogen atoms present.
Mass spectrometry (MS)

Mass spectrometers fragment organic molecules into smaller parts. Each fragment has its own
mass value. A mass spectrograph’s x-axis indicates mass-to-charge ratio (m/z ratio) and its y-
axis indicates relative abundance. Towards the low end of the scale, mass values represent
actual fragments, while the middle and high ends of the graph contain the parent compound
missing a fragment. The highest mass on the spectrum is the complete parent compound, called
the molecular ion. Mass spectrometry indicates the mass of the parts of a parent compound, but
doesn’t show how the fragments were connected.
21.1 Spectroscopic identification of organic compounds

High-resolution 1 H NMR spectroscopy
Spin-spin coupling: The effect of a hydrogen’s environment on its spectrograph reading. Spin-
spin coupling can be detected using high-resolution 1H NMR spectroscopy.
E.g. Ethanal (CH3−CH=O). Two peaks appear on the NMR spectrograph for ethanal – one for
methyl group (δ = 2.3) and one for the aldehyde hydrogen (δ = 9.6).
Ethanal’s methyl group has aldehyde hydrogen in its environment. If the aldehyde
hydrogen is aligned with the local magnetic field, it increases the strength of the field, causing
the peak of the methyl group to move further away from 0 ppm. It the aldehyde hydrogen is
aligned opposite to the field, it weakens the field, shifting the peak closer to 0 ppm.
Ethanal’s aldehyde hydrogen has the three hydrogens in the methyl group in its
environment. The three hydrogens have a series of possible orientations in the magnetic field:
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All 3 aligned align|align|align 1 possibility

against|align|align
2 aligned, 1 against align|against|align 3 possibilities
align|align|against
align|against|against
2 against, 1 aligned against|align|against 3 possibilities
against|against|align
All 3 against against|against|against 1 possibility
The four possible sets of alignment results in four peaks for the aldehyde hydrogen.
However, since the middle two possibilities are 3 times more likely than the outer two
possibilities, they will be 3 times more intense on the spectrograph.
n+1 rule: A hydrogen type with n hydrogens in its environment has n + 1 neighbouring peaks
caused by peak splitting. The relative intensity of the peaks can be deduced from Pascal’s
triangle.
TMS is a silicon atom with four methyl groups, giving it a tetrahedral shape. TMS has certain
properties:
 All hydrogens have the same environment, meaning no peak splitting
 The methyl groups are bonded to silicon, not carbon, meaning less energy is required to
flip a proton’s spin. This places TMS’s peak outside the range of carbon compounds.
Single-crystal X-ray crystallography

X-rays are sent through a sample as a beam. Upon contact with the atoms of the sample crystal
molecule, they diffract. The diffracted rays produce a characteristic pattern that gives
information about various aspects of the compound, such as bond length, bond angle, and the
arrangement of atoms next to each other.
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Option C: Energy
Option C: Energy
C.1 Energy sources
A good energy source contains a large amount of potential energy that is converted to a useful
form at a reasonable rate, with minimal pollution and unwanted products.
All energy conversions disperse energy as heat, resulting in a degradation in energy quality.
Less efficient fuels degrade in quality more.
𝑢𝑠𝑒𝑓𝑢𝑙 𝑜𝑢𝑡𝑝𝑢𝑡 𝑒𝑛𝑒𝑟𝑔𝑦
𝑒𝑛𝑒𝑟𝑔𝑦 𝑡𝑟𝑎𝑛𝑠𝑓𝑒𝑟 𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑐𝑦 = × 100%
𝑡𝑜𝑡𝑎𝑙 𝑖𝑛𝑝𝑢𝑡 𝑒𝑛𝑒𝑟𝑔𝑦
Measures of fuel quality:
Energy density: A measure of fuel quality by energy stored per unit volume.
Specific energy: A measure of fuel quality by energy stored per unit mass.
𝑒𝑛𝑒𝑟𝑔𝑦 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑏𝑦 𝑓𝑢𝑒𝑙 𝑒𝑛𝑒𝑟𝑔𝑦 𝑟𝑒𝑙𝑒𝑎𝑠𝑒𝑑 𝑏𝑦 𝑓𝑢𝑒𝑙
𝑒𝑛𝑒𝑟𝑔𝑦 𝑑𝑒𝑛𝑠𝑖𝑡𝑦 = 𝑣𝑜𝑙𝑢𝑚𝑒 𝑜𝑓 𝑓𝑢𝑒𝑙 𝑐𝑜𝑛𝑠𝑢𝑚𝑒𝑑 𝑠𝑝𝑒𝑐𝑖𝑓𝑖𝑐 𝑒𝑛𝑒𝑟𝑔𝑦 = 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑓𝑢𝑒𝑙 𝑐𝑜𝑛𝑠𝑢𝑚𝑒𝑑
Renewable energy source: A naturally replenished energy source.

Non-renewable energy source: A finite energy source.
C.2 Fossil fuels

Fossil fuels are formed by the reduction (addition of hydrogen) of biological compounds
containing carbon, hydrogen, oxygen, nitrogen, and phosphorous. Since C−H and C−C bonds
are the strongest, they remain after the other bonds have broken.
Crude oil
Crude oil, or petroleum, contains a large
mixture of hydrocarbons of varying chain
lengths. Longer hydrocarbons have
stronger van der Waals forces, meaning
they have higher melting/boiling points.
This property can be used to separate
crude oil into “fractions” or different chain
lengths using fractional distillation.
In fractional distillation, crude oil is heated

and placed in the bottom of a fractionating
column. Temperatures decrease as one
ascends the fractionating column. As such,
the dark, viscous, long-chain hydrocarbons
condense near the bottom, while shorter-
chain hydrocarbons condense near the top.
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Option C: Energy
Shorter-chain hydrocarbons are more volatile and make for better fuels than longer-
chain hydrocarbons. They also burn with a cleaner flame. However, there are far more long-
chain hydrocarbons than short-chain hydrocarbons. As such, cracking is used to create more
short-chain hydrocarbons.
In cracking, fractions that contain long-chain hydrocarbons are heated over a catalyst,
causing the hydrocarbons to break up into smaller hydrocarbons.
Octane rating and catalytic reforming

Octane rating: A measure of a fuel’s ability to resist auto-ignition. 2,2,4-trimethylpentane has an
octane rating of 100, while heptane has an octane rating of 0. A fuel with an octane rating of n
can be said to have the same tendency to auto-ignite as a mixture of n% 2,2,4-trimethylpentane
and (100-n)% heptane. Octane ratings of less than 0 and more than 100 are possible.
The higher the octane rating, the less likely a fuel is to auto-ignite. Auto-ignition is an
important issue for engines because it can cause engine knocking, which damages the engine.
The octane rating of a fuel is affected by three factors:

- Branching: More branching results in a higher octane rating
- Chain length: Longer carbon chains result in lower octane ratings
- Compound type: Aromatics have a higher octane rating than straight- and branched-
chain alkanes with the same number of carbons
Gasoline is a mixture of many different straight- and branched-chain alkanes (aliphatics), cyclic
alkanes, and aromatics, but contains no alkenes. Gasoline is composed of approximately 50%
aliphatics and 20-30% each of cyclic alkanes and aromatic compounds.
Catalytic reforming: The conversion of low-octane number alkanes to higher-octane number

isomers. By heating straight-chain alkanes with a platinum catalyst, chains break and reform,
increasing the proportion of branched alkanes. The products are passed over zeolite, which acts
as a molecular sieve catalyst and separates the branched and unbranched alkanes.
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Option C: Energy
Using platinum in conjunction with aluminum oxide or another metal catalyst can
dehydrogenate alkanes into aromatic compounds:
Reforming: The summative effect of several reactions occurring simultaneously, used to

produce high-octane alkanes and useful aromatics.
Coal gasification and liquefaction

Coal gasification: The production of hydrocarbons in the form of synthesis gas (also called coal
gas or syngas) from coal. Coal reacts with oxygen and steam in a gasifier. The supply of oxygen
is limited, preventing the coal from combusting. Pollutants are then removed from the gas.
Coal gasification can occur underground, eliminating the cost of building and
maintaining a gasifier and preventing carbon dioxide from being released into the atmosphere.
Underground coal gasification is an example of carbon capture and storage (CCS).
Process of coal gasification:

1. Pyrolysis: Coal is degraded into gases and a charcoal-like substance, called char. Due to
inadequate oxygen for combustion, partial oxidation takes place, generating compounds
like carbon monoxide and carbon dioxide.
coal → CH4 + H2O + C + H2 + CO + CO2 + various hydrocarbons
2. Reduction: Synthesis gas (mainly CO and H2) is produced.

C + H2O → CO + H2 CO + 3H2 → CH4 + H2O
C + CO2 → 2CO CO + H2O → CO2 + H2
3. Clean-up: Desired products are purified and removed. Remaining char is burnt off and
CO2 and impurities can be removed and stored underground.
C + O2 → CO2
Gasification can also be carried out with wood or other biomass materials, not just coal.
Coal liquefaction: The adjustment of the carbon-to-hydrogen ratio of synthesis gas or coal to
produce synthetic liquid fuels through the Fischer-Tropsch process:
nCO + (2n + 1)H2 → CnH(2n + 2) + nH2O
Direct coal liquefaction (DCL): The addition of H2 to heated coal in the presence of a catalyst.
Indirect coal liquefaction (ICL): The addition of water or carbon dioxide to syngas over a
catalyst.
71
Option C: Energy
Coal isn’t required to produce synthetic liquid. Biofuels can also be used to produce synthesis
gas, which can then be turned into synthetic liquid using indirect coal liquefaction.
E.g. CH4 + H2O → CO + 3H2
Carbon footprint: The net quantity of carbon dioxide produced by a reaction, generally
expressed in tons of carbon dioxide.
C.3 Nuclear fusion and fission

Mass defect: The difference between a nucleus’ mass and the sum of the masses of its nucleons.
Binding energy: The energy required to separate a nucleus into its constituent parts.
Nuclear fusion: The reaction between two or more atomic nuclei to form a larger nucleus,
converting any mass defect into binding energy. Nuclear fusion is possible so long as the
binding energy per nucleon increases. Since iron has the highest binding energy per nucleon,
nuclear fusion is not possible past iron.
E.g. 21𝐻 + 31𝐻 → 42𝐻𝑒 + 10𝑛
Nuclear fusion is a promising energy source due to its cheap and abundant fuel and lack
of radioactive waste. The vast majority of the Universe’s fusion reactions take place in stars. As
the products of fusion reactions cool and leave a star’s atmosphere, electrons in their atoms emit
electromagnetic radiation of specific wavelengths. By observing a star’s spectra, scientists are
able to deduce its composition.
Nuclear fission: The splitting of a large nucleus into two smaller nuclei, converting mass defect
to energy. Nuclear fission generates nuclear waste, which must be disposed of safely. Spent
nuclear fuel is kept in long-term storage, encased in steel and surrounded by inert gas, which is
then covered in concrete and buried.
Critical mass: The amount of material needed to sustain a reaction.
Types of subatomic particle:

Alpha particle: α or 42𝐻𝑒 Neutron: 10𝑛
Beta particle: β or −10𝑒 Proton: 11𝑝 or 11𝐻
Gamma particle: γ or 00𝛾 Positron: +10𝛽 +
Transmutation: The conversion of one element to another by capturing or emitting a particle.
Half-life (t1/2): The time it takes for half of the particles of a sample to decay.
ln 2
𝑡1/2 = 𝑡 𝑁 𝑁0 = 𝑁 × 2# 𝑜𝑓 ℎ𝑎𝑙𝑓−𝑙𝑖𝑣𝑒𝑠 𝑝𝑎𝑠𝑡
ln( 0 )
𝑁
Where N0 is the initial amount of a radioactive sample

N is the remaining amount of the sample
t is the time elapsed
72
Option C: Energy
C.4 Solar energy

Photosynthesis: The process by which plants convert light energy into chemical energy.
Sunlight is absorbed in chloroplasts by chlorophyll.
Chlorophyll is capable of absorbing visible light due to its conjugated structure of

alternating single and multiple bonds. If there were no conjugated structure, electron would
absorb ultraviolet light instead. An electron in chlorophyll is returned to its ground state after
being excited through a series of chemical reactions that results in the following net equation:
6CO2 + 6H2O → C6H12O6 + 6O2
Plant pigments aside from chlorophyll are also coloured due to their conjugated
systems. For example, violets are blue because the conjugation of anthocyanin absorbs longer
wavelengths of visible light.
Biofuels
Biofuel: A fuel produced through a biological, rather than geological, process. For example,
ethanol can be produced from glucose using fermentation:
C6H12O6 → 2C2H5OH + 2CO2
Although carbon dioxide is produced by the fermentation process, it is balanced by the

plant consuming CO2 for photosynthesis. As such the ethanol produced is carbon neutral.
Biodiesel: A substitute for diesel, derived from vegetable oil. Due to large intermolecular forces,
vegetable oils are very viscous and undergo incomplete combustion, causing damage to
engines. To prevent this, vegetable oils can be converted into esters with weaker intermolecular
forces through the process of transesterification:
A similar process can be used to produce short-chain esters from long-chain esters and
shorter-chain alcohols, using a strong acid or base as a catalyst:
RCOOR’ + R”OH → RCOOR” + R’OH catalyst: H+ or OH-
A base catalyst deprotonates the alcohol. The smaller alkyl group from the alcohol
replaces the larger alkyl group, producing a less viscous and more volatile ester.
73
Option C: Energy
Advantages of biodiesel Disadvantages of biodiesel

- High flash point (less flammable) - More viscous, requires pre-warming
- Smaller carbon footprint due to plants - Slightly lower energy content
consuming CO2 to grow - Uses agricultural resources, causing
- More easily biodegradable in the case increased food prices globally
of an oil spill - Biodiesel production more expensive
- No sulfur, meaning no SO2 emissions - Higher levels of nitrogen, meaning
- Sustainable, if derived from plants more nitrogen oxides when burned
- Good solvent − cleans engines - Dirt cleaned from engine tends to clog
fuel filters, causing stalling
- Can dissolve paint and protective
coatings
C.5 Environmental impact – global warming

Greenhouse effect: The trapping of infrared radiation by greenhouse
gases (e.g. CO2, CH4, H2O) in the atmosphere. The highest frequencies of
light are absorbed by the atmosphere upon entry, allowing infrared,
visible, and ultraviolet light to pass through. Upon passing through, the
light is absorbed by the Earth’s surface and re-emitted as IR radiation.
Infrared radiation causes the covalent bonds in greenhouse gas

molecules to bend and stretch. This is because the natural frequencies of
bending and stretching greenhouse gases are also the frequencies of
infrared radiation. Some stretching and bending changes the dipole
moment of the molecule, causing an accentuation of the molecule’s polar
properties, which can be detected using infrared spectroscopy.
95% of the greenhouse gases in the atmosphere is water vapour, the vast majority of
which is of natural origin. As temperatures rise, more surface water evaporates, increasing
atmospheric water vapour levels. Although this initially warms the planet, much of the water
vapour condenses into clouds, which blocks sunlight and cools the Earth. As such, the amount
of water vapour in the atmosphere has remained roughly the same and is self-regulating.
Anthropogenic greenhouse gases come from three main sources:

1. The burning of fossil fuels. Carbon dioxide, previously stored underground in
hydrocarbons, is released into the atmosphere by combustion. Account for nearly 50% of
anthropogenic greenhouse gases.
2. The production of industrial gases in factories. Produces not only CO2, but new GHGs,
such as nitrogen oxides (NOx). Accounts for about 25% of anthropogenic GHGs.
3. Agriculture, through the generation of methane by animals, and deforestation, through
the cutting down of trees. Agriculture and deforestation contribute near equal amounts
to the remaining 25% of anthropogenic GHGs.
74
Option C: Energy
Carbon sink: A reservoir that stores carbon in the form of chemical compounds for an indefinite
period of time. Carbon sinks remove about half of all anthropogenic CO2 from the atmosphere.
Approximately 30% of anthropogenic CO2 is absorbed by the oceans. Since carbon

dioxide isn’t very soluble, the only exchange takes place on the ocean surface. CO2 gas is turned
into aqueous CO2, which is then turned into carbonic acid:
CO2 (g) ↔ CO2 (aq) CO2 (aq) + H2O (l) ↔ H2CO3 (aq)
The overall process is slightly exothermic, meaning an increase in temperature favours

the reactants and decreases the ability of CO2 to dissolve in water.
Since carbonic acid is a Brønsted-Lowry acid, it releases protons in water, causing the
following equilibrium reactions:
H2CO3 (aq) + H2O (l) ↔ H3O+ (aq) + HCO3- (aq)
HCO3- (aq) + H2O (l) ↔ H3O+ (aq) + CO32- (aq)
The acidity of water therefore reflects the extant of the reactions:
Measures to reduce greenhouse gas emissions

Methods of reducing GHG emissions in industry and energy production:
- Carbon capture and storage (CCS): The process of capturing waste CO2, transporting it
to a storage site, and storing it so that it does not enter the atmosphere.
- Scrubbing: The removal of SO2 from coal power plant emissions. Water and limestone
react with SO2 to form gypsum, also called calcium sulfate hydrate (CaSO4 ∙ 2H2O).
- Sequestration: The conversion of carbon dioxide to a carbonate using a silicate.
e.g. Mg2SiO4 (s) + 2CO2 (g) → 2MgCO3 (s) + SiO2 (s)
- Carbon recycling: The use of carbon dioxide as a feedstock for synthetic fuels.
- Use of carbon-neutral fuel alternatives, such as synthesis gas.
75
Option C: Energy
Methods of reducing GHG emissions in agriculture and deforestation:

- Land use and recycling: A method of reducing agriculture’s footprint.
- Crop rotation: Increases carbon capture and storage by the soil and reduces emissions,
compared to nitrogen-based fertilizers.
- Deforestation to create agricultural land: Should be carbon neutral, provided fertilizer
use is not increased.
- Use of urban space to grow crops: Reduces transport emissions and costs.
Global dimming: The cooling of the Earth’s surface caused by the reflection of sunlight into
space by smoke, dust, and clouds. Particulate matter in the atmosphere can cause water
droplets to form (nucleate), which then collect to form clouds. These polluted clouds reflect
more light than non-polluted clouds. Due to these processes, fossil fuel pollutants both decrease
and increase global warming.
Harmful effects of global dimming:

- Acid rain caused by certain types of pollutants
- Decrease in evaporation rate of water, leading to weaker monsoons and a reduction in
crop yields in certain parts of the world
- Local health problems (e.g. asthma)
C.6 Electrochemistry, rechargeable batteries and fuel cells

Battery: A series of portable electrochemical cells.
Primary electrochemical cell: A cell in which materials are consumed and the reaction is not
reversible. As such, either the cell’s anode, electrolyte, or both must be replaced or the battery
must be thrown out entirely. Primary cells typically degrade because the anode is oxidized.
Furthermore, travelling ions polarize the cell, stopping the reaction and building up hydrogen
bubbles on the anode. These bubbles increase the cell’s internal resistance and reduce its output.
Primary cells are best suited for low-current, long-storage devices, such as smoke detectors.
Secondary electrochemical cell: Also called a rechargeable battery, a cell whose chemical
reactions can be reversed through the application of an electric current. Secondary cells are
better than primary cells at meeting strong current demands, such as those of a phone or an
electric car. However, they also have higher rates of self-discharge.
Secondary cells: Lead-acid batteries

Lead-acid batteries are the typical car battery. Electrical energy from the battery is used to start
ignition. Energy from the combustion of gasoline is then used to recharge the battery while
driving. As such, extended idling will drain the battery due to self-discharge.
A lead-acid battery’s electrolyte is sulfuric acid, which, being a strong acid, exists in
solution as H+ (aq) + HSO4- (aq). The following reactions take place during discharge:
76
Option C: Energy
Anode Pb (s) + HSO4- (aq) → 2PbSO4 (s) + H+ (aq) + 2e-

Cathode PbO2 (s) + 3H+ (aq) + HSO4- (aq) + 2e- → PbSO4 (s) + 2H2O (l)
Cell Pb (s) + PbO2 (s) + 2H+ (aq) + 2HSO4- (aq) → 2PbSO4 (s) + 2H2O (l)
The above reactions are reversed when charging.
Anode Electrolyte Cathode

Fully charged battery Pb (s) H2SO4 (aq) PbO2 (s)
Discharged battery PbSO4 (s) dilute H2SO4 (aq) PbSO4 (s)
Continual charging produces some overvoltage, which produces hydrogen and oxygen through
the electrolysis of water. As such, some non-sealed lead-acid batteries require occasional
topping up with water.
Secondary cells: Lithium-ion batteries

Lithium-ion batteries have an anode composed of lithium absorbed in a lattice of graphite
electrodes and a lithium cobalt oxide complex (LiCoO2) cathode. When discharged, lithium
atoms in the anode oxidize into lithium ions and migrate through the electrolyte to the cathode.
When charging, lithium ions migrate back to the anode and are reduced back to lithium atoms.
Charging reaction Discharging reaction

Anode Li+ + e- → Li (s) Li (s) → Li+ + e-
Cathode LiCoO2 (s) → Li+ + e- + CoO2 (s) Li+ + e- + CoO2 (s) → LiCoO2 (s)
Due to lithium’s reactivity with water, the electrolyte must be non-aqueous, usually a
gel polymer. Since lithium is extremely lightweight and has the highest oxidation potential of
any element, it makes lithium-ion batteries ideal lightweight batteries.
Advantages of lithium-ion batteries: Disadvantages of lithium-ion batteries:

- Very high charge specific density - Sensitive to high temperatures
- Hold charge better than other - Damaged if allowed to run
batteries completely flat
- Can withstand many recharge cycles - Lasts only a few years
- No heavy metals, meaning safer - Can explode if punctured or
disposal overheated
Secondary cells: Nickel-cadmium batteries
Nickel-cadmium (NdCd) rechargeable cell: A battery with a nickel (III) oxide hydroxide
cathode and a cadmium metal anode.
Charging reaction
Anode Cd(OH)2 (s) + 2e- → Cd (s) + 2OH- (aq)
Cathode 2Ni(OH)2 (s) + 2OH- (aq) → 2NiO(OH)2 (s) + 2H2O (l) + 2e-
77
Option C: Energy
Discharging reaction
Anode Cd (s) + 2OH- (aq) → Cd(OH)2 (s) + 2e-
Cathode 2NiO(OH)2 (s) + 2H2O (l) + 2e- → 2Ni(OH)2 (s) + 2OH- (aq)
The solid hydroxides remain deposited on the electrodes, leaving the hydroxide ions to
move through the solution. This gives the cell a low internal resistance.
Advantages of NiCd batteries: Disadvantages of NiCd batteries:

- Low internal resistance means a quick - High cost
recharge time - Use of cadmium (heavy metal)
- Can undergo full discharge without - Quickly lose charge at high
damage temperatures
Voltage and internal resistance

Voltage: The difference in electric potential between two points. In a battery, these two points
are the anode and cathode. Voltage can be increased by placing cells in series. Other factors that
affect voltage include the nature of the materials, the mass and surface area of the electrodes,
and the specific energy density of the materials.
Internal resistance: The resistance within a battery. Depends on ion mobility, electrolyte
conductivity, and electrode surface area.
At lower temperatures, reactions slow down, reducing ion mobility and increasing
internal resistance. At higher temperatures, internal resistance is lower, but rates of self-
discharge increase.
Hydrogen fuel cells

Fuel cell : An electrochemical device that converts chemical potential energy from a fuel into
electrical energy. In hydrogen fuel cells, the fuel is hydrogen, which is oxidized by oxygen to
produce water. As such, no pollution is produced, making hydrogen fuel cells very efficient.
Proton exchange membrane (PEM) fuel cell : A

hydrogen fuel cell in which the electrolyte or
separator is a proton exchange membrane. The PEM
is a polymer that allows H+ ions to diffuse through,
but not electrons or molecules, essentially
functioning as a salt bridge.
Hydrogen is oxidized at the anode and oxygen is reduced at the cathode:

Anode: H2 → 2H+ + 2e- Cathode: O2 + 4e- → 2O2- Cell: 2H2 + O2 → 2H2O
78
Option C: Energy
Alkali fuel cell: A hydrogen fuel cell with an

alkaline electrolyte, usually potassium hydroxide.
OH- ions migrate towards the anode, reacting with
H+ ions to form water. Alkali fuel cells are slightly
different from PEM fuel cells. In PEM fuel cells,
water is formed at the cathode, while in alkali fuel
cells, water is formed at the anode.
Although oxygen can be obtained from air, the hydrogen must be extremely pure, usually
necessitating expensive catalysts impregnated on graphite electrodes. There are two main
sources of hydrogen:
1. Hydrolysis of water, producing clean hydrogen

2. Reforming hydrocarbons or biofuels. For example, coal gasification or the conversion of
methane into synthesis gas. Hydrocarbons are reacted with steam to produce carbon
monoxide and hydrogen:
CxHy + xH2O → xCO + (y/2 + x)H2
Some carbon dioxide may by produced. The hydrogen must be isolated and purified
before it can be used. Although the process is endothermic, requiring energy, it uses a
renewable fuel source and is about 70% efficient. This method produces roughly 85% of the
hydrogen used in fuel cells.
Direct methanol fuel cell: A fuel cell that uses methanol to provide H+ ions. Direct methanol fuel
cells have the same components as a PEM fuel cell.
Anode CH3OH + H2O → 6H+ + 6e- + CO2
Cathode 3/2 O2 + 6H+ + 6e- → 3H2O
Cell CH3OH + 3/2 O2 → CO2 + 2H2O
The reaction in the anode needs water, so a solution of 1M methanol is normally used.
This lowers the energy density, but it is still higher than that of hydrogen. However, the
production of carbon dioxide makes direct methanol fuel cells less clean than PEM fuel cells.
Direct methanol fuel cells operate at around 120°C, compared to the PEM fuel cell’s 80°C. Direct
methanol fuel cells also require more catalyst.
Fuel source Energy density (MJ/L) Specific energy (ML/kg)

Compressed hydrogen 1.9 120
Methanol 16 20
Liquified natural gas 21 50
Liquid propane 27 46
Gasoline 32 46
79
Option C: Energy
Although hydrogen has the highest specific energy, it occupies a greater volume than methanol,
even when compressed. Furthermore, hydrogen requires regulators and compressors, which
add additional weight.
Calculations for electrochemical cells

Thermodynamic efficiency: The ratio of Gibbs energy change to enthalpy change. Fuel cells may
not operate at maximum efficiency due to internal resistance caused by poor ion mobility or
reduced electrolyte conductivity.
∆𝐺 −𝑛𝐹𝐸 𝜃
𝑡ℎ𝑒𝑟𝑚𝑜𝑑𝑦𝑛𝑎𝑚𝑖𝑐 𝑒𝑓𝑓𝑖𝑐𝑖𝑒𝑛𝑐𝑦 = = (unit 19.1)
∆𝐻 ∆𝐻
Nernst equation: An equation used for calculating the potential of an electrochemical cell under
non-standard conditions:
𝑅𝑇
𝐸 = 𝐸𝜃 − ln 𝑄
𝑛𝐹
Where Eθ is the electromotive force (EMF) of the cell under standard conditions (STP)
R is the universal gas constant (8.31 J/K∙mol)
T is the temperature in kelvin
n is the number of moles of electrons being transferred in the cell’s balanced equation
F is the Faraday constant (96,500 C/mol)
Q is the reaction quotient:
[𝑖𝑜𝑛𝑠 𝑏𝑒𝑖𝑛𝑔 𝑜𝑥𝑖𝑑𝑖𝑧𝑒𝑑]
𝑄= = 𝐾𝑒𝑞 ← 𝑓𝑜𝑟 𝑒𝑞𝑢𝑖𝑙𝑖𝑏𝑟𝑖𝑢𝑚𝑠
[𝑖𝑜𝑛𝑠 𝑏𝑒𝑖𝑛𝑔 𝑟𝑒𝑑𝑢𝑐𝑒𝑑]
Concentration cell: A cell in which the electrodes in its half-cells are the same, but the
concentration of ions is different. The most common concentration cell is the oxygen
concentration cell, where differences in the amount of dissolved oxygen generate a small
potential difference.
Microbial fuel cell: A fuel cell that converts chemical energy from a substrate into electricity
through anaerobic oxidation performed by a microorganism.
C6H12O6 + 6H2O → 6CO2 + 24H+ + 24e-
Microbial fuel cells can be

extremely compact and could
generate electricity from human
waste, making it an ideal
sustainable energy source and a
possible form of energy for long
space missions.
80
Option C: Energy
C.7 Nuclear fusion and fission (AHL)

Nuclear enrichment: The process of separating U-235 (0.72% of naturally occurring uranium)
from U-238 (99.28% of naturally occurring uranium).
Uranium is found naturally in ore as various uranium oxides. The ore is processed and
purified to uranium (IV) oxide (UO2), also known as uranium dioxide. Since uranium dioxide’s
melting point of 2800°C is too high for separation through gaseous diffusion, it is converted into
uranium hexafluoride, which has a boiling point of 56°C.
UO2 (s) + 4HF (g) → UF4 (s) + 2H2O (g)

UF4 (s) + F2 (g) → UF6 (g)
To separate U-235 from U-238, UF6 is vaporized and

forced through a porous membrane at high pressure.
U-235, being lighter, passes through the membrane
more easily. This process only increases the
concentration of U-235 by a small amount, so it is
repeated several times.
Another method of enrichment uses centrifugation.

Gaseous UF6 is placed in a centrifuge, flowing
opposite to the direction of the centrifuge. The
heavier U-238 remains closer to the wall, while the
enriched UF6 is withdrawn from the centre.
After it is enriched, UF6 is reduced back to uranium

metal for use.
Graham’s law of effusion: The rate of effusion of two gases is inversely proportional to the
square root of their molar masses.
𝑟𝑎𝑡𝑒 𝑜𝑓 𝑒𝑓𝑓𝑢𝑠𝑖𝑜𝑛 𝑜𝑓 𝑔𝑎𝑠 1 𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑔𝑎𝑠 2
=√
𝑟𝑎𝑡𝑒 𝑜𝑓 𝑒𝑓𝑓𝑢𝑠𝑖𝑜𝑛 𝑜𝑓 𝑔𝑎𝑠 2 𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑔𝑎𝑠 1
Decay constant (λ): The first order rate constant for a radioactive decay.
ln 2
𝜆= 𝑁 = 𝑁0 𝑒 −𝜆𝑡
𝑡1/2
Where N0 is the initial amount of a species

N is the amount that remains, NOT the amount that decayed
81
Option C: Energy
Sievert (Sv): The SI unit for ionizing radiation doses. Measures the effect of
ionizing radiation on tissue, in J/kg. Ionizing radiation can remove electrons
from molecules in biological tissue, creating radicals such as superoxide (O2-)
and hydroxyl (HO∙). These radicals can cause chain reactions that damage DNA and enzymes.
Superoxide ions have strong oxidative properties due to its unpaired electron and
oxygen’s tendency to gain electrons. Hydroxyl ions can be created through ionizing radiation or
from superoxide radicals via the Haber-Weiss reaction:
O2- + H2O2 → O2 + OH- + OH∙
C.8 Photovoltaic cells and dye-sensitized solar cells (DSSC)

Conjugation: The interaction of alternating double bonds to produce a delocalized array of pi
electrons. The pi electron clouds of adjacent double bonds overlap to form a large cloud of
delocalized electrons.
In conjugated alkenes, the higher the degree of conjugation, the longer the wavelength
of light that can be absorbed. Remember that the colour of wavelength that is absorbed is
complementary to the colour that is seen.
Silicon semiconductor photovoltaic cells

Semiconductor: A material with an electrical conductivity between conductors and insulators. A
semiconductor’s conductivity increases when heated, while a conductor’s decreases.
Conductors are typically metals with low ionization energies so heating them increases
lattice movement and interferes with conduction. In contrast, semiconductors, with higher
ionization energies and poorer conductivity, increase in conductivity when heated due to the
extra energy allowing electrons to move into a conductor zone.
Photovoltaic cell: A cell that converts light directly into electricity. Semiconductors can absorb
photons, resulting in electrons being knocked off of their atoms, creating a potential difference.
Semiconductors are often made of group 14 materials, such as silicon and germanium. A
semiconductor can be “doped” with small amounts of group 15 or group 13 elements, creating
n-type (“n” – negative) and p-type (“p” – positive) semiconductors respectively.
N-type semiconductors have extra

electrons which can move, given a small
potential difference, while p-type
semiconductors have “holes” which can
“hold” electrons. By placing n-type and p-
type semiconductors together, a one-way
flow of electrons can be achieved.
82
Option C: Energy
Band gap: The difference in energy between the valence and conduction electron energy bands.
The band gap allows for the “on-off” property of semiconductors, which serves as the binary
language in computers.
Dye-sensitized solar cells (DSSC)

Dye-sensitized solar cells (DSSC): A solar cell in which
photons are absorbed by a dye.
In a Grätzel cell, sunlight passes through the

transparent anode to reach titanium (IV) oxide (TiO2)
nanoparticles, covered in dye. Excited electrons are
injected from the dye into the TiO2, which conducts the
electrons to the anode. The dye molecule then regains
an electron from the iodide solution electrolyte, which
oxidizes into triiodide (I3-). The triiodide is then reduced
back to iodide using electrons from the cathode.
The TiO2 nanoparticles form a transparent mesh, which allows electricity conduction.
Different dyes on the TiO2 can be used to absorb different wavelengths of light.
Advantages of dye-sensitized solar cells over Disadvantages of dye-sensitized solar cells

silicon-based solar cells: over silicon-based solar cells:
- Cheaper, use lower energy light - Currently not suitable for large-scale
- Plentiful and renewable resources applications (more than one MWe)
- Surface area due to nanoparticles - Liquid electrolyte can freeze at low
allows for more light absorption temperatures or crack cell at high
- Injection of electron from dye into temperatures, making it unsuitable
mesh reduces chances of electron for extreme weather conditions
“falling back” into “hole”
- Thin-layer structure, making it more
flexible and durable, radiates heat
away better
83

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International Baccalaureate Program

Topic 1: Stoichiometric relationships

Atom economy: A measure of the efficiency of a chemical reaction.

Physical properties: Qualitative and quantitative data.

Physical separation of mixtures

Electrolysis: The application of electricity to a substance to cause a reaction.

HCl → hydrogen chloride → hydrochloric acid

1.2 The mole concept

Isotopes: Variants of a particular chemical element that differ by neutron number.

Empirical formula: The lowest whole number ratio of elements in a compound.

1.3 Reacting masses and volumes

Theoretical yield: The expected amount of product produced in perfect conditions.

Percent purity: The purity of a sample.

Gasses and gas laws

Charles’ law: A gas’ volume is directly proportional to its absolute temperature. 𝑉 ∝ 𝑇

Gay-Lussac’s law: A gas’ pressure is directly proportional to its absolute temperature. 𝑃 ∝ 𝑇

1. Formula equation: The complete chemical equation.

2. Complete/Total ionic equation: Shows dissociated ions.

Topic 2 & 12: Atomic structure

1897: J.J. Thomson discovers the negative charge of the

1909: Robert Millikan determines the mass of the

1932: James Chadwick discovers the

Carbon-14 is present in the atmosphere at a constant level through the bombardment of

The process of mass spectrometry has five stages:

2.2 Electron configuration

Wavelength (λ): The length of one complete wave, in metres or nanometres.

Principal quantum number (n): The energy

Ionization energy: The amount of energy

RH is the Rydberg constant for hydrogen, roughly 1.097 × 107/m.

Orbitals and electron configurations

S-orbital: Spherical shells around the

Inner shell orbitals: d- and f-

Aufbau principle: Electrons fill orbitals

12.1 Electrons in atoms

1 s t ionization energy trends across a period

Ionization energy and electron configuration

Ionization energy increases as

The large increases in ionization

Topic 3 & 13: Periodicity and the

IUPAC recommended group names:

3.2 Periodic trends

Electronegativity trends are the same as those in ionization energy. Electronegativity

Trends of oxides across a period

Oxide reactions to memorize:

Al2O3 is amphoteric, meaning it can react both as an acid and as a base:

Halogen compound Colour State at room temperature

I2 (s) + 2Cl- (aq) → no reaction Br2 (aq) + 2KCl (aq) → no reaction

13.1 First-row d-block elements

The elements of the d-block are classified into three types:

Type A Type B Type C

The range of oxidation states for

+2 is the common charge of d-

Complexes of transition metals

Ligand: A species that provides electrons for a coordinate bond.

Coordination number: The actual number of ligands in a complex ion.

Pauling electronegativity: An approximate method of estimating the

[Fe(H2O)6]3+ Fe has a charge of 0.

Different ligands can replace one another in their concentrations change:

[Cu(H2O)6]2+ + NH3 → [Cu(NH3)6]2+ [Cu(NH3)6]2+ + Cl- → [Cu(Cl)4]2-

[Pt(NH3)4Cl2] + Ag+ (aq) → no reaction

Ethylenediamine: Also called 1,2-ethanediamine (H2NCH2CH2NH2), a bidentate ligand.

Oxalate: Also called ethanedioate, (C2O4)2-, a bidentate, dianionic ligand. Abbreviated to

Ethylenediaminetetraacetate: (EDTA)4-, a polydentate ligand capable of forming up to

Transition metals as catalysts