GRADE12CHEMISTRY

OLYMPIADSCHOOL

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Reviewof1st halfofGrade12Chemistry

OrganicChemistry Organic Chemistry

 Organic chemistry is the study of compounds that are based on CARBON. C b atoms can form strong single, Carbon t f t i l double, or triple bonds with other carbon atoms. Th three-dimensional shape of a molecule i The th di i l h f l l is particularly important when the molecule contains polar covalent bonds. A polar covalent bond is a covalent bond between two atoms with different electronegativities. Electronegativity is a measure of how strongly an atom attracts electrons in a chemical bond. The electrons in a polar covalent bond are attracted more strongly to the atom with the higher electronegativity. This atom has a partial negative charge, charge while the other atom has a partial positive charge. Thus, every polar bond has a bond p p g g partial dipole: a partial negative charge and a p positive charge, separated by the length of the f bond.

 The figure illustrates the polarity of a double carbon-oxygen bond. Oxygen has a higher yg yg g electronegativity than carbon. Therefore, the oxygen atom in a carbon-oxygen bond has a partial negative charge, and the carbon atom has a partial positive charge.

To determine molecular polarity, you must consider the shape of the molecule and the bond dipoles within th molecule. ithi the l l If equal bond dipoles act in opposite directions in three-dimensional space, th counteract each th di i l they t t h other. A molecule with identical polar bonds that point in opposite directions is not polar polar.

Hydrocarbons
Hydrocarbons are the simplest type of g p y p organic compound. They are composed entirely of carbon and hydrogen atoms, and are widely used as fuels Because fuels. they contain only carbon and hydrogen atoms, atoms hydrocarbons are non polar non-polar compounds.

 An alkane is a hydrocarbon that has only single bonds. Alkanes that do not contain rings have the formula CnH2n + 2. An alkane i the shape of a ring i called a cycloalkane. lk in h h f i is ll d l lk Cycloalkanes have the formula CnH2n. A alkene i a compound th t has at least one d bl b d An lk is d that h tl t double bond. Straight-chain alkenes with one double bond have the same formula as cycloalkanes CnH2n cycloalkanes, CnH2n. * A double bond involves two pairs of electrons. In a double bond, one pair of electrons forms a single bond and the other , p g pair forms an additional, weaker bond. The electrons in the additional, weaker bond react faster than the electrons in the single bond. Thus, carbon-carbon double bonds are more reactive than carbon-carbon single bonds. A alkyne i a compound th t h at l An lk is d that has t least one t i l b d A t triple bond. straight chain alkyne with one triple bond has the formula CnH2n - 2 Triple bonds are even more reactive than double 2. bonds. The functional group for an alkyne is the triple bond.

 A functional group is a reactive group of bonded atoms that appears in all the members of a chemical f il E h f f h i l family. Each functional group ti l reacts in a characteristic way. Thus, functional groups help to determine the physical and chemical properties of compounds. The general formula for a family of simple organic compounds is R + functional group. The letter R stands for any alkyl group. (If group more than one alkyl group is present, R2 and R3 are also used.) used ) 1. 1 Compounds with the same functional group often have similar physical properties. 2. 2 Compounds with the same functional group react chemically in very similar ways.

 Alcohols, alkyl halides, ethers, and amines all g p g have functional groups with single bonds. An alcohol is an organic compound that contains the OH functional group Depending group. on the position of the hydroxyl group, an alcohol can be primary, secondary, or tertiary.

 An alkyl halide (also known as a haloalkane) is an alkane in which one or more hydrogen atoms have been replaced with halogen atoms such as F Cl Br or I The atoms, F, Cl, Br, I. functional group of alkyl halides is RX, where X represents a halogen atom. Alkyl halides are similar in structure, polarity, and reactivity t alcohols. t t l it d ti it to l h l An ether is an organic compound that has two alkyl groups joined by an oxygen atom The general formula atom. of an ether is ROR. You can think of alcohols and ethers as derivatives of the water molecule. Aldehydes and ketones both have the carbonyl functional group. An aldehyde is an organic compound that has a double bonded oxygen on the last carbon of a double-bonded carbon chain. The general formula is RCOH. A ketone is an organic compound that has a double-bonded oxygen on any carbon within the carbon chain. The general formula for a ketone is RCOR2, where R and R2 are alkyl groups groups.

 A carboxylic acid is an organic compound with the carboxyl group. group The general formula for a carboxylic acid is RCOOH RCOOH. An ester is an organic compound that has the general formula RCOOR2, where R is a hydrogen atom or a hydrocarbon, hydrocarbon and R2 is a hydrocarbon You can think of an hydrocarbon. ester as the product of a reaction between a carboxylic acid and an alcohol. __________________________________ ** B Benzene i a cyclic compound with th equivalent of three is li d ith the i l t f th double bonds and three single bonds However, the electrons that form the double bonds in benzene are spread out and p shared over the whole molecule. Thus, benzene actually has six identical bonds, each one half-way between a single and a double bond. These bonds are much more stable than ordinary double bonds and do not react in the same way. Molecules with this type of special electron sharing are called aromatic compounds compounds.

Reactions of Organic Compounds

There are 3 main types of Organic Reactions: Addition reactions; S b tit ti reactions; and Substitution ti d Elimination reactions at o eact o s * Most organic reactions can be classified as one of these three t pes types.

 In an addition reaction, atoms are added to a p p double or triple bond. One bond of the multiple bond breaks so that two new bonds can form. g , To recognize an addition reaction, remember that two compounds usually react to form one major product. (Sometimes two isomers are formed.) The product has more atoms bonded to carbon atoms than the organic reactant did. Addition reactions are common for alkenes and alkynes. alkynes Addition reactions can also occur at a CO bond.

 In a substitution reaction, a hydrogen atom or a g p p y functional group is replaced by a different functional group. Two compounds usually react p g to form two different products. The organic reactant(s) and the organic product(s) have the same number of atoms bonded to carbon. Alcohols, alkyl halides, and aromatic compounds commonly undergo substitution reactions.

 In an elimination reaction, atoms are removed from a molecule to form a double bond. This type of reaction is the re erse of an addition reaction One reverse reaction. reactant usually breaks up to give two products. The organic product typically has fewer atoms bonded to carbon atoms than the organic reactant did. Alcohols often undergo elimination reactions when they are heated in the presence of strong acids, such as sulfuric acid, H2SO4, which acts as a catalyst. Alkyl halides also undergo elimination reactions to produce alkenes alkenes.

 REDOX: Oxidation and reduction always occur together. One reactant is oxidized while the other reactant is g y, reduced. In organic chemistry, oxidation and reduction are defined by the changes of the bonds to carbon atoms in the organic reactant. Oxidation is defined as a reaction in which a carbon atom forms more bonds to oxygen, O, or less bonds to hydrogen, H. Oxidation occurs when an organic compound reacts with an oxidizing agent Common agent. oxidizing agents include acidified potassium permanganate, KMnO4, acidified potassium dichromate, K2Cr2O7, K2Cr2O7 and ozone O3. The symbol [O] is used to ozone, O3 symbolize an oxidizing agent. Reduction is defined as a reaction in which a carbon atom forms fewer bonds to oxygen O or more bonds to oxygen, O, hydrogen, H. Often, a CO bond or CC bond is reduced to a single bond by reduction. Reduction occurs when an organic compo nd reacts with a red cing agent compound ith reducing agent. Common reducing agents are lithium aluminum hydride, LiAlH4, and hydrogen gas over a platinum catalyst, H2/Pt. Th H2/Pt The symbol [H] is used t symbolize a reducing b l i d to b li d i agent.

Atoms,ElectronsandPeriodicTrends
Rutherford: the atom is made up mainly of empty space, with a small, massive region of py p , , g concentrated charge at the centre. the nuclear model of the atom The problem: Atomic Spectra - The visible p portion of the electromagnetic spectrum is a g p continuous spectrum. According to nineteenth century physics, part of the energy emitted by y y gy y electrons should be observable as a continuous spectrum. This is not the case. Instead, when atoms absorb energy, you observe a pattern of t b b b tt f discrete (distinct), coloured lines separated by spaces of varying length length.

 Bohr was able to explain the line spectrum for hydrogen because his idea incorporated several y g p new id ideas about energy. b t Bohrs model: Pictures electrons in orbit around a central nucleus. U lik R th f d model, i t l l Unlike Rutherfords d l in which electrons may move anywhere within the volume of space around the nucleus Bohrs model nucleus, Bohr s imposes restrictions.

 Planck suggested that matter, at the atomic level, can absorb or emit only discrete quantities of energy. Each of these specific quantities is called a quantum of energy. Planck said that the energy of energy an atom is quantized. Einstein said that light was also quantized It quantized. occurs as quanta of electromagnetic energy that have particle like properties. These particle like particle-like properties particle-like packets of energy were later called photons. In Einstein s view, Einsteins view light (and all electromagnetic energy) travels in the form of photons of energy. The energy that is associated with the coloured lines in this spectrum corresponds to the change in energy of an electron as it moves to higher or lower energy levels.

When a hydrogen atom is exposed to electrical current, or to another form of electromagnetic energy, its electron absorbs photons of energy. It is now in an excited state. When an electron of a hydrogen atom absorbs energy it is excited to a energy, higher energy level. When the electron falls to a lower energy level, it emits light of certain energy. A line spectrum results when atoms in an excited state emit photons as they fall to lower energy l f ll t a l level. Thi i an emission spectrum. l This is i i t

 Another kind of spectrum that is related to an atoms emission spectrum is an absorption spectrum. This kind of spectrum p p p p results when electrons of atoms absorb photons of certain wavelengths, and so are excited from lower energy levels to higher energy levels. levels

 Schrdinger introduced the concept of quantum mechanics - a branch of physics that uses mathematical equations to describe the wave properties of submicroscopic particles such as electrons, atoms, and molecules. Schrdinger used concepts from quantum mechanics to propose a new atomic model. The quantum mechanical model of the atom: This model describes atoms as having certain allowed quantities of energy because of the wave-like properties of their electrons. The figure depicts the volume surrounding the nucleus of the atom as being indistinct or cloud like cloud-like because of a scientific principle called the uncertainty principle.

 HeisenbergUncertaintyPrinciple:If you can know an electrons precise p p position and p path around the nucleus, as you would by defining its orbit, you cannot know with certainty its velocity. Similarly, if you know its precise velocity, you cannot know with certainty its position. Based on the uncertainty principle, B h atomic model i fl i i l Bohrs t i d l is flawed b d because you cannot assign fixed paths (orbits) to the motion of electrons. f l t Schrdinger used a type of equation called a wave equation to define the probability of finding an atoms electrons at a particular point within the atom. There are many solutions t this wave t Th l ti to thi equation, and each solution represents a particular wave f function. ti

 Each wave function gives information about an electron s electrons energy and location within an atom atom. Chemists call these wave functions ORBITALS. O bi l h Orbitals have a variety of diff i f different possible ibl shapes. Therefore, scientists use four quantum numbers to describe an atomic orbital. One quantum number, n, describes an orbitals orbital s energy level and size. A second quantum number, l, number l describes an orbitals shape. A third orbital s shape quantum number, ml, describes an orbitals orientation i space. A f th quantum number, i t ti in fourth t b the spin quantum number, ms, describes the spin of an electron.

 PaulisExclusionPrinciple:Only two electrons of opposite spin can occupy an orbital OR No two electrons in an atom have the same four quantum numbers OR E h electron in an h f b Each l i atom has its own unique set of four quantum numbers.

MorefromAtoms,Electronsand PeriodicTrends
HistoricalEvents,OrbitalFilling;Trendsinthe p PeriodicTable;thes,p,dandfblocks;etc...

Structures and Properties of Substances (Chemical Bonding) Chemical bonds are electrostatic forces that hold atoms together in compounds. Why do atoms form bonds at all? The answer involves energy. Lower-energy systems tend to have greater stability than higher-energy higher energy systems. Bonded atoms, therefore, tend to have lower energy than single uncombined single, atoms. Chemical bonding involves the interaction of valence electrons

 Ionic Bonding: The force of attraction between pp y g , { } oppositely charged ions, cations {+} and anions {-}, constitute an ionic bond. Ionic bonding occurs between atoms of elements that have large differences in electronegativity usually a metal with a low electronegativity and a nonnon metal with high electronegativity. general, In general ionic solids have the following properties: Crystalline with smooth shiny surfaces smooth, Hard but brittle Non-conductors of electricity and h t N d t f l t i it d heat High melting points Many ionic solids are also soluble in water.

 CovalentBonding:Covalentbondsareforcesofattractionformed whenatomsofamoleculeshareelectrons. Covalentbondinginvolves when atoms of a molecule share electrons. Covalent bonding involves abalancebetweentheforcesofattraction andrepulsionthatact betweenthenucleiandelectronsoftwoor moreatoms. Thequantummechanicalmodelcanbeextendedtoexplainbonding. A covalentbondmayformwhentwohalffilledatomicorbitals from two atoms overlap to share the same region of space A covalent atomsoverlaptosharethesameregionofspace.Acovalent bondinvolves theformationofaneworbital,causedbythe overlappingofatomic orbitals.Theneworbitalhasenergylevelsthat arelowerthanthoseof theoriginalatomicorbitals.

 Bond energy (E) is a measure of bond g strength in a chemical bond. It is the heat required to break Avogadro's number of molecules into their individual atoms. Bond energy is the energy required to break the force of attraction between two atoms in a bond and to separate them. Thus, bond energy is a measure of the strength of a bond. To predict an ionic versus covalent bond, consider electronegativity: A high electronegativity difference is characteristic of ionic compounds. It is common for chemists to compounds describe the formation of ionic compounds in terms of a transferring of electrons from one atom to another.

 Chemists consider bonded atoms with a difference in EN between 0 and 0 4 as being 0.4 mostly covalent; electrons are shared equally or nearly equally. equally For bonded atoms that have a difference in EN between 0.4 and 1 7 the bond is termed 1.7, polar covalent. A polar covalent bond is a covalent bond with an unequally shared pair of electrons between two atoms. This unequal sharing results in a bond that has partially positive and partially negative poles. Bonded atoms with a difference in EN between 1.7 and 3.3 are mostly ionic; electrons are shared so unequally that one bonded atom has a strong negative t h t ti charge and the other has a strong positive charge.

MorefromStructuresandProperties More from Structures and Properties ofSubstances(ChemicalBonding) ( g)

Lewis Structures Coordinate Covalent LewisStructures,CoordinateCovalent Bonding,ResonanceStructures,VSEPR, MolecularGeometry,IntermolecularForces, Molecular Geometry Intermolecular Forces etc...

Energy and Change (Studying Energy Changes)

Th l The law of conservation of energy states that the f ti f t t th t th total energy of the universe is constant. In other words, words energy can be neither destroyed nor created. This idea can be expressed by the following equation: Euniverse = 0 g q
Universe = System + Surroundings
Euniverse = Esystem + Esurroundings = 0 Esystem = Esurroundings Esurroundings

Heat, Q, refers to the transfer of kinetic energy. Heat is expressed in joules (J). Temperature, T, is a measure of the average kinetic energy of the particles that make up a substance or system. * Temperature in Kelvin degrees = Temperature in Celsius degrees + 273.15

 Chemists define the total internal energy of a substance at a b t t constant pressure as its enthalpy, H. Chemists study the enthalpy change, H, that accompanies a process the relative enthalpy of the reactants and products in a system. In chemical reactions, enthalpy changes result from chemical bonds being broken and formed. Chemical bonds are sources of stored energy. Breaking a bond is a process that requires energy. C ti a Creating bond is a process that releases energy.

MorefromEnergyandChange (StudyingEnergyChanges)
HeatCapacity,SpecificHeatCapacity (Q mcT), Calorimeters, Hess Law of Heat (Q =mcT),Calorimeters,Hess LawofHeat Summation,CalculatingEnthalpyChanges

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