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H2 C HEMISTRY
CONTENTS PERIODICITY ORGANIC CHEMISTRY MECHANISMS BIOCHEMISTRY SUMMARY PHYSICAL & CHEMICAL PROPERTIES HALOGENS CHEAT SHEET DEFINITIONS THINGS TO NOTE
Notes by Zhuoyi. Released under Creative Commons Remix License. evin. Distributed on Erpz.net. Consolidated & Updated by
PAGES 2 6 8 10 13 14 16
1
CHEMICAL PERIODICITY
PHYSICAL PROP ERTIES
Property Atomic radii decrease across a period
Zeff = Z
Atomic radii increase descending a the size of From Na to Al, The Zeff increases from Na to Al as the cation has one less shell of the electrons, Consequently, the nucleus exerts a greater attractive force on cation is always smaller the valence electrons in the cation. than P to Cl, the size From Both the anion and its parent atom have the same number of protons, of the anion is always making Z identical. The anion however, has more electrons that its larger than the parent parent atom, making the nucleus attract the valence electron less atom t ro ly in Size of isoelectronic ions s rn eg mai nsthe c oanion nsta nt as the have the same number of inner electrons. decrease across a period Z increases, and thus the nucleu s attra cts the val ence ele ctron sm ore strong ly For more information about ionization energy, refer to the atomic structure cheatsheet st 1 IE decreases Zeff decreases descending a group. Z increases descending a group while i nc rease s as well, but more significantly descending a group Electrons are removed from an ions with increasing positive charges, nd st 2 IE > 1 IE always increasing the Zeff Electronegativity Zeff increases across a period. Z increases while remains approximately constant. The ability of an atom in a molecule to increases attract electrons thus increases. across a period Electronegativity Zeff decbonding reases across a period. While Z increases, increases more significantly. Thus, the ability of an atom in a molecule to attract decreases bonding electrons decreases. Period 2 Period 3 Typ e Structure Bonding mp/bp Electrica l conductivi Li Na Be Mg Al Metal Metalli Strong c metallic bonds Depends on no.
of valence e Na < Mg < Al Hig
-
Explanation Zeff increases across a period. The number of protons, and thus Z, increases, while remains approximately constant as the number of fully filled inner principle quantum shells remain the same Zeff decreases descending a group. The number of protons, and thus Z, increases, while
C* Si Metalloi Giant d Molecular Strong covalent bonds Very High Poor conductors
*Graphite is a slightly
N P
h Good conductors
Depends on no. of
Insulator s
No mobile
CHEMICAL PROPERTIES
Reaction with dry oxygen and heat Na 4Na + O2 2Na2O Vigorous Reaction with dry chlorine and heat 2Na + Cl2 2NaCl Very vigorous Mg + Cl2 MgCl2 Vigorou s 2Al + 3Cl2 3AlCl3 Vigorou s Si + 2Cl2 SiCl4 Slow P4 + 6Cl2 4PCl3 PCl3 + Cl2 PCl5 S8 + 4Cl2 4S2Cl2 S2Cl2 + Cl2 2SCl2 Reaction with water pH in wate 13
Gp I
Strongly reducing
Gp II
2Na + 2H2O 2NaOH + H2 Violent reaction with cold water Mg + H2O MgO + H2 Vigorous reaction with steam 2Al + 3H2O Al2O3 + 3H2 Vigorous reaction with steam No reaction
Mg
Gp III
Al
Si
Si + O2 SiO2 Slow P4 + 3O2 P4O6 P4O6 + 2O2 P4O10 S + O2 SO2 2SO2 + O2 2SO3 2Cl2 + 7O2 2Cl2O7 Slow
No reaction
No reaction
Cl
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H2 Chemistry | Consolidated Notes
Na2 O + 1
MgO + 2
Al2O + 3
-
SiO2 +
10
P4O6 P O +3, 5
No. of valence e Bondin Structure State at 20C Molten electrical conductivi Solubility in
Multiple oxidation numbers. Atoms have unoccupied, lowlying 3d orbitals that can be used to expand
Solubl 12
Strongly
High bp due to large amount of energy required to break ionic bonds in the lattice (Na, Mg, Al) or giant covalent Good Very Mobile ions present in molten poor state No charged
Sparingly 9
Weakly
Insolubl e
conductivity No mobile instrongly liquid React with water to ions form acidic 2
Strongly
pH of solution
2 Na O(s) + 2 H MgO(s) + H O(l) O(l) Mg(OH)2(a 2NaOH(a q) q) Basic ; Hydroxides are strongly
Lattice energy highly Please dont memorize these equations. Remember: oxidation states dont 2 change on either side. Write the reactants product, and then balance all non-O and non-H elements and finally balance with water.
Cl2O(g) + H2O(l) 2HClO(a q) Cl2O7(l) + H2O(l) Acidic 2NaClO(aq) H2O(l) Cl + O(g) + 2NaOH(aq)
MgO(s) + 2HCl(aq)
Mg(OH)2(aq) + 2HNO3(aq)
2MgCl2(aq) + H2O(l)
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SiO2(s) + 2NaOH(aq)
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H2 Chemistry | Consolidated Notes
CHLORIDES + PRO P E R T I ES
Oxid e
Oxidation number Structure State at 20C Molten electrical conductivit Solubility in water pH
NaC l + 1
MgCl + 2
2
AlCl
3
SiCl
4
SCl
2 2 2
Simple molecular
Comparable e-
+1, +2
Liquid, gas
Dissolv
6.5
Slightly acidic
3
Strongly acidic
2+
Equations
Notes by Zhuoyi. Released under Creative Commons Remix License. Consolidated & Updated by Kevin. Distributed on
+ 2Cl (aq)
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H2 Chemistry | Consolidated Notes
E L E C T R O P H I L I C A D D I T I ON
Exemplified by the addition of HBr to an alkene
Step 1
+ H
Br
slow
C H
C +
Br
carbocation intermediate
Step 2
C H
C +
:Br
fast
C C H Br
H
Electrophi lic attac k
NO 2 +
Step 2
NO 2
slow
benzonium ion
H
Step 3
Loss of proton
NO 2 + fast
NO 2
HSO4
H2SO4
NUCLEOPHILIC SUBSTITUTION S
R3 R3 X Nu R1 C X R2
2 ONE STEP
R3 Nu C R2 R1
6
Nu :
R1
+ C R2
+ X
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pentavalent transition state
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NUCLEOPHILIC SUBSTITUTION S
R3 X C + R1 R2 slow Nu :
-
1 TWO STEP
R3 R3
R3 C
+
fast
-
Nu
C R2 R 1
Nu
R 1 R2
: Nu
R 1 R2
NUCLEOPHILIC ADDITION
Exemplified by the addition of CN to ethanal Step 1
Generation of
-
KCN
K + CN
Step 2
Nucleophili c attac k
H3C + C H
CN
:CN
slow
H3 C
C H
Step 3
Protonatio n
OH
CN
BIOCHEMISTRY
AMINO ACIDS
Amino acids are zwitterionic forms strong ionic bonds at isoelectric point (pI)
Solubilities of amino acids are at a minimum at pI. Lattice energy is most exothermic at this point as the zwitterions experience the greatest ionic attraction Zwitterions have high melting points due to strong ionic bonds
Negatively chargedacid Aspartic (-CH2COOH) Positively charged Uncharged Lysine (-(CH2)4NH2) Serine (CH2OH) Cysteine (-
Classification of amino acids Type Nonpolar Example Glycine (-H) (R group) Alanine (-CH3) Reactions of amino acids Two important reactions to remember Salt formation + + + H3N -R-COO H3N -CHR+H COOH + H3N -R-COO -+ OH - H2N-CHRCOO + H2O Hydrolysis of peptides Acidic hydrolysis -R-CONH-R- + -R-COOH + H 3N
H , heat
+
Peptide bond formation H3N -R-COO + H3N -R-COO H3N -R-CONH-R -COO + H2O
+ + + -
peptide bond
Basic hydrolysis
Enzymatic hydrolysis O H- , heat May be catalyzed by R-CONH-R enzymes like -R-COO + H Ntrypsin, pepsin etc. R-
PROTEINS
The primary structure of a protein refers to the number and sequence of amino acids in a polypeptide chain. E.g.: ala-gly-leu-tyr-his-ala-leu-phe The secondary structure of a protein refers to the local spatial conformation of the polypeptide backbone, in the form of either -helices or -pleated sheets. -helix -pleated sheet Right-hand screw Stabilized by hydrogen-bonds between CO and NH group in each peptide link is NH groups in adjacent strands hydrogen-bonded May be antiparallel or parallel to the CO group of the fourth following Side chains on successive AA residues appear on peptide link opposite sides of the sheet 3.6 AAs per turn The tertiary structure of a protein refers to its three-dimensional structure of the polypeptide. 1. Hydrogen bonding a. Between polar side chains (-OH, -NH, =O, =NR groups) 2. van der Waals forces a. Electrostatic interactions among permanent or induced dipoles b. Hydrophobic interactions contributed by nonpolar side chains which cluster away from water to avoid destabilisation of side chains (a hydrophobic core is formed) 3. Ionic interactions a. Between two oppositely charged side chains (e.g. Asp and Lys) usually groups that ionize in water 4. Disulphide bridges a. Between cysteine residues with the thiol (SH) side chain b. R-SH + HS-R + *O+ R-S-S-R + H2 O The quaternary structure of protein refers to the spatial arrangements and association of the polypeptide subunits of proteins.
DENATURATION OF PROTEINS
Denaturation refers to the disruption in the secondary, tertiary and quaternary structure of proteins by the breaking of the non-covalent (but including disulphide bridges) interactions that hold these structures in their native conformation. Effect Effect Effect of Temperature Heating causes an increase in the thermal vibration of the molecule Hydrogen bonding is disrupted Proteins denature and thus unfold of pH If pH is lowered far below pI, the protein will only contain positive charges Like charges repel each other and cause the denaturation of proteins Likewise for high pH of Heavy Metal Ions 2+ 2+ Heavy metal ions (Pb , Cd , etc) are positively charged Compete with positively charged groups for attraction with negatively charged groups 2+ Also bond with SH groups (especially Hg ) and disrupt disulphide bridges Resident metal ions in certain proteins may also be displaced
E N Z Y M ES
Enzymes are biological catalysts they increase the rate of reaction without themselves being changed at the en d of the reaction. They catalyze reactions by providing an alternate route of reaction with lower activation energies. Characteristics Specificity: only certain substrates are acted upon by enzymes, and only a single type of reaction takes place Large catalytic power: some enzymes can speed up reactions by a billion times
ALKANES
Property Explanation Non-polar Difference in electronegativities of C and H atoms are negligible (id-id interactions) bp/mp increases with A larger electron cloud is more easily polarized and id-id interactions molecular size become greater, and since boilingis involves the of IMF, area bp and mp increases bp/mp decreases with A branched omer has a breaking smaller surface and hence a lowwith er extent of branching IMF between its Insoluble in polar solven ts, soluble in non-polar solvents molecules Density increases with molecular size; less dense than water Unreactive Non-polar and saturated and do not contain any region of high e density
ALKENES
Property Similar to alkanes cis- isomers have higher bps than transisomers cis- isomers have lower mps than transisomers Explanation The cis- isomer is polar and has pd-pd as well as id-id interactions, while the trans- isomer has only id-id interactions trans- isomers pack better into a crystal lattice and have higher mps than cis- isomers
HALOGEN DERIVATIVES
Property Less reactive than benzene (in ES) less reactive to Ar-X SN as compared to R-X Higher bp/mp than corresponding alkane Explanation Highly electronegative halogen deactivates the ring Partial double bond character in the arene C-X bond due to p-orbital overlap with the -cloud The of the e riand ch rin g hinder nucleophilic attack The presence alkane is non-polar has only id-id interactions, where R-X has a polar bond and hence pd-pd interactions. Also, the number of e is larger, increasing id-id interactions.
HYDROXY COMPOUNDS
Acidity: The stability of the acid anion determines the acidity of a compound Ethanol < Water < Neither destabilizing or The phenoxide ion is alkoxide ion Phenol is destabilized by the positive inductive stabilizing effects are stabilized by the present delocalization of the negative effect of the e donating a l kyl g r o u p s charge Effects of substituents Ethanol Phenol e releasing groups on the hydroxyl carbon e releasing groups decreases the acidity of decreases acidity phenol as it as it intensifies the negative charge on reduces the delocalization of the negative the oxygen, charge on the destabilizing the anion
CARBONYL COMPOUNDS
Property Higher bp than corr alkane, lower bp than corr alcohol Solubility in water decreases as number of C increases; soluble in organic
Explanation pd-pd interactions as compared the id-id interactions in alkanes lack of h-bonding when comparing with alcohols Unable to form h-bonding with water. Higher carbonyl compounds have larger hydrophobic groups.
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H2 Chemistry | Consolidated Notes
RCOCl Highly polarized alpha-carbon as it is bonded to two highly electronegative atoms sp hybridized C experiences less steric
2
> Less polarized alpha-carbon as it is only bonded to one electronegative atom sp hybridized C experiences more
3
RCl > Electron-rich benzene ring repels nucleophile Partial-double bond character makes
NITROGEN DERIVATIVES
Property Higher bp than corr alkanes, lower bp than corr alcohols bp increases with molecular size members are highly Lower soluble in water (max 5C in amines) Amides are polar Tertiary amides have low bp Amides are neutral Explanation O-H h-bond is stronger than N-H h-bond as O is more electronegative Increase in size of electron cloud increases polarizability resulting in greater IMF h -bondin g with water formed easily for both amines and amides; solubility decreases in higher members due to greater hydrophobic nature (also, phenylamine) The highly electronegative N is bonded to H, forming h-bonding They do not form h-bonding with each other due to the absence of a N-H bond, however with water and hydroxylic The lone the pairform on N h-bonding id delocaliz ed over the O-C-N moietysolvents
Basicity of amines: The ability to donate the lone pair on N determines basicity ArNH2 < RRRNH < NH3 < Tertiary amines have Electron releasing R groups increase basicity The lone pair on relatively low basicity as they increase the electron density of the N is delocalized due to steric hindrance lone pair on N, making it so very big more into the from three bulky R available to accept a proton -cloud, groups making it less avai la b lesubstituents for dative on ArNH2: Kb decreases Effect of with e withdrawing substitutents, and vice versa
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H2 Chemistry | Consolidated Notes
HALOGENS
Down group VII Explanation Boiling involves the overcoming of id-id interactions between the halogen Volatility molecules. The size of the decreases electron cloud increases descending the group, and thus becomes more Atomic and ionic polarizable. Hence, boiling point increases. Effective nuclear charge decreases. Both nuclear charge and shielding radii increase Electronegativity increase, but the latter to a more significant extent. decreases Oxidising power From standard electrode potential values decreases Atomic size increases due to decreasing effective nuclear charge. The orbitals are less diffuse, and the orbital overlap is consequently less effective. BDE decreases For F2: There is great electrostatic repulsion between the lone pairs on the F EXCEPT for F2 atoms in F2, leading to a less effective orbital overlap between the bonding orbitals.
REACTIONS
F2 oxidizes water Cl2 oxidizes water 2F2(g) + 2H2O 4HF(aq) + O2(g) Cl2(g) + 2H2O 2HOCl(aq) + HCl(g) 2HOCl 2HCl(aq) + O2(g)
Halogens disproportionate in cold, X2 (g) + 2OH (aq) X (aq) + XO (aq) + H O(l) 2 aqueous alkalis to give h al i d e and h alate (I) i o n s Halogens disproportionate in hot, aqueous X2 (g) + 6OH (aq) 5X (aq) + XO (aq) + H O(l) 3 2 alkalis to give hal ide and halate (V) ioto ns form Halogens react with hydrogen hydrogen X2(g) + H2(g) 2HX(g) halides
The vigour of reaction is dependent on the
HYDROGEN HALIDES
Down group VII Explanation Thermal stability Down Group VII, the valence orbitals become more diffuse, resulting in less decreases effective orbital overlapdepends , hence aon we ake r H-Xstrength. bond is formed, Acidity HX bond Since H-X bond strength decreases down Acidity of the group, acidity increases
REACTIONS
HBr and HI are oxidised when heated with concentrated H2SO4
The reactions differ as I is a stronge reducing agent
-
2HBr(g) + H2SO4(l) Br2(g) + SO2(g) + 2H2O(l) 8HI(g) + H2SO4(l) 4I2(g) + H2S(g) + 4H2O(l)
METAL HALIDES
Colour AgCl AgBr AgI White Cream Yellow Excess NH3(aq) Soluble* Insoluble* Insoluble* conc NH3(aq) Soluble Soluble Insoluble Effect of sunlight Turns grey Turns yellow No visible change Why AgCl is soluble in NH3(aq) but not AgBr/AgI: The Ksp values of AgBr/AgI are extremely low. Even + when [Ag ] is lowered when NH3 is added, the IP still exceeds Ksp such that AgBr/AgI remain insoluble.
REACTIONS
Heating MX in concentrated H2SO4 produce their hydrogen halides.
HBr and HI are further oxidised. See above.
NaX(s) + H2SO4(l) NaHSO4(s) + HX(g) NaX(s) + H3PO4(l) NaH2PO4(s) + HX(g) P4(s) + 6X2 4PX3 PX3 + 3H2O(l) 3HX(g) + H3PO3(aq)
HX can be prepared in situ by reacting MX with concentrated H3PO4 HX can be prepared in situ by reacting X2 with red phosphorus
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H2 Chemistry | Consolidated Notes
DEFINITIONS
O R GA NI C C HE MI ST R Y Enantiom ers Stereoisomers which rotate planepolarized light in opposite directions Racemic mixture A mixture of equal proportions of enantiomers where there is no net optical activity Meso compound An optically inactive compound with plane of symmetry and more than one chiral center. Electrop hile Electron-deficient species Nucleop hile Electron-rich species E N E R G E T I C S Hess Law states that the enthalpy change of a reaction is determined by the initial and final state of the system and is independent of the pathway taken. Standard enthalpy change of r reaction - H The heat change when molar quantities of reactants as specified by the chemical equation react to form products at standard conditions Standard enthalpy change off formation - H The heat change when 1 mole of a pure compound in a specified state is formed from its constituent elements in their standard states at standard conditions. H2(g) + O2(g) H2O(l) H
= Hf [H2O(l r
change takes place on adding more solvent (infinite dilution) at standard 2 conditions. (aq) CuSO4(s) (aq) + Cu SO4 = H soln [CuSO4(s)] H Standard enthalpy change of hyd hydration - H The heat energy evolved when 1 mole of the gaseous ion is dissolved in a large amount of water at standard conditions + + Na (g) Na (aq) a H H
r = hy d r 2-
[Na]
Bond energy - BE The average energy absorbed when 1 mole of X-Y bonds are broken in gaseous state CH4(g) C(g) + 4H(g) = H r 4BE [CH] Bond dissociation energy - BDE The energy required to break 1 mole of that particular XY bond in a particular compound in gaseous state. CH4(g) CH3(g) + H(g) = H r BDE [CH] First ionization energy - 1 IE
st
The energy required to remove 1 mole of electrons from 1 mole of gaseous atoms in the ground state to form 1 mole of gaseous unipositive charged cations. + Na(g) Na (g) + e = st H r 1 IE [Na] Second ionization energy - 2 IE The energy required to remove 1 mole of electrons from
nd
)]
1 mole of ions to form 1 mole of gaseous X + gaseous X charged cations. + 2+ Na (g) Na (g) + e H r = IE [Na] 2 CO2(g)
nd
2+
Standard enthalpy change of c combustion - H The heat evolved when 1 mole of a substance is completely burned in oxygen at standard conditions. C(s) + O2(g)
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First electron affinity 1 EA H
= H [C(s) r c st
H2 Chemistry | Consolidated Notes The energy change when 1 mole of electrons are added ] to 1 mole of atoms in the gaseous state to form 1 mole of gaseous X ions Cl(g) + e Cl (g) H = EA [Cl] st 1
nd r -
Standard enthalpy change of neutralization - H neut The heat change when an amount of acid neutralizes a base to form 1 mole of water (in dilute aqueous solution) at standard conditions. KOH(aq) + HNO3(aq) KNO3(aq) + H2O(l) = H r H neut Standard enthalpy change of atomization - H atom The heat change when 1 mole of atoms in the gas phase is formed from the element in the defined physical state under standard conditions. H2(g) H(g) ato [H2(g = H r H m )] Standard enthalpy change of solution - H
sol n
Second electron affinity 2 EA The energy change when 1 mole of electrons are added to 1 mole of gaseous X ions to form 1 mole of gaseous X ions
2-
Cl (g) + e Cl nd (g) H r = 2 EA [Cl] Lattice energy - |LE| The heat change when 1 mole of pure solid ionic compound is formed from its constituent gaseous ions under standard conditions Mg (g) + 2Cl (g) MgCl (s)
+ 2 -
2-
The heat change when 1 mole of solute is completely dissolved in enough solvent so that no further heat
IO NI C E QUI LB R I A Brnsted-Lowry theory of acids and bases A acid is a proton donor. A base is a proton acceptor. An acid-base reaction involves the transfer of a proton from an acid to a base. K I N E T I C S Rate Equation A mathematical equation that shows how the rate of reaction is dependent on the concentrations of the reactants. It relates the rate of reaction to the concentrations of the reactants raised to the appropriate power. Rate constant k A proportionality constant in the rate equation of the reaction Order of reaction w.r.t. a reactant The power to which the concentration of that reagent is raised in the rate equation Overall order or reaction The sum of all powers concentrations of reactants are raised in the rate equation Strong acid An acid which undergoes complete dissociation in aqueous solution Weak acid An acid which undergoes partial dissociation in aqueous solution
Strong base A base which undergoes complete ionization in aqueous solution Weak base A base which undergoes partial ionization in aqueous solution Degree of ionization The fraction of molecules which is ionized at equilibrium
to
which
Buffer solution A solution which is able to resist a change in pH upon the addition of a small amount of acid or base E L E C T R O C H E M I S T R Y Standard electrode potential E The potential of a half-cell relative to a standard hydrogen half-cell under standard conditions Standard cell potential E
Half-life t The time required for the concentration of a limiting reagent to decrease to half of its initial concentration C H E M I C A L E Q U I L I B R IA Reversible reaction Reactions that take place directions at comparable rates
in
both
Static equilibrium A state in which there is no change in both macroscopic and microscopic properties in a system
The potential difference between two halfDynamic cells under equilibrium standard conditions A reversible reaction in which the rate of the forward and backward reactions are equal and Apparent molecular nonzero. mass Mapp The weighted average of Degree of molecular masses dissociation of all gases present in The fraction of a reactant that has equilibrium dissociated at a particular temperature
cell
the
relative
Le Chateliers Principle states that if a system in equilibrium is subjected to a change which disturbs the equilibrium, the system responds in such a way as to counteract the effect of the change.
T RAN SIT IO N ME T AL S Transition metal A metal which forms one or more stable ions which have incompletely filled dsubshells Compl ex A complex contains a central metal ion linked to one or more surrounding ligands. Liga nd An anion or a molecule which contains at least one atom bearing one lone pair of electrons which can be donated into the lowlying vacant orbital of the central metal atom/ion forming a dative bond.
ORGANIC CHEMISTRY
n = C (H + X N) + 1 Note the difference between benzyl and phenyl Phenyl is just a C H group
6 5
Benzyl has a CH
group attached to C H
2 6 5
ARENES
Reactivity of attached groups and how they direct. Activiati More reactive ng Amin -NH2 e -OH Hydro (CH2)nCH3 xy C6H5 Alkyl H Aryl -Cl, -Br, -I reference! Aldehyde -CHO Este -COOr Carboxylic -COOH acid Ketone -CONitrile -CN Nitrite -NO Carbons that are definitely not chiral 2 3 sp hybridized : triple bonded Deactivati Less reactive 2 sp hybridized: double bonded or part of a benzene ring n chiral centres give 2 optical isomers
n
p Pa atm
V 3 m 3 dm
R 8.31 J 0.082
The partial pressure of a gas is its mole fraction times its total pressure The mole fraction is given by ngas/ntotal
STEREOISOMERISM
evin. Distributed on Erpz.net.
3 directing
pV=n RT
2,4 Directing
DISTINGUISHING TESTS
Remember to give the following 1. Reagents and conditions 2. Observations 3. Equations
MECHANISM DRAWING
1. 2. 3. 4. 5. Name the mechanism e.g. electrophilic addition Show the polarization of atoms e.g. Br Br Draw arrows showing flow of electrons Label slow/fast steps Except in FRS and SN2 Number your steps
CHEMICAL BONDING
Strong covalent bonds Have multiple bonds Have short bond length and more effective orbital overlap (small molecular size) Are more polar have ionic character Strong ionic bonds Have high lattice energy o Large charges o Small radii