42
Organic chemistry
29 An introduction to A Level organic chemistry
Homologous series Name of functional Structural formula of Displayed formula Skeletal formula Name
group functional group
*n/a
arene arene benzene
X X
*n/a chlorobenzene
halogenoarene halogen
(when X = Cl )
www.cambridgeinternational.org/alevel
OH OH
*n/a
phenol phenol phenol
H H
O O O
acyl chloride acyl chloride H C C C propanoyl chloride
R C Cl Cl
H H Cl
H H H
H N (naming of secondary
amines (secondary R N
amine H C N C H and tertiary amines is
and tertiary)
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
R H not required)
H H
H H O O
O H
amide (primary,
amide H C C C N propanamide
secondary and tertiary) R C NH2 H NH2
H H
O H
O H O
amino acid amine and carboxyl HO C C N NH2 2-aminoethanoic acid
HO C CHRNH2 H HO
H
*where a benzene ring is part of the molecule, a displayed formula would not be expected to be drawn.
Back to contents page
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
29.1 Formulae, functional groups and the naming of organic compounds
Learning outcomes
Candidates should be able to:
1 understand that the compounds in the table on page 42 contain a functional group which dictates their
physical and chemical properties
2 interpret and use the general, structural, displayed and skeletal formulae of the classes of compound stated
in the table on page 42
3 understand and use systematic nomenclature of simple aliphatic organic molecules (including cyclic
compounds containing a single ring of up to six carbon atoms) with functional groups detailed in the table
on page 42, up to six carbon atoms (six plus six for esters and amides, straight chains only for esters and
nitriles)
4 understand and use systematic nomenclature of simple aromatic molecules with one benzene ring and one
or more simple substituents, for example 3-nitrobenzoic acid or 2,4,6-tribromophenol
29.2 Characteristic organic reactions
Learning outcomes
Candidates should be able to:
1 understand and use the following terminology associated with types of organic mechanisms:
(a) electrophilic substitution
(b) addition-elimination
29.3 Shapes of aromatic organic molecules; σ and π bonds
Learning outcomes
Candidates should be able to:
1 describe and explain the shape of benzene and other aromatic molecules, including sp2 hybridisation, in
terms of σ bonds and a delocalised π system
29.4 Isomerism: optical
Learning outcomes
Candidates should be able to:
1 understand that enantiomers have identical physical and chemical properties apart from their ability to
rotate plane polarised light and their potential biological activity
2 understand and use the terms optically active and racemic mixture
3 describe the effect on plane polarised light of the two optical isomers of a single substance
4 explain the relevance of chirality to the synthetic preparation of drug molecules including:
(a) the potential different biological activity of the two enantiomers
(b) the need to separate a racemic mixture into two pure enantiomers
(c) the use of chiral catalysts to produce a single pure optical isomer
(Candidates should appreciate that compounds can contain more than one chiral centre, but knowledge of
meso compounds and nomenclature such as diastereoisomers is not required.)
Back to contents page www.cambridgeinternational.org/alevel 43
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
30 Hydrocarbons
30.1 Arenes
Learning outcomes
Candidates should be able to:
1 describe the chemistry of arenes as exemplified by the following reactions of benzene and methylbenzene:
(a) substitution reactions with Cl 2 and with Br2 in the presence of a catalyst, AlCl 3 or Al Br3, to form
halogenoarenes (aryl halides)
(b) nitration with a mixture of concentrated HNO3 and concentrated H2SO4 at a temperature between
25 °C and 60 °C
(c) Friedel–Crafts alkylation by CH3Cl and AlCl 3 and heat
(d) Friedel–Crafts acylation by CH3COCl and AlCl 3 and heat
(e) complete oxidation of the side-chain using hot alkaline KMnO4 and then dilute acid to give a benzoic
acid
(f) hydrogenation of the benzene ring using H2 and Pt/Ni catalyst and heat to form a cyclohexane ring
2 describe the mechanism of electrophilic substitution in arenes:
(a) as exemplified by the formation of nitrobenzene and bromobenzene
(b) with regards to the effect of delocalisation (aromatic stabilisation) of electrons in arenes to explain the
predomination of substitution over addition
3 predict whether halogenation will occur in the side-chain or in the aromatic ring in arenes depending on
reaction conditions
4 describe that in the electrophilic substitution of arenes, different substituents direct to different ring
positions (limited to the directing effects of –NH2, –OH, –R, –NO2, –COOH and –COR)
31 Halogen compounds
31.1 Halogen compounds
Learning outcomes
Candidates should be able to:
1 recall the reactions by which halogenoarenes can be produced: substitution of an arene with Cl2 or Br2
in the presence of a catalyst, Al Cl3 or Al Br3 to form a halogenoarene, exemplified by benzene to form
chlorobenzene and methylbenzene to form 2-chloromethylbenzene and 4-chloromethylbenzene
2 explain the difference in reactivity between a halogenoalkane and a halogenoarene as exemplified by
chloroethane and chlorobenzene
32 Hydroxy compounds
32.1 Alcohols
Learning outcomes
Candidates should be able to:
1 describe the reaction with acyl chlorides to form esters using ethyl ethanoate
44 www.cambridgeinternational.org/alevel Back to contents page
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
32.2 Phenol
Learning outcomes
Candidates should be able to:
1 recall the reactions (reagents and conditions) by which phenol can be produced:
(a) reaction of phenylamine with HNO2 or NaNO2 and dilute acid below 10 °C to produce the diazonium
salt; further warming of the diazonium salt with H2O to give phenol
2 recall the chemistry of phenol, as exemplified by the following reactions:
(a) with bases, for example NaOH(aq) to produce sodium phenoxide
(b) with Na(s) to produce sodium phenoxide and H2(g)
(c) in NaOH(aq) with diazonium salts, to give azo compounds
(d) nitration of the aromatic ring with dilute HNO3(aq) at room temperature to give a mixture of
2-nitrophenol and 4-nitrophenol
(e) bromination of the aromatic ring with Br2(aq) to form 2,4,6-tribromophenol
3 explain the acidity of phenol
4 describe and explain the relative acidities of water, phenol and ethanol
5 explain why the reagents and conditions for the nitration and bromination of phenol are different from those
for benzene
6 recall that the hydroxyl group of a phenol directs to the 2-, 4- and 6-positions
7 apply knowledge of the reactions of phenol to those of other phenolic compounds, e.g. naphthol
33 Carboxylic acids and derivatives
33.1 Carboxylic acids
Learning outcomes
Candidates should be able to:
1 recall the reaction by which benzoic acid can be produced:
(a) reaction of an alkylbenzene with hot alkaline KMnO4 and then dilute acid, exemplified by
methylbenzene
2 describe the reaction of carboxylic acids with PCl 3 and heat, PCl 5, or SOCl 2 to form acyl chlorides
3 recognise that some carboxylic acids can be further oxidised:
(a) the oxidation of methanoic acid, HCOOH, with Fehling’s reagent or Tollens’ reagent or acidified KMnO4
or acidified K2Cr2O7 to carbon dioxide and water
(b) the oxidation of ethanedioic acid, HOOCCOOH, with warm acidified KMnO4 to carbon dioxide
4 describe and explain the relative acidities of carboxylic acids, phenols and alcohols
5 describe and explain the relative acidities of chlorine-substituted carboxylic acids
33.2 Esters
Learning outcomes
Candidates should be able to:
1 recall the reaction by which esters can be produced:
(a) reaction of alcohols with acyl chlorides using the formation of ethyl ethanoate and phenyl benzoate as
examples
Back to contents page www.cambridgeinternational.org/alevel 45
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
33.3 Acyl chlorides
Learning outcomes
Candidates should be able to:
1 recall the reactions (reagents and conditions) by which acyl chlorides can be produced:
(a) reaction of carboxylic acids with PCl 3 and heat, PCl 5, or SOCl 2
2 describe the following reactions of acyl chlorides:
(a) hydrolysis on addition of water at room temperature to give the carboxylic acid and HCl
(b) reaction with an alcohol at room temperature to produce an ester and HCl
(c) reaction with phenol at room temperature to produce an ester and HCl
(d) reaction with ammonia at room temperature to produce an amide and HCl
(e) reaction with a primary or secondary amine at room temperature to produce an amide and HCl
3 describe the addition-elimination mechanism of acyl chlorides in reactions in 33.3.2(a) – (e)
4 explain the relative ease of hydrolysis of acyl chlorides, alkyl chlorides and halogenoarenes (aryl chlorides)
34 Nitrogen compounds
34.1 Primary and secondary amines
Learning outcomes
Candidates should be able to:
1 recall the reactions (reagents and conditions) by which primary and secondary amines are produced:
(a) reaction of halogenoalkanes with NH3 in ethanol heated under pressure
(b) reaction of halogenoalkanes with primary amines in ethanol, heated in a sealed tube / under pressure
(c) the reduction of amides with LiAl H4
(d) the reduction of nitriles with LiAl H4 or H2 / Ni
2 describe the condensation reaction of ammonia or an amine with an acyl chloride at room temperature to
give an amide
3 describe and explain the basicity of aqueous solutions of amines
34.2 Phenylamine and azo compounds
Learning outcomes
Candidates should be able to:
1 describe the preparation of phenylamine via the nitration of benzene to form nitrobenzene followed by
reduction with hot Sn/concentrated HCl , followed by NaOH(aq)
2 describe:
(a) the reaction of phenylamine with Br2(aq) at room temperature
(b) the reaction of phenylamine with HNO2 or NaNO2 and dilute acid below 10 °C to produce the
diazonium salt; further warming of the diazonium salt with H2O to give phenol
3 describe and explain the relative basicities of aqueous ammonia, ethylamine and phenylamine
4 recall the following about azo compounds:
(a) describe the coupling of benzenediazonium chloride with phenol in NaOH(aq) to form an azo compound
(b) identify the azo group
(c) state that azo compounds are often used as dyes
(d) that other azo dyes can be formed via a similar route
46 www.cambridgeinternational.org/alevel Back to contents page
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
34.3 Amides
Learning outcomes
Candidates should be able to:
1 recall the reactions (reagents and conditions) by which amides are produced:
(a) the reaction between ammonia and an acyl chloride at room temperature
(b) the reaction between a primary amine and an acyl chloride at room temperature
2 describe the reactions of amides:
(a) hydrolysis with aqueous alkali or aqueous acid
(b) the reduction of the CO group in amides with LiAl H4 to form an amine
3 state and explain why amides are much weaker bases than amines
34.4 Amino acids
Learning outcomes
Candidates should be able to:
1 describe the acid / base properties of amino acids and the formation of zwitterions, to include the isoelectric
point
2 describe the formation of amide (peptide) bonds between amino acids to give di- and tripeptides
3 interpret and predict the results of electrophoresis on mixtures of amino acids and dipeptides at varying pHs
(the assembling of the apparatus will not be tested)
35 Polymerisation
35.1 Condensation polymerisation
Learning outcomes
Candidates should be able to:
1 describe the formation of polyesters:
(a) the reaction between a diol and a dicarboxylic acid or dioyl chloride
(b) the reaction of a hydroxycarboxylic acid
2 describe the formation of polyamides:
(a) the reaction between a diamine and a dicarboxylic acid or dioyl chloride
(b) the reaction of an aminocarboxylic acid
(c) the reaction between amino acids
3 deduce the repeat unit of a condensation polymer obtained from a given monomer or pair of monomers
4 identify the monomer(s) present in a given section of a condensation polymer molecule
35.2 Predicting the type of polymerisation
Learning outcomes
Candidates should be able to:
1 predict the type of polymerisation reaction for a given monomer or pair of monomers
2 deduce the type of polymerisation reaction which produces a given section of a polymer molecule
Back to contents page www.cambridgeinternational.org/alevel 47
Cambridge International AS & A Level Chemistry 9701 syllabus for 2022, 2023 and 2024. Subject content
35.3 Degradable polymers
Learning outcomes
Candidates should be able to:
1 recognise that poly(alkenes) are chemically inert and can therefore be difficult to biodegrade
2 recognise that some polymers can be degraded by the action of light
3 recognise that polyesters and polyamides are biodegradable by acidic and alkaline hydrolysis
36 Organic synthesis
36.1 Organic synthesis
Learning outcomes
Candidates should be able to:
1 for an organic molecule containing several functional groups:
(a) identify organic functional groups using the reactions in the syllabus
(b) predict properties and reactions
2 devise multi-step synthetic routes for preparing organic molecules using the reactions in the syllabus
3 analyse a given synthetic route in terms of type of reaction and reagents used for each step of it, and
possible by-products
Analysis
37 Analytical techniques
37.1 Thin-layer chromatography
Learning outcomes
Candidates should be able to:
1 describe and understand the terms
(a) stationary phase, for example aluminium oxide (on a solid support)
(b) mobile phase; a polar or non-polar solvent
(c) Rf value
(d) solvent front and baseline
2 interpret Rf values
3 explain the differences in Rf values in terms of interaction with the stationary phase and of relative solubility
in the mobile phase
37.2 Gas / liquid chromatography
Learning outcomes
Candidates should be able to:
1 describe and understand the terms
(a) stationary phase; a high boiling point non-polar liquid (on a solid support)
(b) mobile phase; an unreactive gas
(c) retention time
2 interpret gas / liquid chromatograms in terms of the percentage composition of a mixture
3 explain retention times in terms of interaction with the stationary phase
48 www.cambridgeinternational.org/alevel Back to contents page
