CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

Exam-style questions and sample answers have been written by the authors. In examinations, the way marks are awarded
may be different.

Coursebook answers
Chapter 29
Science in context
Ask learners to work in small groups to discuss b points to include:
the development of new medicinal drugs. Points • r acemic mixture produced in
covered should be the importance of computers traditional synthetic routes
in analysing data to discover the structure of
pathogens, as well as their role in the modelling • t his results in the need to separate
of potential drugs to fit into, bond with and the mixture of enantiomers
deactivate the active site on the pathogen. • t his can use large volumes of
Discuss the ‘trial and error’ methods used and organic solvents, which have to
compare them with modern modelling techniques be disposed of, along with the
in a whole class plenary. Scientists can design unwanted enantiomer
specifically shaped molecules that can block • t he process will also use more
active sites on enzymes and molecules and so chemicals, which require natural
interfere with the reproduction of a virus within its resources
host cell. However, even with modern technology • enzymes are stereospecific
and our ability to determine the genetic code of
a pathogen, the search for an effective anti-viral •  hole organisms can be used
w
drug or for a vaccine to combat a new virus is (without having to isolate enzymes)
both time-consuming, often involving large teams • f ewer steps in process, resulting in
of scientists and extensive tests to ensure patient more efficiency
safety, and is inevitably a very costly process.
c Thalidomide was prescribed to
Note that the Science in Context passage in pregnant women as a sedative during
Chapter 30 covers the founder of the ribbon the early 1960s. It was for a time the
diagrams shown in Figure 29.2. preferred sedative during pregnancy as
the alternatives, such as valium, were
Self-assessment questions addictive. Unfortunately, one of the two
optical isomers of thalidomide proved
1 a i less dosage required; reduces risk to have disastrous side effects, causing
of side effects as the unwanted babies to be born with congenital
enantiomer might present a health deformities (teratogenicity). Not
hazard surprisingly, thalidomide was quickly
ii reduces the chances of litigation withdrawn from use and law-suits
against the drug company as a were filed against the manufacturers to
result of side effects caused by the compensate those affected and to help
unwanted enantiomer; possibly finance their care. If the optical isomer
cheaper as don’t waste the that had therapeutic effects, without
unwanted enantiomer side effects, had been purified and given
as a medicine, this still wouldn’t have
solved the problem. The ‘good’ optical
isomer is converted into the ‘bad’
optical isomer in the body, with the
same outcome.

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

2 a H2C CH2 H
HCl(aq) HO N CCH3 + H2O
CH3CH2Cl O
heat with alcoholic

⎯→
ammonia under pressure
CH3CH2NH2
HO NH2 + CH3COOH
b
CHO
ii hydrolysis
heat with H2SO4(aq) and
K2Cr2O7(aq) c A = sodium propanoate; B =
propanoic acid; C = propanoyl
CO2H chloride; D = propanamide
heat with ethanol d i Stage 1: add conc. nitric acid
and acid catalyst and conc. sulfuric acid to make
nitrobenzene
CO2CH2CH3
Stage 2: add tin / conc.
hydrochloric acid to reduce
c CH3CH2CH2CH2Br
nitrobenzene to phenylamine
reflux with
NaOH(aq) Step 3: add sodium nitrate(III)
and hydrochloric acid, followed
CH3CH2CH2CH2OH
by sodium hydroxide solution, at
reflux with H2SO4(aq)
a temperature between 0 oC and
and excess K2Cr2O7(aq)
5 oC to phenylamine
CH3CH2CH2COOH
ii add phenol in aqueous sodium
d CH3CH2COCH3 hydroxide
warm with LiAlH4 iii D
in dry ether
CH3CH2CHOHCH3 Exam-style questions
distil from mixture
with conc. H2SO4 and KBr(s) 1 a i 2-hydroxypropanoic acid [1]
CH3CH2CHBrCH3 ii OH [1]
heat with
alcoholic NH3 C
CH3CH2CHNH2CH3 H CH3
HOOC
3 a i carboxylic acid and ester
ii hydroxy / alcohol / phenol and amide Question 1 part a ii asks you to
b i aspirin: draw the other optical isomer of
COOH lactic acid. To help yourself to
+ H2O get it right, redraw the isomer
OCOCH3 of lactic acid shown here on the
left-hand side of a sheet of paper,
then put a vertical mirror line
⎯→

down the centre of the paper.

Now draw the other isomer.
COOH Start with a C in the middle and
+ CH3COOH a vertical bond to an OH – this
OH doesn’t change. Then draw in the
paracetamol: other three groups. In the first
isomer they were (left to right)

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

—CH3, —COOH, —H. In the The question says that there is

second isomer they will be —H, water present.
—COOH, —CH3. The forward /
CH3COCOOH is planar around
backwards direction of their the carbonyl carbon and there is
bonds doesn’t change. The —H is attack from hydride above and
going backwards, the —COOH below plane of molecule; [1]
is coming forwards, the —CH3 is
neither backwards nor forwards. this gives equal amounts of
the two optical isomers of
iii It has a chiral carbon atom / four CH3CH(OH)COOH.[1]
different groups bonded to same
carbon atom. [1] These cancel each other out, so
there is no rotation of plane-
b i acidified potassium dichromate; [1] polarised light. [1]
heat / distil [1] e i Each molecule of lactic acid
ii CH3CH(OH)COOH + [O] → contains an alcohol / —OH group
CH3COCOOH + H2O [2] and a carboxylic acid / —COOH
[1 mark for reactants, 1 mark for group,[1]
products] which react with each other /
c i sodium tetrahydridoborate(III) / form an ester link between the
borohydride / NaBH4;[1] monomers.[1]
warm[1] ii condensation polymerisation [1]
ii CH3COCOOH + 2[H] → iii CH3 O [1]
CH3CH(OH)COOH [2]
O CH C
[1 mark for reactants, 1 mark for
products]
d i δ–
[Total: 23]
O H O OH

H3C
δ+
C H H3C C COOH + H O–
2 Step 1, preparation of 2-bromopropanoic
COOH acid:
H
H–
CH3CH(OH)COOH + HBr →
for dipoles [1]  CH3CHBrCOOH + H2O [2]
for curly arrow from lone-pair [1 mark for reactants, 1 mark for products]
electrons on hydride [1] reagents used are:
for curly arrow from C═O to concentrated sulfuric acid [1]
between O and H atoms [1]
and sodium (or potassium) bromide [1]
for curly arrow from H—O bond
Step 2, preparation of 2-aminopropanoic acid:
onto oxygen [1]
CH3CHBrCOOH + NH3 →
for products [1]
 CH3CH(NH2)COOH + HBr [2]
ii Question 1 part d i asks you for a
[1 mark for reactants, 1 mark for products]
mechanism you probably haven’t
studied. Think logically and use reagents and conditions are:
what you know from other topics in ethanol (as solvent); [1]
and from the question:
heat[1]
The reaction involves addition of
in sealed tube (or under pressure) [1]
2H to a ketone – the mechanism
will be nucleophilic addition. [Total: 9]
The question says that the first
step involves nucleophilic attack
on the carbon of the ketone group
by an H− ion.

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

3 a O [1]

N O
N
H
O O
b amine (allow amino); [1]
ketone[1]
c reduction;[1]
add an aqueous solution of NaBH4 or
LiAlH4 in dry ether [1]
d Each enantiomer differs in its
‘pharmaceutical activity’ / one
enantiomer might be effective but the
other could induce serious side effects; [1]
minimises the risk of side effects /
reduces the patient’s dosage / the pure
enantiomer is more potent / has better
therapeutic activity [1]
cuts costs of production as less drug
is needed / protects companies from
possible legal action (litigation) for
damages by patients who suffer bad
side effects. [1]
[Total: 8]
4 a i octane (C8H18)[1]
C10H22 → C8H18 + C2H4[2]
ii cracking[1]
b i ethanol[1]
C2H5OH → C2H4 + H2O[2]
ii elimination / dehydration [1]
[Total: 8]

4 Cambridge International AS & A Level Chemistry © Cambridge University Press 2020