Cambridge International A Level Chemistry Answers to end-of-chapter questions

Answers to EOCQs
Chapter 30 for curly arrow from C=O to between O
and H atoms [1]
1 a i 2-hydroxypropanoic acid [1] for curly arrow from H–O bond onto oxygen
ii OH
[1]
for products [1]
C Question 1 part d i asks you for a
H CH3 mechanism you probably haven’t studied.
HOOC [1] Think logically and use what you know
Question 1 part a ii asks you to draw the from other topics and from the question:
other optical isomer of lactic acid. To help 1 The reaction involves addition of 2H
yourself to get it right, redraw the isomer to a ketone – the mechanism will be
of lactic acid shown here on the left-hand nucleophilic addition.
side of a sheet of paper, then put a vertical 2 The question says that the first step
mirror line down the centre of the paper. involves nucleophilic attack on the
Now draw the other isomer. Start with a C carbon of the ketone group by an H– ion.
in the middle and a vertical bond to an OH 3 The question says that there is water
– this doesn’t change. Then draw in the present.
other three groups. In the first isomer they ii CH3COCOOH is planar around the carbonyl
were (left to right) –CH3, –COOH, –H. In the carbon and there is attack from hydride
second isomer they will be –H, –COOH, above and below plane of molecule; [1]
–CH3. The forward/backwards direction this gives equal amounts of the two optical
of their bonds doesn’t change. The –H is isomers of CH3CH(OH)COOH.[1]
going backwards, the –COOH is coming These cancel each other out, so there is no
forwards, the –CH3 is neither backwards rotation of plane-polarised light. [1]
nor forwards. e i Each molecule of lactic acid contains an
iii It has a chiral carbon atom / four different alcohol/–OH group
groups bonded to same carbon atom. [1] and a carboxylic acid/–COOH group, [1]
b i acidified potassium dichromate; [1] which react with each other / form an ester
heat/distil[1] link between the monomers. [1]
ii CH3CH(OH)COOH + [O] → CH3COCOOH + H2O ii condensation polymerisation [1]
[2] iii CH3 O
[1 mark for reactants, 1 mark for products] O CH C
c i sodium tetrahydridoborate(III) /
borohydride / NaBH4;[1] [1]
Total = 23
warm[1]
ii CH3COCOOH + 2[H] → CH3CH(OH)COOH[2] 2 Step 1, preparation of 2-bromopropanoic
[1 mark for reactants, 1 mark for products] acid:
d i δ– OH
CH3CH(OH)COOH + HBr → CH3CHBrCOOH + H2O
O H O
δ+ [2]
H 3C C H H3C C COOH + H O–
[1 mark for reactants, 1 mark for products]
COOH
–H H reagents used are:
for dipoles [1] concentrated sulfuric acid [1]
for curly arrow from lone-pair electrons on and sodium (or potassium) bromide [1]
hydride[1]

Cambridge International AS and A Level Chemistry © Cambridge University Press 2014

 Cambridge International A Level Chemistry Answers to end-of-chapter questions

Step 2, preparation of 2-aminopropanoic 5 a i octane (C8H18)[1]

acid: C10H22 → C8H18 + C2H4 [2]
CH3CHBrCOOH + NH3 ii cracking[1]
 → CH3CH(NH2)COOH + HBr b i ethanol[1]
[2] C2H5OH → C2H4 + H2O[2]
[1 mark for reactants, 1 mark for products]
reagents and conditions are: ii elimination/dehydration[1]
Total = 8
in ethanol (as solvent); [1]
heat[1]
in sealed tube (or under pressure) [1]
Total = 9

3 a A chiral auxiliary is a group or molecule

attached to the compound from which the
chiral compound is formed. [1]
The auxiliary ensures that during the
chemical synthesis only one optical isomer
can be made. [1]
At the end of the synthesis the auxiliary
molecule is removed. [1]
b Use naturally occurring chiral molecules [1]
that have a similar chirality to the compound
required;[1]
for example, sugars and amino acids. [1]
Total = 6

4 a O

N O
N
H
O O [1]
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

Cambridge International AS and A Level Chemistry © Cambridge University Press 2014