CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

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Coursebook answers
Chapter 30
Exam-style questions
The ‘Analytical techniques’ section involves less e Can quickly provide an accurate
knowledge to recall than other chapters, but measure of the quantity of any
it does contain ideas and skills that you must anabolic steroid present;  [1]
learn how to apply. Practise these questions, and the amounts present are small and
the self-assessment questions in the text, until gas–liquid chromatography is very
you are confident in applying ideas and skills. sensitive. [1]
Questions 2, 3, 4 and 5 are good examples of this.
f The compounds can be identified
1 a A = recorder response [1] immediately by their fragmentation
B = time of injection [1] patterns; [1]
C = retention time [1] compare results to database or there is

( )
1 no need for running standards in order
b total area × 2 × 50  [1] to identify the unknowns. [1]
2

+( × 1 × 80 ) 
1 [1] g They are large compounds with large
2 relative molecular masses; [1]

+( × 2 × 60 )  they have high boiling points and

1 [1]
2 therefore are not volatile enough for
= 150 [1] separation using this method. [1]

percentage of pentan-1-ol = 50 [Total: 21]

× 100% [1]
150
2 a
= 33.3 % [1]
Element carbon hydrogen oxygen
c The stationary phase is non-polar; [1]
Percentage 62.1 10.3 27.6
the less polar compounds are
adsorbed more strongly on the column Mass in 62.1 g 10.3 g 27.6 g
and have longer retention times; [1] 100 g

octane has more electrons than Number of 62.1 10.3 27.6

= 5.18 = 10.3 = 1.73
pentane so stronger van der Waals’ moles 12.0 1.0 16.0

forces between octane and column. [1] Relative 5.18 10.3 1.73
=3 =6 =1
d i T
 he order would be reversed / number of 1.73 1.73 1.73
changed (and overall retention atoms
times would increase). [1]  [1]
ii The pentan-1-ol is the most polar empirical formula = C3H6O [1]
molecule [1]
b molecular mass is 58 [1]
and would be retained the longest. [1]
empirical formula mass = molecular
mass, therefore the molecular formula
= C3H6O [1]

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

c i H O H  [1] b The m/e value for the penultimate

peak on the mass spectrum = 106; [1]
H C C C H propanone
this is twice the empirical formula mass,
H H so the molecular formula is C8H10. [1]
H H H
H H  [1] c i
O H C C H H C
propanal H H HH
H C C C C
H H
H H H
H
ii it is propanal [1] H C H H
iii There are three peaks present in H
H C C C H
the 1H NMR spectrum; [1]
H H H H
propanone has only one type of proton [1] [4]

and therefore it would have only [1 mark for each structure]

one peak. [1] ii H H  [1]
d —
This is the peak for the CH3 protons;[1] H C C H
it is split into a triplet because of
the two chemically different (non- H H
equivalent) protons on the adjacent This is because when chlorinated by
carbon (by applying the n + 1 rule in electrophilic aromatic substitution it
which n = 2). [1] forms only the following compound:
e i three lines as there are three Cl
H H  [1]
non-equivalent carbon atoms in
propanal [1] H C C H
the methyl carbon (—CH3), the H H
central carbon atom (—CH2, and the
carbonyl carbon (>C═O) [1] The other possible isomers form
several different compounds. [1]
ii two lines as there are two non-
equivalent carbon atoms in The H NMR spectrum shows two
1

propanone [1] peaks as C has only two different

types of proton; [1]
the two (equivalent) methyl carbons
(—CH3), and the central carbon the other possible isomers have larger
atom / carbonyl carbon (—C═O) [1] numbers of different types of proton. [1]

[Total: 16] d The peak at δ = 7 ppm [1]

is the peak from the benzene ring
3 a Element carbon hydrogen protons; [1]
Percentage 90.6 9.4
the peak at δ = 2.3 ppm [1]
Mass in 100 g 90.6 g 9.4 g
corresponds to the —CH3 protons. [1]
Number of 90.6 9.4
= 7.55 = 9.4 [Total: 17]
moles in 100 g 12.0 1.0

Relative 7.55 9.4

=1 = 1.25
number of 7.55 7.55
atoms
Whole 4 5
numbers

 [1]
empirical formula = C4H5 [1]

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

4 a but the 1H NMR spectrum of D has

three peaks, corresponding to the
Element carbon hydrogen oxygen
three different types of proton in D. [1]
Percentage 77.8 7.41 14.8
d There are three peaks because of the
Mass in 100 g 77.8 g 7.41 g 14.8 g three chemically different types of
Number 77.8 7.41 14.8 proton in D: [1]
= 6.48 = 7.41 = 0.925
of moles 12.0 1.0 16.0 the peak for five protons at δ = 7.3
in 100 g ppm is caused by the five benzene
Relative 6.48 7.41 0.925 protons; [1]
=7 =8 =1
number of 0.925 0.925 0.925 [Total: 15]
atoms
5 a
 [1]
Element carbon hydrogen oxygen
empirical formula = C7H8O [1]
Percentage 69.8 11.6 18.6
b The m/e value for the molecular-ion
peak is 108; [1] Mass in 69.8 g 11.6 g 18.6 g
100 g
this corresponds to the mass of the
Number 69.8 11.6 18.6
empirical formula, = 5.82 = 11.6 = 1.16
of moles in 12.0 1.0 16.0
so molecular formula = empirical 100 g
formula = C7H8O. [1]
Relative 5.82 11.6 11.6
=5 = 10 =1
number of 1.16 1.16 11.6
c i H
atoms
O
H H H  [1]
H C O H C empirical formula = C5H10O [1]
H H b The m/e value for the molecular-ion
peak is 86 so its relative molecular
H
O
H mass is 86; [1]
this is the same as the empirical
H C
formula mass, so the molecular
H formula is also C5H10O. [1]
H c H H H H H H H
H H
H C H H H H C C C C C H C C C C
H H H H O H H O
O C O H C H

H  [5] H
H H H H
[1 mark for each structure]
H C C C C
ii H H [1]
H H O
C O H C H

H
H
H
iii The relative area of the peak at
δ = 7.3 ppm is 5, so there are H C H H H H
O
five protons on the benzene H H
H C C C C H
ring; therefore D cannot be a H C C C
C
disubstituted compound. [1] H H H
H O H H
The other mono-substituted H C H
compound has only two types of
proton [1] H

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

H H
H H O
O
H C C C H
H C C C H
H C
H C H
H H H C H H
C H
H H H

 [7]
[1 mark for each structure]
d It must have a carbonyl group,
because of the positive result with
2,4-DNPH. [1]
It is an aldehyde, because of the
positive result from the silver
mirror test. [1]
On the NMR spectrum there is
an absorption at δ = 9.5 ppm,
characteristic of the aldehyde —CHO
proton. [1]
e On the 1H NMR spectrum there
is an absorption at δ = 9.5 ppm,
characteristic of the aldehyde —CHO
proton; [1]
it has only two distinct peaks and
therefore only two types of proton; [1]
therefore E must be
H

H C H
H
H
H C C C

H O
H C H

H  [1]
There is no splitting of the peaks
because there are no adjacent carbons
with chemically different protons on
them. [1]
[Total: 18]

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