Answers to end-of-chapter questions

Chapter 29

Examiners tip

The Applications of chemistry section involves less

knowledge to recall than the other sections of the
syllabus, but it does contain ideas and skills that you
must learn how to apply. Practise these questions, and
the check-up questions in the text, until you are confident
in applying ideas and skills. Questions 4, 5, 6 and 7 are
good examples of this. You may not have encountered
compounds B, C, D, and E before, and you are certainly
not expected to recognise their mass spectra, or to be
able to recall the answers to the questions here. But
you should be able to use the ideas and skills that you
have learned, in order to get the correct answers to
the questions.

1 a i due to CH3+
ii due to OH+
iii due to CH2OH+
iv due to CH3CO+
v due to CH3COCH2+
vi due to HOCH2CO+
b m/e = 74

[1]
[1]
[1]
[1]
[1]
[1]
[1]
Total = 7

2 a A = recorder response
B = time of injection
C = retention time

[1]
[1]
[1]

b total area = (12 2 50)

[1]

+ (12 1 80)

[1]

+ (12 2 60)

[1]

= 150

[1]

percentage of pentan-1-ol =

50
100%
150

= 33.3%
c the stationary phase is non-polar;
the less polar compounds are adsorbed more
strongly on the column and have longer
retention times;
octane has more electrons than pentane so
stronger van der Waals forces between octane
and column
d i The order would be reversed/changed (and
overall retention times would increase).
ii The pentan-1-ol is the most polar molecule
and would be retained the longest.

AS and A Level Chemistry Cambridge University Press

[1]
[1]
[1]
[1]
[1]
[1]
[1]
[1]

e anabolic steroids are non-polar compounds

that are volatile;
[1]
the amounts present are small and gasliquid
chromatography is very sensitive
[1]
f the compounds can be identified immediately
by their fragmentation patterns;
[1]
compare results to database or there is no
need for running standards in order to
identify the unknowns
[1]
g they are large compounds with large relative
molecular masses;
[1]
they have high boiling points and therefore
are not volatile enough for separation using
this method
[1]
Total = 21

3 a The sample is spotted onto paper at the

marked point and then placed in solvent 1
[1]
and the chromatogram is run in solvent 1.
[1]
The paper is taken out and turned
through 90
[1]
and is then run again in solvent 2.
[1]
b C, D and E
[1]
A and G
[1]
c made visible by using ninhydrin spray
[1]
2.7
d i Rf =
= 0.75
[1]
3.6
0.9
ii Rf =
= 0.225
[1]
4.0
e A and C
[1]
3.0
f i Rf (X) =
= 0.214
[1]
14.0
8.0
Rf (Y) =
= 0.571
[1]
14.0
10.0
Rf (Z) =
= 0.714
[1]
14.0
ii Mobile phase is solvent used;
[1]
stationary phase is water between
the cellulose fibres of the paper.
[1]
The amino acids are partitioned between
the stationary phase and the mobile phase. [1]
The more soluble the amino acid is in the
mobile phase, the further up the paper it
moves / the distance an amino acid moves
up the paper depends on its relative
solubility in the mobile and stationary
phases.
[1]
Total = 17
Answers to end-of-chapter questions: Chapter 29

4 a Element
Percentage
Mass in 100g
Number of moles
Relative number of
atoms

carbon
62.1
62.1 g

hydrogen
10.3
10.3 g

oxygen
27.6
27.6 g

62.1
= 5.18
12.0

10.3
= 10.3
1.0

27.6
= 1.73
16.0

5.18
=3
1.73

10.3
=6
1.73

1.73
=1
1.73

empirical formula = C3H6O

b molecular mass is 58
empirical formula mass = molecular mass,
therefore the molecular formula = C3H6O
c i
H
O H
H

[1]

Element
Percentage
Mass in 100g
Number of
moles in 100g

[1]

C
HH

propanal
H

[1]

carbon
90.6
90.6 g

hydrogen
9.4
9.4 g

90.6
= 7.55
12.0

9.4
= 9.4
1.0

Relative
7.55
=1
number of
7.55
atoms
Whole
4
numbers

empirical formula = C4H5

b the m/e value for the penultimate peak on the mass

spectrum = 106
[1]
this is twice the empirical formula mass, so the
molecular formula is C8H10
[1]
c i
H
H
H
H

ii it is propanal
[1]
iii There are three peaks present in the
1
H NMR spectrum;
[1]
propanone has only one type of proton
[1]
and therefore it would have only one peak. [1]
d this is the peak for the CH3 protons;
[1]
it is split into a triplet because of the two
chemically different (non-equivalent) protons on
the adjacent carbon (by applying the n + 1 rule in
which n = 2)
[1]
Total = 12
5 a

propanone

[1]
[1]

[1]

ii

H H
[1 mark for each structure] [4]

[1]

This is because when chlorinated by

electrophilic aromatic substitution it forms
only the following compound:
Cl

[1]
[1]

C
H

9.4
= 1.25
7.55

Answers to end-of-chapter questions: Chapter 29

[1]

The other possible isomers form several

different compounds.
[1]
The 1H NMR spectrum shows two peaks
as C has only two different types of proton; [1]
the other possible isomers have larger
numbers of different types of proton.
[1]
d The peak at = 7 ppm
[1]
is the peak from the benzene ring protons;
[1]
the peak at = 2.3 ppm
[1]
corresponds to the CH3 protons.
[1]
Total = 17

AS and A Level Chemistry Cambridge University Press

6 a

Element
Percentage
Mass in 100g
Number of moles in 100g

carbon
77.8
77.8 g

hydrogen
7.41
7.41 g

oxygen
14.8
14.8 g

77.8
= 6.48
12.0

7.41
= 7.41
1.0

14.8
= 0.925
16.0

Relative number of atoms

6.48
=7
0.925

7.41
=8
0.925

0.925
=1
0.925

empirical formula = C7H8O

b The m/e value for the molecular-ion peak
is 108;
this corresponds to the mass of the empirical
formula,
so molecular formula = empirical formula
= C7H8O.
c i
H

H
H

[1]
[1]

[1]

[1]

d There are three peaks because of the three

chemically different types of proton in D:
[1]
the peak for five protons at = 7.3 ppm is
caused by the five benzene protons;
[1]
the peak given by two protons at = 4.6 ppm
is caused by the CH2 protons;
[1]
the peak at = 2.4 ppm is caused by the OH
proton.
[1]
Total = 17

C
H

H
H
H

C
H

H
H

ii

H
[1 mark for each structure] [5]
H


H
iii The relative area of the peak at = 7.3 ppm
is 5, so there are five protons on the benzene
ring; therefore D cannot be a di-substituted
compound.
The other mono-substituted compound
has only two types of proton
but the 1H NMR spectrum of D has three
peaks, corresponding to the three different
types of proton in D.

AS and A Level Chemistry Cambridge University Press

[1]

[1]
[1]
[1]

Answers to end-of-chapter questions: Chapter 29

7 a

Element
Percentage
Mass in 100g
Number of moles in 100g

carbon
69.8
69.8 g

hydrogen
11.6
11.6 g

oxygen
18.6
18.6 g

69.8
= 5.82
12.0

11.6
= 11.6
1.0

18.6
= 1.16
16.0

11.6
= 10
1.16

1.16
=1
1.16

Relative number of atoms 5.82

=5
1.16
empirical formula = C5H10O

[1]

b The m/e value for the molecular-ion peak is 86 so

its relative molecular mass is 86;
[1]
this is the same as the empirical formula mass, so
the molecular formula is also C5H10O.
[1]
c
H H H H
H H H
H

H
O

H
H

H
H

C
O

d It is an aldehyde, because of the positive

result from the silver mirror test.
e on the 1H NMR spectrum there is an
absorption at = 9.5 ppm, characteristic of
the aldehyde CHO proton;
it has only two distinct peaks and therefore
only two types of proton;
therefore E must be

H
C

H
H

O
H

C
O

H
H

H
H

H
H

H
H

[1]
[1]
[1]

H
H

[1]

H
H
C
O

H

[1]
There is no splitting of the peaks because there
are no adjacent carbons with chemically different
protons on them.
[1]
Total = 16

H
O
C

H
C

C
H

H
H

O
C

C
C

[1 mark for each structure] [7]

Answers to end-of-chapter questions: Chapter 29

AS and A Level Chemistry Cambridge University Press