Cambridge International AS & A Level

10: Analysis – Topic questions

The questions in this document have been compiled from a number of past papers, as indicated in the table
below.

Use these questions to formatively assess your learners’ understanding of this topic.

Question Year Series Paper number

9 2017 March 42
6 2017 November 43
8 2017 November 42

The mark scheme for each question is provided at the end of the document.

You can find the complete question papers and the complete mark schemes (with additional notes where
available) on the School Support Hub at www.cambridgeinternational.org/support

10: Analysis - Topic questions UCLES © 2018 1

 9 This question is about compound T, CxHyOz.

(a) Part of the mass spectrum of T is shown.

The peak heights of the M and M+1 peaks are 33.9 and 3.4 respectively.

100

80

60
relative
intensity
40

20

0
50 75 100 125 150
m/e

(i) Calculate x, the number of carbon atoms present in T.

x = .............................. [2]

(ii) Deduce the molecular formula of T.

....................................................................................................................................... [1]

(iii) The mass spectrum has a peak at m / e = 119.

Identify the fragment lost from T to produce this peak.

....................................................................................................................................... [1]

10: Analysis - Topic questions UCLES © 2018 2

 (b) The infra-red spectrum of T is shown.

100

transmittance
50

V W
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Identify the type of bond responsible for each of the peaks V and W.
Use the Data Booklet to help you.

V .............................. W .............................. [1]

(c) The proton NMR spectrum of T in CDCl 3 is shown.

3H 3H

4H

11 10 9 8 7 6 5 4 3 2 1 0
δ / ppm

(i) Complete the table for the proton NMR spectrum of T.

Use the Data Booklet to help you.

δ / ppm type of proton

3.9

7.2–7.9
[1]

10: Analysis - Topic questions UCLES © 2018 3

 (ii) The peak at δ = 2.4 ppm is due to a proton attached to a saturated carbon atom.

State the two possible types of proton.

1. .........................................................................................................................................

2. .........................................................................................................................................
[1]

(iii) Adding D2O to T does not change its proton NMR spectrum.

What does this tell you about the functional groups present in T?

....................................................................................................................................... [1]

(d) Use the information to draw two possible structures of T which are functional group isomers of
each other.

[2]

[Total: 10]

10: Analysis - Topic questions UCLES © 2018 4

 6 (a) 4-nitromethylbenzene can be prepared via an electrophilic substitution reaction as shown.

CH3 CH3 CH3

conc. HNO3
conc. H2SO4

H NO2 NO2

methylbenzene intermediate T 4-nitromethylbenzene

(i) This reaction also forms an isomer of 4-nitromethylbenzene as a by-product.

Draw the structure of this by-product.

[1]

(ii) Write an equation for the reaction between HNO3 and H2SO4 that forms the electrophile for
this reaction.

....................................................................................................................................... [1]

(iii) Describe how the structure and bonding of the six-membered ring in intermediate T
differs from that in methylbenzene.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [3]

10: Analysis - Topic questions UCLES © 2018 5

 (b) Benzocaine is used as a local anaesthetic. It can be synthesised from 4-nitromethylbenzene
by the route shown.

CH3 CH3 CH3

step 1 step 2

NO2 NH2 NHCOCH3

4-nitromethylbenzene
step 3

CO2CH2CH3 CO2H CO2H

step 5 step 4

NH2 NH2 NHCOCH3

benzocaine W

(i) Give the systematic name of compound W.

....................................................................................................................................... [1]

(ii) Suggest the reagents and conditions for steps 1– 5.

step 1 ..................................................................................................................................

step 2 ..................................................................................................................................

step 3 ..................................................................................................................................

step 4 ..................................................................................................................................

step 5 ..................................................................................................................................
[6]

(c) Suggest how the basicity of benzocaine would compare to that of ethylamine.
Explain your answer.

....................................................................................................................................................

....................................................................................................................................................

.............................................................................................................................................. [2]

10: Analysis - Topic questions UCLES © 2018 6

 (d) A sample of benzocaine, shown below, was analysed by proton NMR and carbon-13 NMR
spectroscopy.

(i) Predict the number of peaks that would be seen in the carbon-13 NMR spectrum.

....................................................................................................................................... [1]

(ii) Benzocaine was dissolved in CDCl 3 and the proton NMR spectrum of this solution was
recorded.

CO2CH2CH3

NH2

benzocaine

8 7
δ / ppm

Suggest why CDCl 3 and not CHCl 3 is used as the solvent when obtaining a proton NMR
spectrum.

.............................................................................................................................................

....................................................................................................................................... [1]

(iii) Use the Data Booklet and the spectrum in (d)(ii) to complete the table for the proton
NMR spectrum of benzocaine. The actual chemical shifts, δ, for the four absorptions have
been added.

group responsible number of 1H atoms

δ / ppm splitting pattern
for the peak responsible for the peak

1.2

3.5

5.5

7.1–7.4 multiplet
[4]

(iv) Explain the splitting pattern for the absorption at δ1.2 ppm.

.............................................................................................................................................

....................................................................................................................................... [1]

10: Analysis - Topic questions UCLES © 2018 7

 (v) The proton NMR spectrum of benzocaine dissolved in D2O was recorded.

Suggest how this spectrum would differ from the spectrum in (d)(ii).
Explain your answer.

.............................................................................................................................................

....................................................................................................................................... [1]

(e) Benzocaine can also be used to synthesise the dyestuff S by the following route.

CO2CH2CH3

step 1

NH2
R
benzocaine

step 2 NaOH(aq), OH

phenol

(i) Suggest the reagents used for step 1.

....................................................................................................................................... [1]

(ii) Suggest structures for compounds R and S and draw them in the boxes. [2]

[Total: 25]

10: Analysis - Topic questions UCLES © 2018 8

 8 (a) Compound A can be produced from a plant hormone.

A
OH
O HO O

(i) Compound A shows optical and geometrical isomerism.

On the structure of A above,

● draw a line through the bond(s) that give rise to geometrical isomerism,
● circle all chiral carbon atoms.
[2]

(ii) Give the names of four functional groups present in A.

.............................................................................................................................................

....................................................................................................................................... [2]

(iii) A molecule of A has 17 carbon atoms.

State the number of carbon atoms that are sp, sp2 and sp3 hybridised in A.

sp carbons = .................... sp2 carbons = .................... sp3 carbons = ....................

[1]

(iv) When A is reacted with an excess of hot, concentrated manganate(VII) ions, a mixture of
three organic compounds is formed.

A X and Y and Z
(C10H14O7) (C3H4O3) (C4H6O3)

Suggest the structures of Y and Z.

Y Z
(C3H4O3) (C4H6O3)

[2]

10: Analysis - Topic questions UCLES © 2018 9

 (b) A mixture of three different compounds, J, K and L, was analysed by thin layer chromatography
using a polar stationary phase and a non-polar mobile phase. The three compounds all have
similar molecular masses. The resulting chromatogram is shown.

solvent front

mixture

(i) Identify which spot corresponds to each compound.

compound spot

J CH3COCO2H

K HO2CCO2H

L CH3CH2COCH2CH3
[1]

(ii) Explain your answers to (b)(i).

..............................................................................................................................................

........................................................................................................................................ [1]

(iii) What is meant by the term Rf value?

..............................................................................................................................................

........................................................................................................................................ [1]

[Total: 10]

10: Analysis - Topic questions UCLES © 2018 10

 Question Answer Marks
9 (a) (i) n = 100 × (M+1)/(1.1 × M) = 100 × 3.4/(1.1 × 33.9) = 9.1 1

hence 9 carbons atoms 1

9 (a) (ii) C9H10O2 1

9 (a) (iii) (150 – 119 = 31), hence fragment is CH3O 1

9 (b) V is C=O AND W is C–O 1

9 (c) (i) δ 3.9 is CH or alkyl / CH3 next to oxygen AND δ 7.2–7.9 is CH / aryl 1
hydrogens

9 (c) (ii) alkyl H next to C=O AND alkyl H next to aryl ring 1

9 (c) (iii) none of the functional groups in T contains a labile proton / T does not 1
contain –OH or –NH groups.
9 (d) 2

Total: 10

Question Answer Marks

6 (a) (i) 1

6 (a) (ii) HNO3 + 2H2SO4 → H3O+ + NO2+ + 2HSO4– 1

6 (a) (iii) any three from: 3

Point 1: bonds / electrons are partially delocalised in T
or delocalised / π system / π bonding extends over only five
carbons
Point 2: four π-electrons in the (delocalised system of T)
or methylbenzene has (two) more π-electrons / (two) more
delocalised electrons
Point 3: contains a carbon that is sp3 hybridised in T
or (all the) carbons are sp2 hybridised in methylbenzene
Point 4: one carbon has a bond angle of 109.5° / tetrahedral (in T)
or (C-C) bond strengths / lengths are not all the same
or not all the bond angles are 120° (in T)
6 (b) (i) 4-aminobenzoic acid 1

step 5 substitution / hydrolysis 1

10: Analysis - Topic questions UCLES © 2018 11

 Question Answer Marks
4 (b) (iii) step 1 Sn + HCl 1

concentrated / reflux / heat 1

step 2 CH3COCl 1

step 3 KMnO4 / manganate(VII) / MnO4– (acidified / alkaline) and heat 1

step 4 aqueous HCl and heat 1

step 5 ethanol, H2SO4, concentrated / reflux / heat 1

6 (c) (benzocaine) is less (basic than ethylamine) AND 2

lone pair (on N) is less available to accept a proton / H+

since (lone pair on N) is delocalised over the ring

or phenyl ring is electron withdrawing group

OR
ethylamine is more basic (than benzocaine) AND
lone pair (on N) is more available to accept a proton / H+

since ethyl / alkyl group is electron-donating group

6 (d) (i) 7 peaks 1

6 (d) (ii) CDCl3 will produce no signal in the spectrum 1

or CHCl3 would produce a signal / would be detected
6 (d) (iii) 4
number of H
group
atoms
δ/ppm responsible for splitting pattern
responsible for
the peak
the peak
1.2 CH(3) 3 triplet
3.5 CH(2)O 2 quartet
5.5 NH2 2 singlet (broad)
7.1–7.4 H attached to 4 multiplet
aromatic /
benzene ring
fmdos[
6 (d) (iv) neighbouring / adjacent carbon atom has two protons / H (attached to it) 1
or there is an adjacent CH2(O) group
6 (d) (v) peak at 5.5 / NH2 peak will disappear 1
and
NH2 / protons exchange / swap with deuterium
6 (e) (i) NaNO2 + HCl or HNO2 1

10: Analysis - Topic questions UCLES © 2018 12

 Question Answer Marks
6 (e) (i)

structure of diazonium salt R 1

structure of azo dye S 1

Total: 25

Question Answer Marks

8 (a) (i) 2

circle or asterisk on correct C atom only [1]

lines through the two correct bonds only [1]

8 (a) (ii) ketone, (tertiary) alcohol, alkene, carboxylic acid 2

two for each mark
8 (a) (iii) sp carbons = 0 sp2 carbons = 8 sp3 carbons = 9 1

8 (a) (iv) 2

10: Analysis - Topic questions UCLES © 2018 13

 Question Answer Marks
8 (b) (i) 1

compound spot

J 2

K 3

L 1

nria[wd

8 (b) (ii) The more polar the compound and stronger attractive forces to the 1
(polar) stationary phase
ora: less polar compound and weaker attractive forces to the (polar)
stationary phase

8 (b) (iii) Rf = retardation factor or retention factor or 1

Rf =distance moved by compound from baseline over distance travelled
by solvent front

Total: 10
Notes about the mark scheme are available separately.

10: Analysis - Topic questions UCLES © 2018 14