OCR

A-Level
CHEMISTRY
Core Organic Chemistry
Analytical Techniques (IR & MS) 1

Time allowed
71 minutes

QUESTION PAPER

Score Percentage

/59 %
4.1 | CELL BIOLOGY | QUESTION PAPER 1 1
1 L, M, N and P are straight-chain organic compounds containing C, H and O only.

The flowchart shows reactions involving these compounds.

elimination of H2O polymer P

L N Mr ~ 10,000

H+/Cr2O72– reflux

dicarboxylic acid, M
Analysis of compound L shows the following.
• Percentage composition by mass: C, 40.00%; H, 6.67%; O, 53.33%.
• Relative molecular mass of 90.0.
• The infrared spectrum below.

IR spectrum of L
100
transmittance (%)

50

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

(a) Calculate the empirical and molecular formulae of compound L.

Show your working.

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 (b) Analyse the information and spectrum to determine the structures of L and M.

Include an equation for the reaction of L to form M.

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(c) Determine the structures of compounds N and P.

Estimate the number of repeat units in polymer P and write the equation for the formation of P
from N.

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[Total: 12]

PhysicsAndMathsTutor.com
2 (a) Compound B, CxHyO, can be oxidised to form a ketone
C.
0.035 mol of B has a mass of 2.59 g.

Compound B reacts with compound D, C3H6O2, in the presence of an acid catalyst to form
two compounds E and F.

• Calculate the molar mass of compound B.

• Give the structures of compounds B, C, D, E and F.

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 (b) Compound G is a branched-chain organic compound that does not have E and Z isomers.
Elemental analysis of compound G gave the following percentage composition by mass:
C, 55.8%; H, 7.0%; O, 37.2%.
The mass spectrum and infrared spectrum of compound G are shown below.

Mass spectrum

100

X
80

60
relative
intensity
40

20 Y

0
10 20 30 40 50 60 70 80 90 100
m /z

Infrared spectrum

100

transmittance
(%)
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
 • Calculate the empirical and molecular formulae for compound G.

• Write the formulae for the particles responsible for peak X and peak Y in the mass
spectrum.

• Draw the structure of compound G.

Explain fully how you arrive at a structure for compound G using all the evidence provided.

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[Total: 13]
3 Mass spectrometry and infrared spectroscopy are used in analysis.

(a) The element sulfur exists as molecules, Sn.

The mass spectrum that would be given by a sample of sulfur is shown below.
All the sulfur atoms are the same isotope.

abundance

32 64 96 128 160 192 224 256

m /z

(i) State the m/z value of the molecular ion.

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(ii) Suggest the formula for a molecule of sulfur.

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(iii) What is the formula for the fragment ion with m/z = 128?

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PhysicsAndMathsTutor.com
 (b) A sample of an element, L is analysed using mass spectrometry.
The mass spectrum is shown below.

40
33% 34%
30
25%
percentage
abundance
20
(%)

10 8%

0
194 195 196 198

m /z

Calculate the relative atomic mass of L.

Give your answer to one decimal place.

relative atomic mass of L = .......................................................... [2]

(c) Give an everyday use for infrared spectroscopy.

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PhysicsAndMathsTutor.com
 (d) The solvent, M, is an organic compound used in paints. The solvent M was analysed.

M has a relative molecular mass of 72.0.

The percentage composition by mass of M is C, 66.7%; H, 11.1%; O, 22.2%.

The infrared spectrum of M is shown below.

100

transmittance
(%)
50

0
4000 3000 2000 1500 1000 500

wavenumber / cm–1

The analysis produces several possible organic structures.

Suggest, with reasons, two possible structures for M.

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[Total: 11]

PhysicsAndMathsTutor.com
4 Compound X and compound Y react together to make an ester Z. Samples of X and Y were
analysed by a research chemist. A summary of the chemist’s results are shown below.
Analysis of compound X
type of analysis evidence
absorption at 1720 cm–1 and a very broad
infrared spectroscopy
absorption between 2500 and 3300 cm–1
percentage composition by mass C, 48.65%; H, 8.11%; O, 43.24%
mass spectrometry molecular ion peak at m/z = 74.0

Analysis of compound Y

infrared spectrum of Y

100

80

transmittance
(%) 60

40

20

mass spectrum of Y 4000 3500 3000 2500 2000 1500 1000 500
–1
wavenumber / cm
100

80

relative 60
abundance
(%)
40

20

0.0
10 20 30 40 50

m/z
Use this information to suggest the identity of compound X, compound Y and ester Z.

In your answer you should make clear how your explanation is linked to the evidence.

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[Total:10]
5 Infrared spectroscopy and mass spectrometry are used to identify substances.

(a) Police use breathalysers to detect ethanol in the breath of drivers.

(i) Some modern breathalysers use infrared spectroscopy.

Suggest two characteristic infrared absorptions that could be used to identify the
presence of ethanol vapour.

1 ……………………. cm–1

2 ……………………. cm–1 [2]

(ii) Some older breathalysers used the redox reaction between acidified dichromate(VI) ions
and ethanol. A colour change was seen which indicated the presence of ethanol in the
breath.

What is the colour change that would be seen in this breathalyser if ethanol was present
in the breath?

……………………………….. to ……………………………….. [1]

(iii) Give an equation to show the reaction between acidified dichromate(VI) ions and
ethanol.

Use [O] to represent the acidified dichromate(VI) ions, the oxidising agent.

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(b) Infrared spectroscopy and mass spectrometry are used in the search for organic molecules in
outer space.

Compound A has been analysed by infrared spectroscopy.

100

80

transmittance
(%) 60

40

20

4000 3500 3000 2500 2000 1500 1000 500

wavenumber / cm –1

The mass spectrum of compound A is shown below.

100

80

relative 60
abundance
(%)
40

20

0.0
0 10 20 30 40 50 60
m/z
 (i) A research chemist concludes that compound A is a hydrocarbon.

What evidence is there to support this conclusion?

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(ii) How does the mass spectrum confirm that compound A has a molecular formula of
C4H10?

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(iii) Draw the structural isomers of C4H10.

[1]

(iv) Identify the fragment ions that give rise to the following peaks in the mass spectrum.

m/z 15 is …………………….

m/z 29 is …………………….

m/z 43 is ……………………. [3]

(v) Use your answer to part (iv) to identify which of the isomers in part (iii) is compound A.
Explain your reasoning.

[1]

[Total: 13]
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