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NMR spectroscopy and combined techniques

Past-paper questions pack

Name
Class
Date set
Date due
Score/ 116

Questions are numbered; the mark schemes (the answer key) follow on separate pages so the question pages can be handed out alone. www.chemistryaleveltutor.com

OCR AS and A-level Chemistry past-paper questions since 2016 · 38 parts · mark schemes follow the questions · www.chemistryaleveltutor.com · Questions and mark schemes © OCR

1. June 2025 · Paper 2 · Q15 · 1 marks ·
15 Which compound(s) has/have three peaks in their 13C NMR spectrum?
OH
1
OH
OH
2
HO
HO OH
3
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
2. June 2025 · Paper 2 · Q23(a) · 4 marks ·
23 This question is about spectral analysis.
(a) Compound K, C4H10O, is refluxed with H2SO4 to form a mixture of compound L and
compound M.
The infrared spectrum of compound K is shown.
100
50
Transmittance
(%)
0
4000 3000 2000 1500 1000 500
Wavenumber / cm−1
Compound L and compound M are analysed using 13C NMR spectroscopy.
• The 13C NMR spectrum of compound L has 4 peaks.
• The 13C NMR spectrum of compound M has 2 peaks.
Suggest the functional group in compound K, showing your reasoning, and suggest possible
structures for compound K, compound L and compound M.
Functional group  ..............................................................
Reasoning  ........................................................................................................................................
Possible structure
K
L
M
[4]
3. June 2025 · Paper 2 · Q23(b) · 6 marks ·
(b)* An unknown organic compound N is analysed and produces the following results.
Elemental analysis by mass
C, 62.07%; H, 10.34%; O, 27.59%
Mass spectrum
100
80
60
Relative
intensity
40
20
0
10 20 30 40 50 60 70 80 90 100 110 120
m / z
Proton NMR spectrum
Expansion of multiplet
3
6
2
1
6 5 4 3 2 1 0
Chemical shift, δ / ppm
The numbers by the peaks are the relative peak areas.
Determine the structure of the compound N, showing all your reasoning.
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4. June 2025 · Paper 3 · Q1(b) · 3 marks ·
(b) This question looks at proton NMR spectra of dibromoalkanes.
Predict the following.
Compound Number of peaks CH2 splitting pattern(s)
BrCH2CH2Br
BrCH2CH2CH2Br
[3]
5. June 2024 · Paper 2 · Q14 · 1 marks ·
14 The structures of 3 compounds, 1, 2 and 3, are shown below.
Which compound(s) would produce a carbon-13 NMR spectrum with 2 peaks?
HO
OH
1 2 3
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
6. June 2024 · Paper 2 · Q24 · 6 marks ·
24* Analysis of an unknown organic compound J produces the following results.
Elemental analysis by mass of compound J
C, 80.60%; H, 7.46%; O, 11.94%
Mass spectrum of compound J
100
80
60
Relative
intensity
40
20
0
25 50 75 100 125
m / z
IR spectrum of compound J
100
Transmittance
(%) 50
0
4000 3000 2000 1500 1000 500
Wavenumber / cm−1
Proton NMR spectrum of compound J
5
3
1
1
10 8 6 4 2 0
Chemical shift, δ / ppm
The numbers by the peaks are the relative peak areas.
Determine the structure of compound J, showing all your reasoning. [6]
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7. June 2023 · Paper 2 · Q1 · 1 marks · AO1
1 Which compound is used for proton exchange in NMR spectroscopy?
A CCl4
B CDCl3
C D2O
D Si(CH3)4
Your answer
[1]
8. June 2023 · Paper 2 · Q9 · 1 marks · AO2
9 Which compound has the greatest number of peaks in its proton NMR spectrum?
O
A
O
Br
B Br
O O
C
HO OH
OH
D O
Your answer
[1]
9. June 2023 · Paper 2 · Q17(d) · 5 marks · AO2, 3
(d) There are 4 structural isomers of C4H10O that are alcohols.
A student predicts that these structural isomers could be distinguished using carbon-13 NMR
spectroscopy.
Explain whether the student is correct.
In your answer, show how the peaks in the carbon-13 NMR spectra are linked to the
structure of each alcohol isomer.
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10. June 2023 · Paper 2 · Q23 · 6 marks · AO1, 3
23* An unknown organic compound is analysed.
The results are shown below.
Addition of 2,4-DNP
No visible change
Elemental analysis by mass
C, 66.63%; H, 11.18%; O, 22.19%
Mass spectrum
Molecular ion peak at m / z = 144.0
IR spectrum
100
transmittance
(%) 50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
Proton NMR spectrum
The numbers by each peak are the relative peak areas.
9
2
3
2
5 4 3 2 1 0
chemical shift, δ / ppm
Use the information to identify the organic compound.
Show all your reasoning.
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11. June 2022 · Paper 2 · Q12 · 1 marks · AO2
12 Which compound produces two triplets in its 1H NMR spectrum?
A CH3CH2COOCH2CH3
B CH3CH2COCH2CH3
C HOOCCH2CH2COOH
D HOOCCH2CH2CH2COOH
Your answer
[1]
12. June 2022 · Paper 2 · Q15 · 1 marks · AO2
15 Which isomer(s) of C5H12O has/have 4 peaks in its/their 13C NMR spectrum?
1 3-methylbutan-2-ol
2 2-methylbutan-2-ol
3 2-methylbutan-1-ol
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
13. June 2022 · Paper 2 · Q16(b)(v) · 4 marks · AO2
(v) Compounds D and E are two more structural isomers of C6H12.
Compounds D and E do not show stereoisomerism.
Table 16.1 shows NMR and infrared (IR) spectral data for D and E.
Number of peaks in Number of peaks in IR peak at
1H NMR spectrum 13C NMR spectrum 1620–1680 cm–1
D 1 1 No
E 1 2 Yes
Table 16.1
Draw the structures of D and E and explain how the spectral data in Table 16.1
provides evidence for the structures.
D E
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14. June 2022 · Paper 2 · Q18(c) · 4 marks · AO3
(c) The organic compound H contains carbon, hydrogen and oxygen only and has an Mr of
114.0.
Compound H has two carbonyl groups and no other functional groups.
The 1H NMR spectrum of organic compound H is shown below.
Expansion of multiplet
centred at δ = 2.9 ppm
3
6
1
4 3 2 1 0
chemical shift, δ / ppm
The numbers by the peaks are the relative peak areas.
Analyse the spectrum to suggest a possible structure for compound H.
Show all your reasoning.
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Compound H
[4]
15. June 2022 · Paper 2 · Q20(a)(ii) · 3 marks · AO3
(ii) A student thought that 13C NMR spectroscopy could be used to distinguish between
compounds J, K and L.
Explain, with reasoning, whether the student is correct.
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16. June 2022 · Paper 3 · Q1(c)(i) · 2 marks · AO1
(c) The structure of an organic compound is shown below.
The protons are in four different environments, which are labelled 1–4.
2 3
1
CH2 CH2 O
H3C C C
O H
4
(i) Fill in the table to predict the splitting patterns in the proton NMR spectrum of the
organic compound.
Proton environment Splitting pattern
1
2
3
4
[2]
17. June 2022 · Paper 3 · Q1(c)(ii) · 2 marks · AO3
(ii) The table shows the chemical shifts for the peaks in the proton NMR spectrum at
proton environments 2 and 3.
Proton environment 2 3
Chemical shift, δ 2.5 ppm 3.6 ppm
Suggest why the peaks for proton environments 2 and 3 have the chemical shifts which
are shown in the table.
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18. November 2021 · Paper 2 · Q13 · 1 marks ·
13 Which compound(s) has/have four peaks in a 13C NMR spectrum?
O
1
2
O
3
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
19. November 2021 · Paper 2 · Q20(b)(ii) · 6 marks · AO1, 3
(ii) The pure sample of C is analysed to give the following results.
Percentage composition by mass: C, 31.44%; H, 1.31%; N, 18.34%; O, 48.91%.
The mass spectrum of C shows a molecular ion peak at m /z = 229.0
The 13C NMR spectrum of C is shown below.
160 140 120 100 80 60 40 20 0
chemical shift, δ / ppm
The table shows directing effects for different groups in the electrophilic substitution of
aromatic compounds.
Directing effect 2- and 4- directing 3-directing
–OH –NO2
Group
–NH2
Analyse all the information to suggest the structure for C.
Show all your reasoning.
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compound C
[6]
20. November 2021 · Paper 2 · Q21 · 6 marks · AO3
21* Compounds D, E and F are isomers with the molecular formula C5H10O.
One of the compounds is alicyclic.
A student carries out test-tube tests on the compounds.
The observations are shown below.
Compound 2,4-DNP H+/Cr2O7 2–, reflux Bromine water
D No change Green solution No colour change
Orange
E No colour change No colour change
precipitate
Orange
F No colour change No colour change
precipitate
13C NMR spectrum of D Compound D has 3 peaks at δ / ppm: 24, 36, 73.
1H NMR spectra of E and F The integration data has been omitted.
Compound E
3 2 1 0
chemical shift, δ / ppm
Compound F
Expansion of multiplet
3 2 1 0
chemical shift, δ / ppm
Analyse the observations and results to identify the structures of D, E and F.
Explain your reasoning. [6]
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21. November 2020 · Paper 2 · Q8 · 1 marks · AO2
8 Which isomer of C6H12O2 produces the smallest number of peaks in its 13C NMR spectrum?
O
A
OH
O
B
O
O
C
OH
O
D
OH
Your answer
[1]
22. November 2020 · Paper 2 · Q17(c)(i) · 2 marks · AO3
(c) An organic chemist is investigating compound D for possible use as a medicine.
The chemist proposes a synthesis of compound D from compound C.
O
HN
compound C compound D
(i) Predict the number of peaks in the 13C NMR spectra of compounds C and D.
Compound C Compound D
Number of peaks
....................... .......................
[2]
23. November 2020 · Paper 2 · Q22(a) · 2 marks · AO1
22 An organic compound I is analysed, using a combination of techniques. The analytical data is
shown below.
Elemental analysis by mass
C, 56.69%; H, 7.09%; N, 11.02%; O, 25.20%
Mass spectrum
Molecular ion peak at m / z = 127.0
IR spectrum
© SDBS, National Institute of Advanced Industrial Science and Technology.
Proton NMR spectrum
3 3
2
1
5 4 3 2 1 0
Chemical shift, d / ppm
(a) Explain the use of two deuterated compounds in NMR spectroscopy.
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24. November 2020 · Paper 2 · Q22(b) · 6 marks · AO3
(b)* Determine the structure of compound I, showing all your reasoning. [6]
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25. November 2020 · Paper 3 · Q1(b)(ii) · 6 marks · AO2, 3
(ii) Amine A is a liquid at room temperature and pressure.
When vaporised, 0.202 g of the amine produces 72.0 cm3 of gas at 1.00 × 105 Pa and
100 °C. The 13C NMR spectrum of amine A has 3 peaks.
Determine the molecular formula of A and suggest a possible structure for amine A.
Molecular formula of A  ...............................................................
Structure of A
[6]
26. June 2019 · Paper 2 · Q10 · 1 marks · AO2
10 Which compound shows 4 peaks in its carbon-13 NMR spectrum?
A
B
C
D
Your answer
[1]
27. June 2019 · Paper 2 · Q12 · 1 marks · AO2
12 A compound produces the 13C NMR spectrum below.
80 70 60 50 40 30 20 10 0
chemical shift, d / ppm
Which compound could have produced this spectrum?
A Propane
B 2-Methylbutane
C 2-Methylpropan-1-ol
D 2-Methylpropan-2-ol
Your answer
[1]
28. June 2019 · Paper 2 · Q18(b) · 4 marks · AO3
(b) The protons in ester A are in four different environments, labelled 1– 4 on the structure below.
1 O 3
4
CH2 C CH2
Br CH2 O CH3
2
Complete the table to predict the proton NMR spectrum of ester A.
Proton environment Chemical shift Splitting pattern
1
2
3
4
[4]
29. June 2019 · Paper 2 · Q18(c) · 1 marks · AO3
(c) Compound B is a structural isomer of ester A.
• Compound B reacts with aqueous sodium carbonate.
• The 13C NMR spectrum of B has 4 peaks.
Draw a possible structure for compound B.
[1]
30. June 2019 · Paper 2 · Q21 · 6 marks ·
21* Analysis of an unknown organic compound produced the following results.
Elemental analysis by mass
C: 73.17%; H: 7.32%; O: 19.51%
Mass spectrum
Molecular ion peak at m / z = 164.0
Infrared spectrum
100
Transmittance
(%) 50
0
4000 3000 2000 1500 1000 500
Wavenumber / cm–1
1H NMR spectrum in D2O
3
4 3
1
8 7 6 5 4 3 2 1 0
Chemical shift, d / ppm
The numbers by the peaks are the relative peak areas.
Use the results to suggest one possible structure for the unknown compound.
Show all your reasoning. [6]
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31. June 2019 · Paper 3 · Q4(a)(ii) · 1 marks · AO2
(ii) Predict the number of peaks in a 13C NMR spectrum of chloroxylenol.
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32. June 2018 · Paper 2 · Q1 · 1 marks ·
1 Which compound is used as a standard for NMR chemical shift measurements?
A Si(CH3)4
B CDCl 3
C D2O
D CCl 4
Your answer
[1]
33. June 2018 · Paper 2 · Q6 · 1 marks ·
6 What is the number of peaks in the 1H NMR spectrum of HOOCCH2CHOHCH2COOH?
A 3
B 4
C 5
D 6
Your answer
[1]
34. June 2018 · Paper 2 · Q18(a)(i) · 3 marks ·
18 This question is about aromatic compounds.
(a) Phenol undergoes nitration more readily than benzene.
(i) A student carries out the nitration of phenol with dilute nitric acid to produce 2-nitrophenol
and 4-nitrophenol.
A small amount of 3-nitrophenol is also produced.
OH
OH OH
NO2
NO2
NO2
2-nitrophenol 3-nitrophenol 4-nitrophenol
The student thought that 13C NMR spectroscopy could be used to distinguish between
these three nitrophenols.
Explain whether the student is correct.
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35. June 2018 · Paper 2 · Q22(d) · 6 marks ·
(d)* A scientist is researching compounds that might be suitable as fuel additives.
One of the compounds gives the analytical results below.
Elemental analysis by mass:
C: 54.54%; H: 9.10%; O: 36.36%
Mass spectrum:
Molecular ion peak at m/z = 132.0
1H NMR spectrum in D2O
6
3
1
5 4 3 2 1 0
chemical shift,  / ppm
The numbers by the peaks are the relative peak areas.
When the spectrum is run without D2O, there are two additional peaks with the same relative
peak areas at 11.0 ppm and 3.6 ppm.
Use the information provided to suggest a structure for the compound.
Show all your reasoning. [6]
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36. June 2017 · Paper 2 · Q11 · 1 marks ·
11 The compound below is analysed by 1H NMR spectroscopy.
O O
HO OH
How many peaks are observed in the 1H NMR spectrum?
A 5
B 4
C 3
D 2
Your answer
[1]
37. June 2017 · Paper 2 · Q20(c) · 3 marks ·
(c) The carbon-13 NMR spectrum of the compound is shown below.
200 180 160 140 120 100 80 60 40 20 0
chemical shift,   / ppm δ
Using the spectrum and the results from (a) and (b), determine the structure of the compound.
Explain your reasoning.
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Structure of compound
[3]
38. June 2017 · Paper 2 · Q21 · 6 marks ·
21* Compound L is an organic compound containing carbon, hydrogen and oxygen only.
The 1H NMR spectrum of compound L is shown below.
The numbers by the peaks are the relative peak areas.
9
3
2
2
5 4 3 2 1 0
chemical shift,   / ppm δ
Compound L is refluxed with aqueous hydrochloric acid, forming two organic compounds M
and N. The infrared spectra of M and N are shown below.
Infrared spectrum of M
Item removed due to third party copyright restrictions.
Infrared spectrum of N
100
transmittance
(%) 50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
Use the information provided to suggest a structure for compound L.
Show all of your reasoning.
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Mark schemes

1. June 2025 · Paper 2 · Q15
Mark scheme June 2025 Paper 2 Q15
2. June 2025 · Paper 2 · Q23(a)
Mark scheme June 2025 Paper 2 Q23(a)
3. June 2025 · Paper 2 · Q23(b)
Mark scheme June 2025 Paper 2 Q23(b)
4. June 2025 · Paper 3 · Q1(b)
Mark scheme June 2025 Paper 3 Q1(b)
5. June 2024 · Paper 2 · Q14
Mark scheme June 2024 Paper 2 Q14
6. June 2024 · Paper 2 · Q24
Mark scheme June 2024 Paper 2 Q24
7. June 2023 · Paper 2 · Q1
Mark scheme June 2023 Paper 2 Q1
8. June 2023 · Paper 2 · Q9
Mark scheme June 2023 Paper 2 Q9
9. June 2023 · Paper 2 · Q17(d)
Mark scheme June 2023 Paper 2 Q17(d)
10. June 2023 · Paper 2 · Q23
Mark scheme June 2023 Paper 2 Q23
11. June 2022 · Paper 2 · Q12
Mark scheme June 2022 Paper 2 Q12
12. June 2022 · Paper 2 · Q15
Mark scheme June 2022 Paper 2 Q15
13. June 2022 · Paper 2 · Q16(b)(v)
Mark scheme June 2022 Paper 2 Q16(b)(v)
14. June 2022 · Paper 2 · Q18(c)
Mark scheme June 2022 Paper 2 Q18(c)
15. June 2022 · Paper 2 · Q20(a)(ii)
Mark scheme June 2022 Paper 2 Q20(a)(ii)
16. June 2022 · Paper 3 · Q1(c)(i)
Mark scheme June 2022 Paper 3 Q1(c)(i)
17. June 2022 · Paper 3 · Q1(c)(ii)
Mark scheme June 2022 Paper 3 Q1(c)(ii)
18. November 2021 · Paper 2 · Q13
Mark scheme November 2021 Paper 2 Q13
19. November 2021 · Paper 2 · Q20(b)(ii)
Mark scheme November 2021 Paper 2 Q20(b)(ii)
20. November 2021 · Paper 2 · Q21
Mark scheme November 2021 Paper 2 Q21
21. November 2020 · Paper 2 · Q8
Mark scheme November 2020 Paper 2 Q8
22. November 2020 · Paper 2 · Q17(c)(i)
Mark scheme November 2020 Paper 2 Q17(c)(i)
23. November 2020 · Paper 2 · Q22(a)
Mark scheme November 2020 Paper 2 Q22(a)
24. November 2020 · Paper 2 · Q22(b)
Mark scheme November 2020 Paper 2 Q22(b)
25. November 2020 · Paper 3 · Q1(b)(ii)
Mark scheme November 2020 Paper 3 Q1(b)(ii)
26. June 2019 · Paper 2 · Q10
Mark scheme June 2019 Paper 2 Q10
27. June 2019 · Paper 2 · Q12
Mark scheme June 2019 Paper 2 Q12
28. June 2019 · Paper 2 · Q18(b)
Mark scheme June 2019 Paper 2 Q18(b)
29. June 2019 · Paper 2 · Q18(c)
Mark scheme June 2019 Paper 2 Q18(c)
30. June 2019 · Paper 2 · Q21
Mark scheme June 2019 Paper 2 Q21
31. June 2019 · Paper 3 · Q4(a)(ii)
Mark scheme June 2019 Paper 3 Q4(a)(ii)
32. June 2018 · Paper 2 · Q1
Mark scheme June 2018 Paper 2 Q1
33. June 2018 · Paper 2 · Q6
Mark scheme June 2018 Paper 2 Q6
34. June 2018 · Paper 2 · Q18(a)(i)
Mark scheme June 2018 Paper 2 Q18(a)(i)
35. June 2018 · Paper 2 · Q22(d)
Mark scheme June 2018 Paper 2 Q22(d)
36. June 2017 · Paper 2 · Q11
Mark scheme June 2017 Paper 2 Q11
37. June 2017 · Paper 2 · Q20(c)
Mark scheme June 2017 Paper 2 Q20(c)
38. June 2017 · Paper 2 · Q21
Mark scheme June 2017 Paper 2 Q21