NMR Spectroscopy QP

AQA Chemistry A-Level - NMR Spectroscopy QP PhysicsAndMathsTutor.
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Q1.
This question is about spectroscopy.
(a) Compound K has molecular formula C4H8O

Figure 1 shows the infrared spectrum of K.
Figure 1
Which functional group does K contain?
Tick (✓) one box.
Functional Group
alcohol alkene amine carbonyl nitrile
(1)
(b) Compound L has molecular formula C4H7NO

Figure 2 shows the infrared spectrum of L.
Figure 2
Page 1 of 13
AQA Chemistry A-Level - NMR Spectroscopy QP PhysicsAndMathsTutor.com
L reacts with H2 in the presence of a nickel catalyst to give compound M.
Suggest three ways in which the infrared spectrum of M is different from

the infrared spectrum of L.
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2 _________________________________________________________
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3 _________________________________________________________
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(3)
(c) Figure 3 shows the 1H NMR spectrum of Q, C3H7ClO
Figure 3
The table below shows the chemical shifts (δ values) and integration
values for each peak.
δ value / ppm 3.95 3.65 3.35
Integration
0.6 0.6 0.9
value
Deduce the structure of Q.
Explain your answer.
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(5)
(Total 9 marks)
Q2.
This question is about NMR spectroscopy.
(a) A compound is usually mixed with Si(CH3)4 and either CCl4 or CDCl3 before
recording the compound’s 1H NMR spectrum.
State why Si(CH3)4, CCl4 and CDCl3 are used in 1H NMR spectroscopy.
Explain how their properties make them suitable for use in 1H NMR
spectroscopy.
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(6)
Page 3 of 13
(b) Deduce the splitting pattern for each of the peaks given by the H atoms
labelled x, y and z in the 1H NMR spectrum of the compound shown.
x _____________________________________________
y _____________________________________________
z _____________________________________________
(3)
(c) Suggest why it is difficult to use Table B in the Data Booklet to predict the
chemical shift (δ value) for the peak given by the H atom labelled y.
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(1)
(d) Two isomers of CH3CHClCOCH(CH3)2 each have two singlet peaks only in
their 1H NMR spectra.
In both spectra the integration ratio for the two peaks is 2:9
Deduce the structures of these two isomers.
Isomer 1
Isomer 2
(2)
(Total 12 marks)
Page 4 of 13
Q3.
There are several isomers with the molecular formula C6H16N2
(a) One isomer is shown.
Give the number of peaks in the 13C NMR spectrum of this isomer.
State and explain the splitting pattern of the peak for the hydrogens
labelled a in its 1H NMR spectrum.
Number of 13C peaks

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Splitting pattern
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Explanation
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(3)
(b) Draw the structure of the isomer of C6H16N2 used to make nylon 6,6
(1)
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(c) Draw the structure of the isomer of C6H16N2 that contains two primary
amine groups and has only two peaks in its 13C NMR spectrum.
(1)
(d) Draw the structure of the isomer of C6H16N2 that contains two tertiary
amine groups and has only two peaks in its 13C NMR spectrum.
(1)
(Total 6 marks)
Q4.
How many peaks are there in the 13C NMR spectrum of 1,4-dimethylbenzene?
A 8
B 4
C 3
D 2
(Total 1 mark)
Page 6 of 13
Q5.
How many peaks does this compound have in its 13C spectrum?
A 5
B 6
C 7
D 8
(Total 1 mark)
Q6.
1H NMR, 13C NMR and infrared spectroscopy are used in organic chemistry to
distinguish between compounds and to identify them.
(a) Give the skeletal formula of the compound that is used as the standard
when recording a 13C NMR spectrum.
(1)
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(b) Four isomers of C6H12O2, P, Q, R and S, shown in Figure 1, were analysed

by
13C NMR spectrometry.
The 13C NMR spectra of three of these isomers are shown in Figure 2.
Use Table C in the Data Booklet to help you to identify which isomer
produces each spectrum.
Page 8 of 13
Write the letter of each isomer opposite its spectrum in Figure 2.
Figure 2
Page 9 of 13
(3)
(c) The infrared spectra shown in Figure 3 are those of three different isomers
of C6H12O2, isomers T, U and V.
Page 10 of 13
Identify the functional group(s) present in each isomer T, U and V of

C6H12O2 using Table A in the Data Booklet.
Explain your answer.
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Page 11 of 13
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(6)
(d) The integration values for the peaks in the 1H NMR spectrum of X, a
different isomer of C6H12O2, are given in the table below.
Chemical shift, δ/ppm 3.7 3.5 2.6 2.2 1.1
Integration value 0.6 0.6 0.6 0.9 0.9
Splitting pattern triplet quartet triplet singlet triplet
Deduce the simplest ratio of the relative numbers of protons in each

environment in compound X.
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(1)
(e) Use the data in the table above and Table B in the Data Booklet to help
you answer this question.
Deduce the part of the structure of X that causes the signal at δ= 3.5 and
the part of the structure at X that causes the signal at δ=2.2.
Explain the splitting patterns of these peaks.
Signal at δ= 3.5
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Signal at δ= 2.2
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(4)
Page 12 of 13
(f) Deduce the structure of compound X, C6H12O2
Use your answer from part (e) to help you.
You are not required to explain how you deduced the structure.
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(2)
(Total 17 marks)
Q7.
Which amine has only three peaks in its proton NMR spectrum?
A Methylamine
B Trimethylamine
C Diethylamine
D Propylamine
Page 13 of 13

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AQA Chemistry A-Level - NMR Spectroscopy QP PhysicsAndMathsTutor.

(a) Compound K has molecular formula C4H8O

Which functional group does K contain?

Tick (✓) one box.

alcohol alkene amine carbonyl nitrile

(b) Compound L has molecular formula C4H7NO

L reacts with H2 in the presence of a nickel catalyst to give compound M.

Suggest three ways in which the infrared spectrum of M is different from

(c) Figure 3 shows the 1H NMR spectrum of Q, C3H7ClO

δ value / ppm 3.95 3.65 3.35

Deduce the structure of Q.

Explain your answer.

Deduce the structures of these two isomers.

(a) One isomer is shown.

Number of 13C peaks

(b) Four isomers of C6H12O2, P, Q, R and S, shown in Figure 1, were analysed

Write the letter of each isomer opposite its spectrum in Figure 2.

Identify the functional group(s) present in each isomer T, U and V of

Explain your answer.

Chemical shift, δ/ppm 3.7 3.5 2.6 2.2 1.1

Integration value 0.6 0.6 0.6 0.9 0.9

Splitting pattern triplet quartet triplet singlet triplet

Deduce the simplest ratio of the relative numbers of protons in each

Explain the splitting patterns of these peaks.

(f) Deduce the structure of compound X, C6H12O2

Use your answer from part (e) to help you.

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