NATIONAL QUALIFICATIONS CURRICULUM SUPPORT

Chemistry
Proton (1H) NMR Spectroscopy

Learners Workbook
Answers

[REVISED ADVANCED HIGHER]

 The Scottish Qualifications Authority regularly
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Acknowledgement
The publisher gratefully acknowledges permission to use the following sources: link to video
clip from http://www.le.ac.uk/spectraschool/, 10 spectra graphs both The Royal Society of
Chemistrys Spectra School website; adapted diagram showing nuclei as compass needles,
diagram showing external magnetic field, image of low and high resolution spectra all Jim
Clark http://www.chemguide.co.uk.

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2 PROTON (1H) NMR SPECTROSCOPY (AH, CHEMISTRY)

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Contents

Proton environments 4

Assigning peaks 6

Drawing spectra 7

Analysing spectra 9

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Proton environments

For the examples below:

(a) draw the full structural formula

(b) circle the different proton environments.

1. Propan-1-ol

H H H
H C C C O
H H H H

2. Propan-2-ol

H
H O H
H C C C H
H H H

3. Butane

H H H H
H C C C C H
H H H H

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4. But-2-ene

H H
H C C C C H
H H H H

5. Methyl benzene

H
H C H

H C H
C C
C C
H C H
H

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Assigning peaks

Use the 1 H NMR correlation table in the data book to predict the chemical
shift of the protons in the examples in the above question.

The shifts are given as a range in the data book. Learners should be
encouraged to quote only one value for shift in this exercise and it should be
within the range given below.

1. Propan-1-ol

Group Chemical shift (ppm)

CH 3 1.2
CH2 1.50.9
(left of CH3 due to proximity to OH)
CH2 3.93.5
OH 5.01.0

2. Propan-2-ol

Group Chemical shift (ppm)

CH3 1.50.9
CH 3.93.5
OH 5.01.0

3. Butane

Group Chemical shift (ppm)

CH3 1.50.9
CH2 1.50.9

4. But-2-ene

Group Chemical shift (ppm)

CH3 2.61.6
CH 6.04.5

5. Methyl benzene

Group Chemical shift (ppm)

CH3 3.02.3
CH 8.06.6

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Drawing spectra

For the examples above, draw the low resolution NMR spectrum you would
expect to see. Remember to draw in the appropriate peak heights you can
assume the peak height is the same as the area under the curve if the peak is
very narrow.

The spectra drawn should match the shift values included in the above
exercise. Heights should be appropriate for the proton environment.

1. Propan-1-ol

2. Propan-2-ol

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3. Butane

4. But-2-ene

5. Methyl benzene

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Analysing spectra

For each of the following examples analyse the high resolution proton NMR
spectrum and suggest a structural formula for each compound.

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Example 1

CH3CH2OH

OH
CH3
The OH proton and the
protons on the next door Triplet due to neighbouring
CH3 group.
carbon do not interact with
each other (under normal
circumstances) and so no
CH2
splitting is seen for the OH
Quartet due to proton.
neighbouring CH3
group. The OH proton
does not interact with
the CH2 protons and
so does not affect the
splitting.

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Example 2

CH3CH2CHO

The integral ratios on this spectrum do not

quite work out as 1:2:3 but this is a real
spectrum. The CHO peak is not appearing
as a full proton. Expanded
peak cluster
at 1.11 ppm
CH3
Triplet due to
Expanded peak neighbouring
CH2
Expanded peak cluster at 2.48 ppm
cluster at 9.79
ppm
CH2
CHO Quartet of doublets
Triplet due to arises due to splitting
splitting from
CH2
from CH3 and CHO
protons

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Example 3

CH3COOCH2CH3

CH3
Triplet due to
CH2
CH3
Singlet as there are no
protons on the adjacent
carbon atom.

Expanded peak
cluster at 4.12 ppm

CH2
Quartet due to Expanded
CH3 peak cluster
at 1.26 ppm

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Example 4

CH3CH2COOCH2CH3

Expanded
peak clusters
at 1.26 and
1.14 ppm

Expanded peak
CH3
Triplet due to
cluster at 2.32 ppm
CH3 next door
Expanded peak Triplet due to CH2.
cluster at 4.13 ppm next door
CH2
CH2.
Quartet due to next
door CH3.
CH2
Quartet due to next door CH3. This is
shifted down field due to the proximity
to the C-O.

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Example 5

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CH3COCH2CH2CH3

CH3

CH2 CH3
This is appearing as a Triplet due to next
complicated quartet due to door CH2.
CH3 group however the CH2
has an effect as well and so the
pattern is more complicated
and should be regarded as a
multiplet.

CH2
Triplet due to
next door CH2.

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Example 6

C6H5CH3

CH3

C6H5
The chemical shift tells us these protons are the
aromatic protons and this is confirmed by the ratio
of the integral curves. The pattern for phenyl
protons is complex. In this spectrum it seems there
are two proton environments for the phenyl groups.
The two protons either side of the methyl branch
and the rest of the phenyl protons.

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Example 7

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C6H5COOCH2CH3

O
CH3
C O CH2 CH3
Triplet due to
H C H CH2 next door CH2
C C
Quartet due to
C C next door CH3
H C H
H

3 phenyl H
2 phenyl H

Expanded peak
Expanded peak
cluster at 1.37 ppm
cluster at 4.36 ppm

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