13.

Structure Determination:
Nuclear Magnetic Resonance
Spectroscopy
13.1 Give the chemical shift for
aromatic protons in an 1H NMR
spectrum.
a.  1.4 d.  7.2
b.  2.5 e.  10
c.  4.0
13.1 Answer
a.  1.4 d.  7.2
b.  2.5 e.  10
c.  4.0

Aromatic protons have an approximate

chemical shift of  7.2.
13.2 Identify carbon–1 in the 1H
NMR spectrum of 1-
chlorobutane.

a. 1.0 (3H)
b. 1.3 (2H)
c. 1.7 (2H)
d. 3.4 (2H)
13.2 Answer

a. 1.0 (3H)
b. 1.3 (2H)
c. 1.7 (2H)
d. 3.4 (2H)

Chlorine causes the NMR signal to shift

to a higher value.
13.3 Identify a compound that
has a formula of C5H10O and an
1
H NMR signal at 2.5.
a.A carboxylic acid b.An ester
c.A ketone d.An alcohol
13.3 Answer

a.A carboxylic acid b.An ester

c.A ketone d.An alcohol

An 1H NMR signal at  2~3 indicates

A ketone.
13.4 Interpret a quartet in an 1H
spectrum.
a.Two protons are on adjacent carbons.
b.Three protons are on adjacent carbons.
c.Four protons are on adjacent carbons.
d.Five protons are on adjacent carbons.
e.Six protons are on adjacent carbons.
13.4 Answer

a.Two protons are on adjacent carbons.

b.Three protons are on adjacent carbons.
c.Four protons are on adjacent carbons.
d.Five protons are on adjacent carbons.
e.Six protons are on adjacent carbons.

A quartet indicates that three protons are on

adjacent carbons.
13.5 Predict the number of
signals in an 1H NMR spectrum
for (CH3)2CHOCH2CH3.
a.One signal
b.Two signals
c.Three signals
d.Four signals
e.Five signals
13.5 Answer

a.One signal
b.Two signals
c.Three signals
d.Four signals
e.Five signals

The methyls are in identical environments, so

there are four signals.
13.6 Identify the compound with
a formula of C4H8O and an 1H
NMR spectrum of 1.1 (t, 3H),
2.1 (s, 3H), and 2.5 (q, 2H).
a.CH3CH2CH2OCH3
b.CH3CH2C(=O)CH3
c.CH3CH2CH2CHO
d.CH3CH2CH2CH2OH
13.6 Answer
a.CH3CH2CH2OCH3
b.CH3CH2C(=O)CH3
c.CH3CH2CH2CHO
d.CH3CH2CH2CH2OH
Ethyl group: 1.1 (t, 3H), 2.1 (s, 3H), and 2.5 (q, 2H).

The compound has an ethyl and a methyl

separated by a carbonyl group.
13.7 Identify a compound with a
formula of C9H12 and an 1H NMR
spectrum of 1.0 (t, 3H), 1.7 (sext,
2H), 2.6 (t, 2H), 7.2 (m, 5H).

a.C6H5CH2CH2CH3
b.C6H5CH(CH3)2
c.C6H5CH2CH2CH2CH3
d.C6H5CH2CH(CH3)2
13.7 Answer

a.C6H5CH2CH2CH3
b.C6H5CH(CH3)2
c.C6H5CH2CH2CH2CH3
d.C6H5CH2CH(CH3)2

From the splitting, the compound contains an

isopropyl attached to a benzene.
 Which of the following molecules best fits the
13.8 following 1H NMR spectrum?

C9H12
6
5
1

1. 2.

3.

4. 5.
13.8 Answer

3.

isopropyl group

1.3 (double, 6H), and 2.5 (septet, 1H).

 Which of the following molecules best fits the
13.9
following 1H NMR spectrum?

1. 2.
O O

OCH3
3.
O

O 5.
4. O
O
OH
OH
13.9 Answer
O
3.
O
13.10
What is the relationship between Ha and Hb
in the following compound?
OH
Hc
Ha Hb

1. chemically unrelated
2. homotopic
3. enantiotopic
4. diastereotopic
5. none of these
13.9 Answer
2. homotopic
13.10
What is the relationship between Ha and Hb
in the following compound?
Cl
Ha
Hb

1. chemically unrelated
2. homotopic
3. enantiotopic
4. diastereotopic
5. none of these
13.10 Answer
4. diastereotopic
13.11 Give the type of group
indicated by a peak at 20 in a
13
C NMR spectrum.
a.Aromatic d.Halogen
b.Ether e.Alkane
c.Alcohol
13.11 Answer
a.Aromatic d.Halogen
b.Ether e.Alkane
c.Alcohol

A peak at 20 indicates an alkane(40).

13.12 Give the type of group
indicated by a peak at 180 in a
13
C NMR spectrum.
a.Aromatic d.Halogen
b.Ether e.Carbonyl
c.Alcohol
13.12 Answer
a.Aromatic d.Halogen
b.Ether e.Carbonyl
c.Alcohol

A peak at 180 indicates a carbonyl

compound.
13.13 Where do the alkene
peaks appear in a 13C NMR
spectrum?
a.20 ppm d.130 ppm
b.50 ppm e.180 ppm
c.80 ppm
13.13 Answer
a.20 ppm d.130 ppm
b.50 ppm e.180 ppm
c.80 ppm

The alkene peaks give a 13C NMR

signal from 100 to 150 ppm.
13.14
How many signals will appear in the 13C
NMR spectrum of the following molecule?

1. 1
2. 2
3. 3
4. 4
5. 5
13.14 Answer
5. 5
13.15
How many signals will appear in the 13C
NMR spectrum of the following molecule?
OCH3

1. 3
2. 4
3. 5
4. 6
5. 7
13.15 Answer
4. 6