Study guide and students solutions manual for organic chemistry
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P E A R S O N
C U S T O M
L I B R A R Y
Table of Contents
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Spectroscopy Problems
1.
Determine the structure of the straight-chain pentanol that produces the mass spectrum shown here.
45
100
Relative Intensity
80
60
40
55
20
73
0
10
2.
20
30
40
50
m/z
60
70
80
The mass spectrum of an ether is shown here. Determine the molecular formula of the ether that would
produce this spectrum and then draw possible structures for it.
31
100
Relative Intensity
80
59
60
45
74
40
20
0
10
15
20
25
30
35
40
45
m/z
50
55
60
65
70
75
From Spectroscopy Problems of Study Guide and Solutions Manual for Organic Chemistry, Seventh Edition. Paula Yurkanis Bruice.
Copyright © 2014 by Pearson Education, Inc. All rights reserved.
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Spectroscopy Problems
3.
The mass spectra of pentane and isopentane are shown here. Determine which spectrum belongs to which
compound.
43
100
Relative Intensity
80
60
40
57
29
20
72
0
10
15
20
25
30
35
40
45
m/z
50
55
60
65
70
75
43
100
57
Relative Intensity
80
29
60
40
20
72
0
10
20
30
40
50
60
70
m/z
80
90
100
110
120
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Spectroscopy Problems
4.
Which of the following compounds gives the mass spectrum shown here?
O
N
O
H2N
58
100
Relative Intensity
80
60
40
73
44
20
0
10
20
25
30
35
40
45
m/z
50
55
60
65
70
75
An unknown acid underwent a reaction with 1-butanol. The product of the reaction gave the mass spectrum
shown here. What is the product of the reaction, and what acid was used?
57
100
80
Relative Intensity
5.
15
41
60
40
20
136 138
0
25
50
75
m/z
100
125
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Spectroscopy Problems
6.
Identify the compound with molecular formula C9H10O3 that gives the following IR and 1H NMR spectra.
1
3
10
9
2
2
2
8
7
6
5
4
3
2
1
0
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
A
B
S
O
R
B
A
N
C
E
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2000
1800
1600
1400
1200
1000
800
2.0
450
600
WAVENUMBERS
7.
Identify the compound with molecular formula C5H11Br that gives the following 1H NMR spectrum.
3
6
2
1
2
8
7
6
5
4
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C6H12O that gives the following IR and 1H NMR spectra.
8.
9
3
9
8
7
6
5
4
3
2
1
0
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
A
B
S
O
R
B
A
N
C
E
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
9.
A methyl-substituted benzene is treated with Cl2 in the presence of AlCl3, and a 1H NMR spectrum is taken
of one of the monochlorinated products that is isolated from the reaction mixture. Identify this compound.
3
2
8
2
7
6
5
4
3
2
1
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Spectroscopy Problems
Identify the compound with molecular formula C6H14O that gives the following IR and 1H NMR spectra.
10.
~0.9
~1.5
7
6
41 3 6
5
4
3
2
1
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
A
B
S
O
R
B
A
N
C
E
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
11.
Identify the compound with molecular formula C4H9Br that gives the following 1H NMR spectrum.
7
6
5
4
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C6H12 that gives the following IR and 1H NMR spectra.
12.
6
~4.7
~2.2
3
1
2
8
7
6
5
4
3
2
1
0
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
A
B
S
O
R
B
A
N
C
E
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
13.
Identify the compound with molecular formula C8H10O that gives the following 1H NMR spectrum.
7
6
1
2 1
7
6
5
4
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C4H7ClO that gives the following IR and 1H NMR spectra.
14.
3
3
1
8
7
6
5
4
3
2
1
0
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
A
B
S
O
R
B
A
N
C
E
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
2.0
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
15.
Identify the compound with molecular formula C8H8Br2 that gives the following 1H NMR spectrum.
4
4
8
7
6
5
4
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C4H6O that gives the following IR and 1H NMR spectra.
16.
2
8
7
6
5
3
4
1
3
2
1
0
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
A
B
S
O
R
B
A
N
C
E
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
17.
Identify the compound with molecular formula C7H8BrN that gives the following 1H NMR spectrum.
7
3
2
1
2
8
7
6
5
4
3
2
1
0
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Spectroscopy Problems
18.
The 1H NMR spectra of 1-chloro-3-iodopropane and 1-bromo-3-chloropropane are shown here. Which
compound gives which compound spectrum?
a.
7
6
5
4
3
2
1
0
1
0
b.
7
19.
6
5
4
2
Identify the compound with molecular formula C4H8O that gives the following 1H NMR spectrum.
6.4
4.0
3.8
1
8
3
7
1 1 2
6
5
4
3
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C5H10O2 that gives the following 1H NMR spectrum.
20.
5
1
8
7
6
3
5
4
3
6
2
1
0
Identify the compound with molecular formula C8H7O2Br that gives the following IR and 1H NMR spectra.
21.
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
A
B
S
O
R
B
A
N
C
E
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
1
Offset: 0.4 ppm.
8
12
11
10
2
9
2
8
2
7
6
5
4
3
2
1
0
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Spectroscopy Problems
22.
Identify the compound with molecular formula C7H6O that gives the following 1H NMR spectrum.
2
1
2
1
10
23.
9
8
7
6
5
4
3
2
1
0
The two 1H NMR spectra shown here are given by constitutional isomers with molecular formula C3H7Br.
Identify each isomer.
a.
~ 4.3
6
1
8
7
6
5
4
3
2
1
0
1
0
b.
2
2
8
7
6
5
4
2
3
3
2
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Spectroscopy Problems
24.
An unknown alkene with molecular formula C8H16 undergoes ozonolysis. Only one product is formed. The
IR and 1H NMR spectra of the product are shown here. What is the product? What alkene produced this
product?
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
A
B
S
O
R
B
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2.0
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
1
offset 2.5
~2.4
6
1
7
6
5
4
3
2
1
0
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Spectroscopy Problems
Identify the compound with molecular formula C4H7BrO2 that gives the following IR and 1H NMR spectra.
25.
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
%
T
R
A
N
S
M
I
T
T
A
N
C
E
A
B
S
O
R
B
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
2.0
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
1
offset: 0.2ppm.
6
12
26.
11
10
9
8
7
6
5
4
3
2
1
0
Identify the compound with molecular formula C3H6Cl2 that gives the following 1H NMR spectrum.
~2.2
4
2
7
6
5
4
3
2
1
0
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Spectroscopy Problems
27.
A compound with the following IR spectrum was formed by a reaction with 1-propyne. If the number of
carbons in the reactant and product is the same, what compound is formed and what reaction conditions
produced this compound?
100
0.0
90
0.05
80
0.1
70
60
50
40
30
20
A
B
S
O
R
B
A
N
C
E
%
T
R
A
N
S
M
I
T
T
A
N
C
E
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
10
2.0
0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200
2000
1800
1600
1400
1200
1000
800
600
450
WAVENUMBERS
28.
Identify the compound with molecular formula C4H8O2 that gives the following 1H and 13C NMR spectra.
CDCl3
240
220
200
QE-300
180
160
140
120
100
80
60
40
20
0
1
0
1
∼2.6 ppm.
Offset: 0.4 ppm.
1
12
11
10
9
8
7
6
5
4
3
6
2
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Spectroscopy Problems
29.
Identify the compound with molecular formula C4H8O2 that gives the following 1H NMR spectrum.
1
~11.8
2
6
30.
5
3
3
2
1
0
Identify the compound with molecular formula C9H11NO that gives the following 1H NMR spectrum.
2
1
10
31.
4
2
9
2
8
6
7
6
5
4
3
2
1
0
Identify the compound with molecular formula C9H10O2 that gives the following 1H NMR spectrum.
2
1
2
2
8
7
6
5
3
4
3
2
1
0
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Spectroscopy Problems
32.
The 13C NMR and 1H NMR spectra of1, 2-, 1, 3-, and 1, 4-ethylmethylbenzene are shown here. Determine
which spectrum belongs to which compound.
a.
160
140
120
100
80
60
40
20
0
Solvent
7
3
3
2
1
b.
3
8
7
6
5
4
3
2
1
0
160
140
120
100
80
60
40
20
0
1
0
Solvent
2
4
8
7
6
5
4
3
3
3
2
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Spectroscopy Problems
c.
160
140
120
100
80
60
40
20
0
1
0
Solvent
7
3
2
4
7
8
33.
6
5
4
3
3
2
Identify the compound with molecular formula C7H14O that gives the following 1H NMR spectrum.
~2.8 ppm
2
7
6
5
4
3
12
2
1
0
