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112 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.3 Spectrum A
Problem 2.3 Spectrum B
Problem 2.3 Spectrum C
Problem 2.3 
PROBLEMS 113
Problem 2.3 Spectrum D
Problem 2.4 Spectrum E
Problem 2.4 Spectrum F
Problems 2.3 and 2.4 
114 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.4 Spectrum G
Problem 2.4 Spectrum H
Problem 2.4 Spectrum I
Problem 2.4 
PROBLEMS 115
Problem 2.5 Spectrum J
Problem 2.5 Spectrum K
Problem 2.5 Spectrum L
Problem 2.5 
116 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.5 Spectrum M
Problem 2.6 Spectrum N
Problem 2.6 Spectrum O
Problems 2.5 and 2.6 
PROBLEMS 117
Problem 2.6 Spectrum P
Problem 2.6 Spectrum Q
Problem 2.6 
Problem 2.6 Spectrum R
118 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.7 Spectrum S
Problem 2.8 Spectrum T
Problems 2.7 and 2.8 
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 Chapter 8 Additional Problems
1
2.83.03.23.43.63.84.04.24.44.64.8 ppm
45505560657075 ppm
13C/DEPT 
1H NMR 
MASS 
IR 
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
itt
an
ce
663
1126
1304
1458
2877
3440
10050
50
100
45
63
75 89 107
137
139
200190180170
50
100
16
9
17
1
19
5
19
7
CI Reagent gas methane
13C/DEPT NMR 75.5 MHz 
1H NMR 300 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
1 
 Chapter 8 Additional Problems 2
23456789 ppm
20406080100120140160180 ppm
MASS 
IR 
1H NMR 600 MHz 
13C/DEPT NMR 150.9 MHz 
%
 o
f 
B
as
e 
Pe
ak
m/z 10050
0
50
100 41
51
55
65
70 81
83
97
98 111
150140130120110
50
100
113
141 153
m/z
CI Reagent gas methane
4000 3000 2000 1000
Wavenumber (cm-1)
80
90
100
%
T
ra
ns
m
it
ta
nc
e
2954
2931
2870 1712
1458
1149
1103
670680 Hz18701880 Hz 17901800 Hz 390400410420430440 Hz
13C/DEPT NMR 75.5 MHz 
1H NMR 300 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
2 
 Chapter 8 Additional Problems 3
 
4.55.05.56.06.57.07.58.08.59.09.510.010.5 ppm
5060708090100110120130140150160170 ppm
MASS 
46804700 Hz
IR 
1H NMR 600 MHz 
13C/DEPT NMR 600 MHz 
4120 Hz41804200 Hz4460 Hz
%
 o
f 
B
as
e 
Pe
ak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
it
ta
nc
e
702
760
1092
1215
1304
1442
1616
1678
2954
3190
1501401301201101009080706050
50
100
53
65
92
120
152
 
3A 
 Chapter 8 Additional Problems 4
4567891011ppm ppm
4
5
6
7
8
9
10
4
5
6
7
8
9
10
ppm
4567891011 ppm
60
80
100
120
140
160
60
80
100
120
140
160
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
 
3B 
 Chapter 8 Additional Problems 5
2.02.53.03.54.04.55.05.56.06.57.0 ppm
2030405060708090100110120130140 ppm
MASS 
IR 
1H NMR 600 MHz 
3660 Hz41204140 Hz
11201140 Hz
38003820 Hz
13C/DEPT NMR 150.9 MHz 
%
 o
f 
B
as
e 
Pe
ak
m/z
1601501401301201101009080706050
50
100
164
149
13112110391
77
65
55
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
itt
an
ce
3514
3016
2935
2850
1597
1512
1427
1265
1153
1034
856
791
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
4A 
 Chapter 8 Additional Problems 6
2.02.53.03.54.04.55.05.56.06.57.0ppm ppm
2
3
4
5
6
7
2
3
4
5
6
7
ppm
2.02.53.03.54.04.55.05.56.06.57.0 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
4B 
 Chapter 8 Additional Problems 7
ppm
6.06.57.0 ppm
105
110
115
120
125
130
135
140
145
150
3.94.0 ppm 1.81.9 ppm
6.06.57.0ppm ppm
20
30
40
50
3.94.0 ppm 1.81.9 ppm
HMQC 600 MHz 
 
F1 
F2 
4C 
 Chapter 8 Additional Problems 8
1.52.02.53.03.54.04.55.05.56.0 ppm
2030405060708090100110120130140 ppm
MASS 
IR 
1500 Hz 600620 Hz17401760 Hz
%
 o
f 
B
as
e 
Pe
ak
m/z
15010050
50
100
168
140125
111
97
83
705541
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
itt
an
ce
3078
2924
2854
1643
1466
910
260280 Hz
13C NMR 75.5 MHz 
1H NMR 300 MHz 
2030405060708090100110120130140 ppm
29.029.229.429.629.8 ppm
13C/DEPT NMR 75.5 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
5A 
 Chapter 8 Additional Problems 9
1.01.52.02.53.03.54.04.55.05.56.06.5ppm ppm
1
2
3
4
5
6
1
2
3
4
5
6
ppm
20406080100120140 ppm
1
2
3
4
5
6
1
2
3
4
5
6
F2 
F2 
F1 
F1 
COSY 300 MHz 
HETCO 300 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
5B 
 Chapter 8 Additional Problems 10
2.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130140150 ppm
MASS 
11001150120012501300 Hz
IR 
%
 o
f 
B
as
e 
Pe
ak
m/z
140130120110100908070605040
50
100
53
68
77
79
93
107 121
136
4000 3000 2000 1000
Wavenumber (cm-1)
100
%
T
ra
ns
m
it
ta
nc
e
795
887
1373
1442
1643
2924
3078
85090095010001050 Hz
30.531.0 ppm
1H NMR 600 MHz 
13C/DEPT NMR 150.9 MHz 
 
6A 
 Chapter 8 Additional Problems 11
1.52.02.53.03.54.04.55.05.5ppm ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
ppm
1.52.02.53.03.54.04.55.05.5 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
ppm
1.61.82.02.2 ppm
20
25
30
35
40
45
ppm
1.61.82.02.2 ppm
1.6
1.8
2.0
2.2
 
6B 
 Chapter 8 Additional Problems 12
1.41.51.61.71.81.92.02.1 ppm
F2 
F1 
HMBC 600 MHz 
4.85.05.25.45.6
ppm
ppm
20
25
30
35
40
ppm
4.85.05.25.45.6 ppm
110
115
120
125
130
135
140
145
150
1.41.51.61.71.81.92.02.1 ppm
 
6C 
 Chapter 8 Additional Problems 13
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm
406080100120140160180200 ppm
MASS 
IR 
1H NMR 600 MHz 
13C/DEPT NMR 600 MHz 
%
 o
f 
B
as
e 
Pe
ak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
1134
1211
1288
1373
1450
1612
1682
2870
2924
1501401301201101009080706050
50
100
41
53
67
81
109
123
137
152
13C/DEPT NMR 150.9 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
7A
Chapter 8 Additional Problems 14
1.01.21.41.61.82.02.22.42.62.83.0ppm ppm
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
ppm
1.01.21.41.61.82.02.22.42.62.83.0 ppm
20
25
30
35
40
45
50
20
25
30
35
40
45
50
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
 
7B 
 Chapter 8 Additional Problems 15
F2 
F1 
HMBC 600 MHz 
ppm
0.81.01.21.41.61.82.02.22.42.62.8 ppm
150
200
0.81.01.21.41.61.82.02.22.42.62.8ppm ppm
21
22
23
24
25
26
27
28
29
30
31
32
33
ppm
50
52
 
 
7C 
 Chapter 8 Additional Problems 16
2.53.03.54.04.55.05.56.06.57.0 ppm
30405060708090100110120130140150160170180 ppm
MASS 
IR 
1H NMR 600 MHz 
13C/DEPT NMR 600 MHz 
42204230 Hz 14101420 Hz36603670 Hz
%
 o
f 
B
as
e 
Pe
ak
m/z
120110100908070605040
50
100
124
109
81
5343
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
it
ta
nc
e
3124
2924
1674
1520
1296
1026
802
13C/DEPT NMR 150.9 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
8A 
 Chapter 8 Additional Problems 17
2.02.53.03.54.04.55.05.56.06.57.07.5ppm ppm
2
3
4
5
6
7
2
3
4
5
6
7
ppm
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
 
8B 
 Chapter 8 Additional Problems 18
2.32.4 ppm
2.32.4 ppm
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
F2 
F1 
HMBC 600 MHz 
6.26.46.66.87.07.2ppm
6.26.46.66.87.07.2 ppm
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
 
8C 
 Chapter 8 Additional Problems 19
6.66.76.86.97.07.17.27.37.47.57.67.77.87.9 ppm
120125130135140145150155160165170175180185190195 ppm
MASS 
IR 
1H NMR 600 MHz 
13C/DEPT NMR 600 MHz 
129130 ppm
%
 o
f 
B
as
e 
Pe
ak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
70
80
90
100
%
T
ra
ns
m
it
ta
nc
e
3286
1635
1597
1442
1281
1149
702
20015010050
50
100
198
121
105
937765
13C/DEPT NMR 150.9 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
9A 
 Chapter 8 Additional Problems 20
6.66.87.07.27.47.67.88.0ppm ppm
6.6
6.8
7.0
7.2
7.4
7.6
7.8
6.6
6.8
7.0
7.2
7.4
7.6
7.8
ppm
6.66.87.07.27.47.67.88.0 ppm
115
120
125
130
135
140
115
120
125
130
135
140
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
 
9B 
 Chapter 8 Additional Problems 21
ppm
128
130
132
134
136
138
F2 
F1 
HMBC 600 MHz 
ppm
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0 ppm
180
200
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0ppm ppm
115
120
 
9C 
 Chapter 8 Additional Problems 22
1.82.02.22.42.62.83.03.23.43.63.84.04.24.4 ppm
406080100120140160180200 ppm
MASS 
IR 
1H NMR 600 MHz 
13C/DEPT NMR 600 MHz 
26802700 Hz
%
 o
f 
B
as
e 
Pe
ak
m/z
140130120110100908070605040
50
100
43
55 69 79
97
140
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%
T
ra
ns
m
it
ta
nc
e
764
1072
1358
1682
1720
2854
2924
25202540 Hz
13C/DEPT NMR 150.9 MHz 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
10A 
 Chapter 8 Additional Problems 23
2.02.53.03.54.04.5ppm ppm
2.0
2.5
3.0
3.5
4.0
4.5
2.0
2.5
3.0
3.5
4.0
4.5
ppm
2.02.53.03.54.04.5 ppm
20
30
40
50
60
70
80
90
20
30
40
50
60
70
80
90
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
ppm
1.82.02.2 ppm
18
20
22
24
26
28
1.71.81.92.02.1ppm ppm
1.7
1.8
1.9
2.0
 
10B 
 Chapter 8 Additional Problems 24
ppm
90
100
110
120
130
140
150
F2 
F1 
HMBC 600 MHz 
ppm
2.02.53.03.54.04.5 ppm
210
215
2.02.53.03.54.04.5ppm ppm
20
25
 
10C 
 Chapter 8 Additional Problems 25
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9 ppm
200 180 160 140 120 100 80 60 40 20 ppm
MASS 
IR 
910111213 ppm
13C/DEPT NMR 150.9 MHz 
1H NMR 600 MHz 
%
 o
f 
B
as
e 
Pe
ak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
80
90
100
%
T
ra
ns
m
itt
an
ce
949
1188
1404
1705
1728
2962
3178
15010050
50
100
x 204
3
69 71
83
98
11
4 12
5
16
6
16
9 1
84
x64
30.130.2 ppm
 
30.130.2 ppm 
11A 
 Chapter 8 Additional Problems 26
1.01.21.41.61.82.02.22.42.62.83.0ppm ppm
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
ppm
1.01.21.41.61.82.02.22.42.62.83.0 ppm
15
20
25
30
35
40
45
50
55
15
20
25
30
35
40
45
50
55
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
ppm
1.21.41.61.82.02.22.4 ppm
30.0
30.5
 
11B 
 Chapter 8 Additional Problems 27
0.81.01.21.41.61.82.02.22.42.62.83.03.2ppm ppm
20
25
30
35
40
45
50
55
F2 
F1 
HMBC 600 MHz 
ppm
0.81.01.21.41.61.82.02.22.42.62.83.03.2 ppm
180
190
200
210
 
11C 
 Chapter 8 Additional Problems 28
1.52.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130 ppm
MASS 
IR 
%
 o
f 
B
as
e 
Pe
ak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
100
%
T
ra
ns
m
it
ta
nc
e
825
980
113413731450
2870
2924
2993
1401301201101009080706050
50
100
53 65
77
79
93
105
121
136
0.91.01.11.21.31.41.51.61.71.81.9 ppm
13C/DEPT NMR 150.9 MHz 
1H NMR 600 MHz 
 
12A 
 Chapter 8 Additional Problems 29
1.01.52.02.53.03.54.04.55.05.56.0ppm
ppm
1
2
3
4
5
1
2
3
4
5
ppm
1.01.52.02.53.03.54.04.55.05.56.0 ppm
20
40
60
80
100
120
20
40
60
80
100
120
F2 
F2 
F1 
F1 
HMQC 600 MHz 
COSY 600 MHz 
ppm
1.01.52.02.5 ppm
15
20
25
30
0.81.01.21.41.61.82.0ppm ppm
1.0
1.5
 
12B 
 Chapter 8 Additional Problems 30
0.81.01.21.41.61.82.0 ppm
F2 
F1 
HMBC 600 MHz 
5.65.7
ppm
ppm
16
18
20
22
24
26
28
30
ppm
67 ppm
120
130
140
0.81.01.21.41.61.82.0 ppm
 
12C 
		Preface
		Contents
		Chapter 1: Mass Spectrometry
		Chapter 2: Infrared Spectrometry
		Aditional Problems Chapter 2
		Chapter 3: Proton NMR Spectrometry
		Chapter 4: carbon-13 NMR Spectrometry
		Chapter 5: Correlation NMR Spectrometry; 2-D NMR
		Chapter 6: NMR Spectrometry of Other Important Spin 1/2 Nuclei
		Chapter 7: Solved Problems
		Aditional Problems Chapter 8
		Index

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