112
CHAPTER 2
INFRARED SPECTROMETRY
Problem 2.3 Spectrum A
Problem 2.3 Spectrum B
Problem 2.3 Spectrum C
Problem 2.3
Problems 2.3 and 2.4
Problem 2.3 Spectrum D
Problem 2.4 Spectrum E
Problem 2.4 Spectrum F
PROBLEMS
113
114
CHAPTER 2
INFRARED SPECTROMETRY
Problem 2.4 Spectrum G
Problem 2.4 Spectrum H
Problem 2.4 Spectrum I
Problem 2.4
Problem 2.5
Problem 2.5 Spectrum J
Problem 2.5 Spectrum K
Problem 2.5 Spectrum L
PROBLEMS
115
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
Problem 2.6
Problem 2.6 Spectrum P
Problem 2.6 Spectrum Q
Problem 2.6 Spectrum R
PROBLEMS
117
118
CHAPTER 2
INFRARED SPECTROMETRY
Problem 2.7 Spectrum S
Problem 2.8 Spectrum T
Problems 2.7 and 2.8
Chapter 8 Additional Problems 1
MASS
1
45
CI Reagent gas methane
169
100
50
IR
89
107
m/z
100
139
137
100
195
197
75
171
63
50
50
170
180
190
200
50
4.6
4.4
4.0
3.8
3.6
663
4.2
H NMR
1126
2000
Wavenumber (cm-1)
1304
3000
1
1 H NMR 300 MHz
4.8
1458
4000
2877
3440
%Transmittance
100
1000
3.4
3.2
3.0
2.8
ppm
45
ppm
1313
C/DEPT
C/DEPT NMR 75.5 MHz
75
70
65
60
55
50
Chapter 8 Additional Problems 2
% of Base Peak
MASS
2
97
100 41
50
81
70
55
113
83
51
0
98 111
65
50
100
CI Reagent gas methane
50
141
110
100
m/z
120
153
130 m/z
140
150
1712
2870
80
4000
3000
2000
Wavenumber (cm-1)
11
H NMR 600 MHz
H NMR 300 MHz
1880
1103
1149
1458
90
2931
2954
%Transmittance
IR 100
1870
Hz 1800
9
8
1790
7
13
13C/DEPT NMR 150.9 MHz
Hz 680
Hz
670
440
6
5
4
120
100
80
1000
430
420
410
400
3
2
390
Hz
ppm
C/DEPT NMR 75.5 MHz
180
160
140
60
40
20 ppm
Chapter 8 Additional Problems 3A
3
MASS
% of Base Peak
92
120
100
50
152
65
53
50
60
70
80
90
IR
m/z
100
110
120
130
140
150
50
13
10.0
9.5
9.0
702
760
10.5
2000
Wavenumber (cm-1)
1000
4460
Hz 4200
4180 Hz
4120
8.5
8.0
7.5
7.0
6.5
6.0
5.5
130
120
110
100
90
80
4680 Hz
4700
1092
1215
1304
H NMR 600 MHz
1442
1
3000
1616
1678
4000
2954
3190
%Transmittance
100
Hz
5.0
4.5
ppm
C/DEPT NMR 600 MHz
170
160
150
140
70
60
50 ppm
Chapter 8 Additional Problems 3B
ppm 11
F1
10
9
8
7
6
5
4
4 ppm
4
4
5
5
6
6
7
7
8
8
9
9
10
10
F2
HMQC 600 MHz
ppm
F1
60
60
80
80
100
100
120
120
140
140
160
160
11
10
9
8
7
F2
COSY 600 MHz
6
5
4 ppm
Chapter 8 Additional Problems 4A
% of Base Peak
MASS
5
100
50
55
IR
149
77
65
50
60
70
80
91
103
90
100
m/z
121
110
120
131
130
140
150
160
50
2000
Wavenumber (cm-1)
791
856
1034
1153
1265
3000
1427
1512
1597
2850
2935
3016
3514
%Transmittance
100
4000
1
164
1000
H NMR 600 MHz
4140
4120
7.0
6.5
13
Hz
3820
6.0
3800 Hz
5.5
3660
5.0
1140
1120
2.5
2.0
Hz
4.5
4.0
3.5
3.0
60
50
Hz
ppm
C/DEPT NMR 150.9 MHz
140
130
120
110
100
90
80
70
40
30
20 ppm
Chapter 8 Additional Problems 4B
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
F1
6
ppm
2
2
3
3
4
4
5
5
6
6
7
7
F2
HMQC 600 MHz
ppm
20
20
40
40
60
60
F1 80
80
100
100
120
120
140
140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
F2
COSY 600 MHz
ppm
Chapter 8 Additional Problems 4C
7
HMQC 600 MHz
ppm
7.0
6.5
6.0
ppm 4.0 3.9
ppm
1.9 1.8
ppm
7.0
6.5
6.0
ppm 4.0 3.9
ppm
1.9 1.8
ppm
20
30
40
50
ppm
105
110
F1
115
120
125
130
135
140
145
150
F2
Chapter 8 Additional Problems 5A
% of Base Peak
MASS
41
55
70
83
100
97
111
50
125
50
IR
168
140
100
m/z
150
50
2000
Wavenumber (cm-1)
Hz
620
910
3000
1466
1643
2854
2924
3078
%Transmittance
100
4000
1
8
1000
H NMR 300 MHz
1760
6.0
1740
5.5
Hz
1500
5.0
4.5
4.0
600 Hz
3.5
280
3.0
260 Hz
2.5
2.0
1.5
ppm
40
30
20 ppm
13
13
C/DEPT
NMR
75.5 MHz
C
NMR 75.5
MHz
29.8
140
130
120
110
100
29.6
90
29.4
80
29.2
29.0
70
60
ppm
50
Chapter 8 Additional Problems 5B
9
ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
ppm
1
1
2
2
3
3
4
4
5
5
6
6
COSY 300 MHz
F1
F2
HETCO 300 MHz
ppm
1
1
2
2
3
3
4
4
5
5
6
6
F1
140
120
100
80
F2
60
40
20
ppm
Chapter 8 Additional Problems 6A
% of Base Peak
MASS
10
93
68
100
136
79
77
53
50
40
50
60
70
121
107
80
IR
m/z
90
100
110
120
130
140
100
887
1442
%Transmittance
795
1373
2924
1
1643
3078
4000
3000
2000
Wavenumber (cm-1)
1000
H NMR 600 MHz
1050
1300
5.5
13
5.0
4.5
1000
950
900
850
Hz
1200
1150
1100
Hz
1250
4.0
3.5
3.0
2.5
31.0
30.5 ppm
70
60
2.0
ppm
30
20 ppm
C/DEPT NMR 150.9 MHz
150
140
130
120
110
100
90
80
50
40
Chapter 8 Additional Problems 6B
ppm
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
11
1.5 ppm
COSY 600 MHz
1.5
2.0
2.0
ppm
2.5
2.5
1.6
3.0
3.0
1.8
F1 3.5
3.5
2.0
4.0
4.0
2.2
4.5
2.2
2.0
1.8
ppm
1.6
4.5
5.0
5.0
5.5
5.5
F2
HMQC 600 MHz
ppm
20
20
40
40
ppm
20
60
60
25
F1 80
80
30
100
100
35
120
120
40
140
140
45
2.2
5.5
5.0
4.5
2.0
4.0
1.8
3.5
F2
ppm
1.6
3.0
2.5
2.0
1.5 ppm
Chapter 8 Additional Problems 6C
12
HMBC 600 MHz
ppm
5.6
5.4
5.2
5.0
4.8
ppm
2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4
ppm
5.6
5.4
5.2
5.0
4.8
ppm
2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4
ppm
20
25
30
35
40
F1
ppm
110
115
120
125
130
135
140
145
150
F2
Chapter 8 Additional Problems 7A
MASS
13
% of Base Peak
81
67
100
152
109
41
53
50
50
IR
137
123
60
70
80
90
m/z
100
110
120
130
140
150
100
50
H NMR 600 MHz
1134
1211
1288
1373
1450
1
3000
1612
1682
2870
2924
4000
2000
Wavenumber (cm-1)
1000
2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0
ppm
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
200
180
160
140
120
100
80
60
40
ppm
Chapter 8 Additional Problems 7B
ppm 3.0
F1
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
14
ppm
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
1.8
1.8
2.0
2.0
2.2
2.2
2.4
2.4
2.6
2.6
2.8
2.8
F2
HMQC 600 MHz
ppm
20
20
25
25
30
30
F1 35
35
40
40
45
45
50
50
3.0
2.8
2.6
2.4
2.2
COSY 600 MHz
2.0
F2
1.8
1.6
1.4
1.2
1.0
ppm
Chapter 8 Additional Problems 7C
15
HMBC 600 MHz
ppm 2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
21
22
23
24
25
26
F1
27
28
29
30
31
32
33
ppm
50
52
ppm
150
200
2.8
F2
Chapter 8 Additional Problems 8A
16
MASS
% of Base Peak
109
100
124
50
43
40
53
81
50
60
70
80
m/z
IR
90
100
110
120
50
6.5
6.0
Hz
3670
5.5
2000
Wavenumber (cm-1)
3660
5.0
Hz
1420
4.5
802
7.0
4220
1026
4230
1296
H NMR 600 MHz
1520
1
3000
1674
4000
2924
3124
%Transmittance
100
1000
1410
4.0
Hz
3.5
3.0
2.5
ppm
30
ppm
1313
C/DEPTNMR
NMR
150.9
C/DEPT
600
MHzMHz
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
Chapter 8 Additional Problems 8B
ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
17
ppm
2
2
3
3
4
4
5
5
6
6
7
7
COSY 600 MHz
F1
F2
HMQC 600 MHz
ppm
20
20
40
40
60
60
F1 80
80
100
100
120
120
140
140
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
F2
ppm
Chapter 8 Additional Problems 8C
18
HMBC 600 MHz
ppm
7.2 7.0 6.8 6.6 6.4 6.2
2.4
2.3
ppm
20
20
30
30
40
40
50
50
60
60
70
70
80
80
90
90
100
100
110
110
120
120
130
130
140
140
150
150
160
160
170
170
180
180
F1
7.2 7.0 6.8 6.6 6.4 6.2
ppm
F2
2.4
2.3
ppm
Chapter 8 Additional Problems 9A
% of Base Peak
MASS
19
121
100
198
50
65
77
105
93
50
100
150
m/z
IR
200
90
80
70
7.3
702
7.4
H NMR 600 MHz
1149
2000
Wavenumber (cm-1)
1281
1
3000
1442
4000
1597
1635
3286
%Transmittance
100
1000
6.6
ppm
195 190 185 180 175 170 165 160 155 150 145 140 135 130 125 120
ppm
7.9
7.8
7.7
7.6
7.5
7.2
7.1
7.0
6.9
6.8
6.7
13
13
C/DEPT
MHz
C/DEPTNMR
NMR600
150.9
MHz
130
129
ppm
Chapter 8 Additional Problems 9B
ppm 8.0
F1
7.8
7.6
7.4
7.2
7.0
6.8
6.6
20
ppm
6.6
6.6
6.8
6.8
7.0
7.0
7.2
7.2
7.4
7.4
7.6
7.6
7.8
7.8
F2
HMQC 600 MHz
ppm
115
115
120
120
F1 125
125
130
130
135
135
140
140
ppm
8.0
7.8
7.6
7.4
7.2
F2
COSY 600 MHz
7.0
6.8
6.6
Chapter 8 Additional Problems 9C
21
HMBC 600 MHz
ppm 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5
ppm
115
120
ppm
128
130
132
F1
134
136
138
ppm
180
200
8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5
F2
ppm
Chapter 8 Additional Problems 10A
% of Base Peak
MASS
22
43
97
100
50
55
70
80
IR
m/z
90
100
110
120
130
1072
60
1358
50
79
1682
1720
40
140
69
140
50
4000
1
3000
H NMR 600 MHz
4.4
4.2
4.0
3.8
2000
Wavenumber (cm-1)
2700
2680 Hz
3.6
3.4
3.2
2540
3.0
764
2854
2924
%Transmittance
100
1000
2520 Hz
2.8
2.6
100
80
2.4
2.2
2.0
1.8
ppm
1313
C/DEPTNMR
NMR
150.9
C/DEPT
600
MHzMHz
200
180
160
140
120
60
40
ppm
Chapter 8 Additional Problems 10B
ppm 4.5
4.0
3.5
3.0
2.5
1.7
ppm
2.0
2.0
23
ppm
COSY 600 MHz
2.0
ppm 2.1
2.5
2.0
1.9
1.8
2.5
1.7
1.8
F1 3.0
3.0
1.9
3.5
3.5
2.0
4.0
4.0
4.5
4.5
F2
HMQC 600 MHz
ppm
20
30
20
ppm
18
30
20
40
F1
40
22
50
24
50
60
26
60
70
28
2.2
2.0
70
ppm
1.8
80
80
90
90
4.5
4.0
3.5
3.0
F2
2.5
2.0
ppm
Chapter 8 Additional Problems 10C
24
HMBC 600 MHz
ppm
4.5
4.0
3.5
3.0
2.5
2.0
ppm
4.5
4.0
3.5
3.0
2.5
2.0
ppm
20
25
ppm
90
100
F1
110
120
130
140
150
ppm
210
215
F2
Chapter 8 Additional Problems 11A
25
83
IR
100
125
166
169
50
50
150
m/z
90
80
2000
Wavenumber (cm-1)
949
1188
H NMR 600 MHz
1404
3000
1705
1728
2962
3178
%Transmittance
100
4000
1
114
98
100
184
x 20
69
71
43
% of Base Peak
MASS
1000
x64
13 12 11 10 9 ppm
2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0
13
ppm
C/DEPT NMR 150.9 MHz
200
180
160
ppm
30.2
30.1
30.2
30.1 ppm
140
120
100
80
60
40
20
ppm
Chapter 8 Additional Problems 11B
ppm 3.0
F1
2.8
2.6
2.4
2.2
2.0
1.8
1.6 1.4
1.2
1.0
26
ppm
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
1.8
1.8
2.0
2.0
2.2
2.2
2.4
2.4
2.6
2.6
2.8
2.8
F2
HMQC 600 MHz
ppm
15
15
20
20
25
25
30
30
F1 35
35
40
40
ppm
45
45
50
30.0
55
30.5
50
55
ppm
2.4 2.2 2.0 1.8 1.6 1.4 1.2
3.0
2.8
2.6
2.4
2.2
2.0
F2
COSY 600 MHz
1.8
1.6 1.4
1.2
1.0
ppm
Chapter 8 Additional Problems 11C
27
HMBC 600 MHz
ppm 3.2
3.0
2.8
2.6
2.4
2.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
20
25
30
35
F1
40
45
50
55
ppm
180
190
200
210
3.2
F2
Chapter 8 Additional Problems 12A
% of Base Peak
MASS
28
121
93
100
136
79
77
50
105
65
53
50
60
70
80
90
m/z
IR
100
110
120
130
140
825
980
1.8
5.5
13
1134
3000
2000
Wavenumber (cm-1)
1.4
1.3
H NMR 600 MHz
1.9
1373
1450
2924
4000
1
2870
2993
%Transmittance
100
1.7
5.0
1.6
1.5
4.5
4.0
3.5
90
80
1.2
1.1
1.0
3.0
1000
0.9
2.5
ppm
2.0
1.5
ppm
40
30
20 ppm
C/DEPT NMR 150.9 MHz
130
120
110
100
70
60
50
Chapter 8 Additional Problems 12B
ppm 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
1
29
ppm
1
2
ppm 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
1.0
F1 3
2
3
1.5
4
4
5
5
F2
HMQC 600 MHz
ppm
20
20
ppm
15
40
40
20
60
F1 80
COSY 600 MHz
60
25
80
30
2.5
2.0
1.5
1.0
ppm
100
100
120
120
6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
ppm
Chapter 8 Additional Problems 12C
30
HMBC 600 MHz
ppm
5.7 5.6
ppm
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
7
ppm
2.0
1.8
1.6
1.4
1.2
1.0
0.8
ppm
16
18
20
22
24
F1
26
28
30
ppm
120
130
140
6
F2