Silverstein - Spectrometric Identification of Organic Compounds 7th Ed (358-550)

Chapter 8 Additional Problems 1 1
MASS
45
CI Reagent gas methane
100
169
63
100
171
50
195
75 107 139
197
89
137 50
50 m/z 100 170 180 190 200

IR
100
%Transmittance
50
3440
2877
1458
1304
1126
663
4000 3000 2000 1000
1 Wavenumber (cm-1)
1
HHNMR
NMR 300 MHz
4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 ppm
1313
C/DEPT C/DEPT NMR 75.5 MHz
75 70 65 60 55 50 45 ppm
Chapter 8 Additional Problems 2 2
MASS
% of Base Peak
97 113
100 41 100 CI Reagent gas methane
81
55 70
50 83 50 141
51 98 111 153
65
0
50 m/z 100 110 120 130 m/z
140 150
IR 100
1103
1149
90
%Transmittance
1458
2870
80
1712
2954
2931
4000 3000 2000 1000

Wavenumber (cm-1)
11
H HNMR
NMR600
300MHz
MHz
1880 1870 Hz 1800 1790 Hz 680 670 Hz 440 430 420 410 400 390 Hz
9 8 7 6 5 4 3 2 ppm
13
13C/DEPT
C/DEPT NMR
NMR150.9 MHz
75.5 MHz
180 160 140 120 100 80 60 40 20 ppm

Chapter 8 Additional Problems 3A 3
MASS
92
120
% of Base Peak
100
152
65
50 53
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
%Transmittance
50
3190
2954
1678
1616
1442
1304
1215
1092
760
702
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
4700 4680 Hz 4460 Hz 4200 4180 Hz 4120 Hz
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 ppm
13
C/DEPT NMR 600 MHz
170 160 150 140 130 120 110 100 90 80 70 60 50 ppm

Chapter 8 Additional Problems 3B 4
ppm 11 10 9 8 7 6 5 4 ppm COSY 600 MHz

4 4
5 5
6 6
7 7
F1
8 8
9 9
10 10
F2 HMQC 600 MHz

ppm
60 60
80 80
100 100
F1
120 120
140 140
160 160
11 10 9 8 7 6 5 4 ppm
F2
MASS 164
% of Base Peak
100
149
50 77 91 103 131
55 121
65
50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR
100
%Transmittance
50
3514
3016
2935
2850
1597
1512
1427
1265
1153
1034
856
791
4000 3000 2000 1000
Wavenumber (cm-1)
1
H NMR 600 MHz
1140 1120 Hz
4140 4120 Hz 3820 3800 Hz 3660 Hz
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm
13
C/DEPT NMR 150.9 MHz
140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm COSY 600 MHz
2 2
3 3
4 4
F1
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 ppm
F2
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
20
30
40
50
ppm
105
110
F1
115
120
125
130
135
140
145
150
7.0 6.5 6.0 ppm 4.0 3.9 ppm 1.9 1.8 ppm
F2
MASS 41 55 70
83
% of Base Peak
100 97
111
50 168
125 140
50 100 150
m/z
IR 100
%Transmittance
50
3078
2924
2854
1643
1466
910
4000 3000 2000 1000
Wavenumber (cm-1)
1
H NMR 300 MHz
1760 1740 Hz 1500 Hz 620 600 Hz 280 260 Hz
6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
13 C/DEPT
C NMR
NMR 75.5 75.5 MHz
MHz
29.8 29.6 29.4 29.2 29.0 ppm
140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

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 COSY 300 MHz
1 1
2 2
3 3
F1
4 4
5 5
6 6
F2
HETCO 300 MHz
ppm
1 1
2 2
3 3
F1
4 4
5 5
6 6
140 120 100 80 60 40 20 ppm

F2
MASS 93
68
% of Base Peak
100
136
79
107 121
50 53 77
40 50 60 70 80 90 100 110 120 130 140

m/z
IR
100
3078
1373
795
%Transmittance
1643
1442
887
2924
4000 3000 2000 1000

Wavenumber (cm-1)
1
H NMR 600 MHz
1050 1000 950 900 850 Hz
1300 1250 1200 1150 1100 Hz
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm

13
31.0 30.5 ppm
150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
COSY 600 MHz
ppm
1.5 1.5
2.0 2.0
ppm
2.5 2.5
1.6
3.0 3.0
F1 3.5 1.8
3.5
2.0
4.0 4.0
2.2
4.5 4.5
2.2 2.0 1.8 1.6 ppm
5.0 5.0
5.5 5.5
F2 HMQC 600 MHz

ppm
20 20
40 ppm 40
20
60 60
25
F1 80 80
30
100 100
35
120 120
40
140 140
45
2.2 2.0 1.8 1.6 ppm
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
F2
HMBC 600 MHz
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
ppm
20
25
30
35
40
F1
ppm
110
115
120
125
130
135
140
145
150
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
F2
MASS
81
67
% of Base Peak
100 152
41 109
50 53 137
123
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
50
2924
2870
1682
1612
1450
1373
1288
1211
1134
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
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
C/DEPT NMR
NMR 150.9 MHz
600 MHz
200 180 160 140 120 100 80 60 40 ppm

COSY 600 MHz

ppm 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm
1.0 1.0
1.2 1.2
1.4 1.4
1.6 1.6
1.8 1.8
F1
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 2.0 1.8 1.6 1.4 1.2 1.0 ppm
F2
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
21
22
23
24
25
26
F1
27
28
29
30
31
32
33
ppm
50
52
ppm
150
200
2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
F2
MASS
109
% of Base Peak
100
124
50 53
43
81
40 50 60 70 80 90 100 110 120

m/z
IR
100
%Transmittance
50
3124
2924
1674
1520
1296
1026
802
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
4230 4220 Hz 3670 3660 Hz 1420 1410 Hz
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
1313
C/DEPTNMR
C/DEPT NMR 150.9
600 MHzMHz
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm
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 ppm COSY 600 MHz
2 2
3 3
4 4
F1
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
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm
F2
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
F1
90 90
100 100
110 110
120 120
130 130
140 140
150 150
160 160
170 170
180 180
7.2 7.0 6.8 6.6 6.4 6.2 ppm 2.4 2.3 ppm
F2
MASS
121
% of Base Peak
100
198
50 77 105
65 93
50 100 150 200

m/z
IR
100
90
%Transmittance
80
70
3286
1635
1597
1442
1281
1149
702
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
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 ppm
13
13 C/DEPT
C/DEPTNMR
NMR600 MHz
150.9 MHz
130 129 ppm
195 190 185 180 175 170 165 160 155 150 145 140 135 130 125 120 ppm
ppm 8.0 7.8 7.6 7.4 7.2 7.0 6.8 6.6 ppm COSY 600 MHz
6.6 6.6
6.8 6.8
7.0 7.0
F1
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
8.0 7.8 7.6 7.4 7.2 7.0 6.8 6.6 ppm
F2
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 ppm
F2
MASS
43
% of Base Peak 97
100
50 55 69
140
79
40 50 60 70 80 90 100 110 120 130 140

m/z
IR
100
%Transmittance
50
2924
2854
1720
1682
1358
1072
764
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
2700 2680 Hz 2540 2520 Hz
4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 ppm
1313
C/DEPTNMR
C/DEPT NMR 150.9
600 MHzMHz
200 180 160 140 120 100 80 60 40 ppm

ppm 4.5 4.0 3.5 3.0 2.5 2.0 ppm COSY 600 MHz
2.0 2.0
ppm 2.1 2.0 1.9 1.8 1.7 ppm
2.5 2.5
1.7
1.8
F1 3.0 3.0
1.9
3.5 2.0 3.5
4.0 4.0
4.5 4.5
F2 HMQC 600 MHz
ppm
20 ppm 20
18
30 30
20
40 40
22
50 24 50
F1
60 26 60
28
70 70
2.2 2.0 1.8 ppm
80 80
90 90
4.5 4.0 3.5 3.0 2.5 2.0 ppm

F2
HMBC 600 MHz
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
4.5 4.0 3.5 3.0 2.5 2.0 ppm
F2
MASS
% of Base Peak
83
43
x 20
69
71
100
184
125
98
114
166
169
50
50 100 150
m/z
IR
100
90
%Transmittance
80
3178
2962
1728
1705
1404
1188
949
4000 3000 2000 1000
Wavenumber (cm-1)
1
H NMR 600 MHz
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 ppm
13
30.2 30.1 ppm

30.2 30.1 ppm
200 180 160 140 120 100 80 60 40 20 ppm

COSY 600 MHz

ppm 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm
1.0 1.0
1.2 1.2
1.4 1.4
1.6 1.6
1.8 1.8
F1
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 50
55 30.5 55
2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm
F2
HMBC 600 MHz
ppm 3.2 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
20
25
30
35
F1
40
45
50
55
ppm
180
190
200
210
3.2 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
F2
MASS 121
% of Base Peak 93
100 136
79
77
50 105
53 65
50 60 70 80 90 100 110 120 130 140

m/z
IR
100
1134
980
1373
825
%Transmittance
1450
2993
2870
2924
4000 3000 2000 1000

1 Wavenumber (cm-1)
H NMR 600 MHz
1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 ppm
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
130 120 110 100 90 80 70 60 50 40 30 20 ppm

ppm 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
1 1
2 2
ppm 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
1.0
F1 3 3
1.5
4 4
5 5
F2 HMQC 600 MHz

ppm
20 20
ppm
15
40 40
20
60 60
25
F1 80 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 ppm
F2
HMBC 600 MHz
5.7 5.6 ppm 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
ppm
16
18
20
22
24
F1
26
28
30
ppm
120
130
140
7 6 ppm 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
F2

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Chapter 8 Additional Problems 1 1

50 m/z 100 170 180 190 200

4000 3000 2000 1000

180 160 140 120 100 80 60 40 20 ppm

50 60 70 80 90 100 110 120 130 140 150

4700 4680 Hz 4460 Hz 4200 4180 Hz 4120 Hz

170 160 150 140 130 120 110 100 90 80 70 60 50 ppm

ppm 11 10 9 8 7 6 5 4 ppm COSY 600 MHz

F2 HMQC 600 MHz

50 60 70 80 90 100 110 120 130 140 150 160

140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

HMQC 600 MHz

1760 1740 Hz 1500 Hz 620 600 Hz 280 260 Hz

29.8 29.6 29.4 29.2 29.0 ppm

140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

140 120 100 80 60 40 20 ppm

40 50 60 70 80 90 100 110 120 130 140

4000 3000 2000 1000

1050 1000 950 900 850 Hz

1300 1250 1200 1150 1100 Hz

5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm

31.0 30.5 ppm

150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

F2 HMQC 600 MHz

HMBC 600 MHz

50 60 70 80 90 100 110 120 130 140 150

200 180 160 140 120 100 80 60 40 ppm

COSY 600 MHz

F2 HMQC 600 MHz

HMBC 600 MHz

40 50 60 70 80 90 100 110 120

4230 4220 Hz 3670 3660 Hz 1420 1410 Hz

F2 HMQC 600 MHz

HMBC 600 MHz

50 100 150 200

130 129 ppm

F2 HMQC 600 MHz

HMBC 600 MHz

40 50 60 70 80 90 100 110 120 130 140

2700 2680 Hz 2540 2520 Hz

200 180 160 140 120 100 80 60 40 ppm

3.5 2.0 3.5

4.5 4.0 3.5 3.0 2.5 2.0 ppm

HMBC 600 MHz

ppm 4.5 4.0 3.5 3.0 2.5 2.0 ppm

30.2 30.1 ppm

200 180 160 140 120 100 80 60 40 20 ppm

COSY 600 MHz

F2 HMQC 600 MHz

HMBC 600 MHz

50 60 70 80 90 100 110 120 130 140

4000 3000 2000 1000

130 120 110 100 90 80 70 60 50 40 30 20 ppm

F2 HMQC 600 MHz

HMBC 600 MHz

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