44913_08_p381-425 11/23/04 3:29 PM Page 382
STUDENT EXERCISES
Problem 8.1
% of Base Peak
MASS
68
55
100
41
112
84
50
97
70
60
50
40
IR
m/z
90
80
110
100
50
2000
Wavenumber (cm-1)
2.3
2.2
11
856
941
3000
1161
4000
1342
1454
1701
2858
2927
%Transmittance
100
1000
NMR 300 MHz
HHNMR
2.7
2.6
2.5
2.4
2.1
2.0
1.9
1.8
1.7
1.5 ppm
1.6
1313
C/DEPT NMR 75.5 MHz
C/DEPT
200
180
160
140
120
100
80
60
40
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 383
Problem 8.2
MASS
% of Base Peak
124
100
94
50
80
70
60
50
95
81
66
53
m/z
IR
120
110
100
90
50
11
687
768
837
945
1041
1149
3000
1284
4000
1493
1601
2839
2947
3005
3398
%Transmittance
100
2000
Wavenumber (cm-1)
1000
H NMR
NMR 300 MHz
H
2150
7.5
7.0
2140
6.5
Hz
1960
6.0
1950
Hz
5.5
1930
1920 Hz
4.5
5.0
3.5
4.0
ppm
13
13
C/DEPT NMR 75.5 MHz
C/DEPT
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 384
Problem 8.3
MASS
% of Base Peak
55
M-1
83
100
39 41
M
50
53
55
50
45
40
65
IR
m/z
85
80
75
70
65
60
84
66
50
741
2000
Wavenumber (cm-1)
1014
11
1138
1227
1319
3000
1454
4000
2229
2291
2877
2939
2978
3332
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
1280
1260 Hz
ppm
1.5
2.0
2.5
3.0
3.5
4.0
660 Hz
680
13
13C/DEPT
C/DEPT NMR 75.5 MHz
CDCl3
78.0 77.5 77.0 76.5
95
90
85
80
75
70
65
p pm
60
55
50
45
40
35
30
25
20
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 385
Problem 8.4
MASS
% of Base Peak
75
CI Reagent gas methane
100
49
61
50
77
99
97
50
m/z
100
112 M
114
IR
x 30
111
110
113
146
148
146
75
77
50
150
100
115
100
148
150
152
150
m/z
90
80
70
H NMR
NMR 300 MHz
4.30
4.35
4.20
4.25
4.15
4.10
4.05
4.00
3.95
663
717
11
H
2000
Wavenumber (cm-1)
910
3000
1219
1288
4000
1435
2962
3016
%Transmittance
100
1000
3.85
3.90
3.80
ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
75
70
65
60
55
50
45
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 386
Problem 8.5
% of Base Peak
MASS
m/z
126 (M)
127 (M+1)
128 (M+2)
100
50
%M
100.0
8.2
4.9
111
126
39
43
40
83
57
49
50
70
60
IR
110
100
90
80
m/z
130
120
50
590
2000
Wavenumber (cm-1)
725
856
933
1061
11
1273
3000
1415
4000
1662
3089
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
2300
7.5
7.0
6.5
6.0
5.5
2280 Hz
2140
5.0
4.5
2120 Hz
2.5
3.0
3.5
4.0
ppm
13
13 C/DEPT
C/DEPT NMR 75.5 MHz
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 387
Problem 8.6
% of Base Peak
MASS
x 10
105
100
50
186
184
77
51
100
50
IR
150
m/z
100
80
70
2260
7.5
13
2240
2250
7.0
2230
6.5
2220
6.0
2210
5.5
1000
1590
1580
1570
Hz
640
630
620
Hz
Hz
2200
5.0
594
694
764
H NMR 300 MHz
2000
Wavenumber (cm-1)
964
3000
1211
4000
1
1450
1496
2985
3032
%Transmittance
90
2.5
3.0
3.5
4.0
4.5
ppm
C/DEPT NMR 75.5 MHz
140
130
120
110
100
90
80
70
60
50
40
30 ppm
44913_08_p381-425 11/23/04 3:29 PM Page 388
Problem 8.7
MASS
% of Base Peak
109
124
100
81
53
50
63
75
80
70
60
50
IR
m/z
120
110
100
90
50
513
733
825
2000
Wavenumber (cm-1)
1034
11
1234
3000
1512
1612
1701
4000
1859
2835
2951
3348
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
6.0
6.5
7.0
ppm
3.5
4.0
4.5
5.0
5.5
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
150
140
130
120
110
100
90
80
70
60
50
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 389
Problem 8.8
MASS
% of Base Peak
128
100
64
130
50
92
73
80
70
60
50
IR
m/z
90
130
120
110
100
50
11
H
H NMR
NMR 300 MHz
7.2
6.8
7.0
2000
Wavenumber (cm-1)
6.6
6.4
6.2
679
748
3000
1030
4000
7.4
1200
1338
1454
1481
1585
3039
3074
3464
3521
%Transmittance
100
1000
6.0
5.6
5.8
5.4
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
155
150
145
140
135
130
125
120
115
ppm
44913_08_p381-425 11/23/04 3:29 PM Page 390
Problem 8.9
x 20
55
87
100
115
196
194
73
135
0
100
50
137
165
150
m/z
IR
163
1203
50
1365
1435
% of Base Peak
MASS
50
3000
2000
Wavenumber (cm-1)
1
1H
H NMR
NMR 300 MHz
3.6
3.4
3.2
3.0
2.4
2.6
2.8
748
4000
1736
2954
%Transmittance
100
1000
2.0
2.2
1.6
1.8
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
33.0
32.5
170 160 150 140 130 120 110 100
32.0
ppm
90
80
70
60
50
40
30
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 391
Problem 8.10
MASS
% of Base Peak
54
100
67
84
93
50
111
80
70
60
50
IR
m/z
120
110
100
90
126
H NMR
NMR 300 MHz
1000
1.0
1.5
2.0
2.5
3.0
3.5
2000
Wavenumber (cm-1)
849
11
H
1045
3000
1331
4000
1466
2873
2931
2958
3344
%Transmittance
100
ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
84
82
85
80
80
78
75
ppm
70
65
60
55
50
45
40
35
30
25
20
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 392
Problem 8.11
MASS
% of Base Peak
162
100
164
63
98
50
126
73
50
90
80
70
60
IR
120
100 110
m/z
128
130
160
150
140
50
3000
11
H
H NMR
NMR 300 MHz
7.4
7.2
7.0
6.8
2000
Wavenumber (cm-1)
6.6
6.2
6.4
6.0
555
4000
725
814
1188
1277
1404
1477
1585
3097
3521
%Transmittance
100
1000
5.8
5.6
5.4
5.2 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
155
150
145
140
135
130
125
120
115
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 393
Problem 8.12
% of Base Peak
MASS
123
100
95
75
50
50
63
70
60
50
IR
138
90
m/z
80
140
130
120
110
100
50
2400
2390
2380
Hz
2140
2130
1000
19
F NMR 282.4 MHz
1
H Coupled
1
H Decoupled
Hz
ppm
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
13
567
H NMR 300 MHz
841
960
2000
Wavenumber (cm-1)
1157
1265
1358
1
3000
1597
1685
4000
3005
3074
3356
%Transmittance
100
-104.5 ppm
-104.4
C/DEPT NMR 75.5 MHz
130 128 126 124 122 120 118
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
ppm
40
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 394
Problem 8.13
MASS
% of Base Peak
96
100
50
70
50
65
60
55
50
IR
70
m/z
75 77
95
90
85
80
75
95
3000
2000
Wavenumber (cm-1)
11H
1000
19
NMR 300 MHz
H NMR
F NMR 282.4 MHz
1
7.1
7.2
7.3
7.4
ppm
756
4000
1234
1504
1604
1697
3062
3749
%Transmittance
100
-80.1
H Coupled
-80.3 ppm
-80.2
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
130
165
128
160
126
124
155
122
150
120
145
118
140
116 ppm
135
130
125
120
115 ppm
44913_08_p381-425 11/23/04 3:30 PM Page 395
Problem 8.14
MASS
% of Base Peak
82
100
50
138
54
95
67
90
m/z
80
70
60
50
IR
123
100
110
120
130
140
50
6.0
1740 Hz
5.5
640
570
4.0
4.5
5.0
560 Hz
300
3.5
3.0
525
Hz
H NMR
NMR 300 MHz
903
2000
Wavenumber (cm-1)
1246
3000
11
H
1381
4000
1750
1670
2870
2958
%Transmittance
100
1000
290
2.5
Hz
2.0
1.5
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
200
180
160
140
120
100
80
60
40
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 396
Problem 8.15
MASS
% of Base Peak
54
68
50
81
79
60
50
93
90
80
70
IR
95
m/z
107
100
109
149
147
119
121
120
110
130
140
150
100
%Transmittance
90
80
11
756
3000
1250
4000
1435
2245
2970
70
2000
Wavenumber (cm-1)
1000
H
H NMR
NMR 300 MHz
3.6
3.5
3.4
3.3
3.2
3.1
3.0
2.8
2.9
2.7
2.6
2.5
2.4
2.3
ppm
2.2
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
120
110
100
90
80
70
60
50
40
30
20
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 397
Problem 8.16
MASS
% of Base Peak
106
100
137
50
77
80
70
60
50
IR
m/z
130
120
110
100
90
140
90
80
H NMR
NMR 300 MHz
7.5
7.0
5.5
6.0
6.5
2
3
4
5
2000
Wavenumber (cm-1)
5.0
825
3000
11
H
1049
4000
1442
1512
1620
2931
3194
3348
%Transmittance
100
1000
ppm
4.5
4.0
3.5
2.5
3.0
2.0
1.5 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
140
130
120
110
100
90
80
70
60
50
40
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 398
Problem 8.17
MASS
% of Base Peak
119
100
50
91
64
76
IR
110
100
90
80
m/z
70
60
50
120
90
80
70
H NMR
NMR 300 MHz
7.6
7.5
7.4
7.3
7.2
7.1
671
787
1
1H
1342
3000
1481
1589
4000
2245
3309
%Transmittance
100
2000
Wavenumber (cm-1)
7.0
6.9
6.8
6.7
6.6
1000
6.5
6.4
6.3
6.2
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
165
160
155
150
145
140
135
130
125
120
115
110
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 399
Problem 8.18
MASS
% of Base Peak
163
100
178
50
91
77
135
100
50
IR
150
m/z
50
3000
11
2000
Wavenumber (cm-1)
748
4000
1149
1203
1458
2870
2962
3572
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
2150
6.5
7.0
2100 Hz
5.5
6.0
950 Hz
1000
5.0
450
4.5
4.0
90
80
400
3.5
Hz
2.0
2.5
3.0
1.5 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
150
140
130
120
110
100
70
60
50
40
30
20 ppm
44913_08_p381-425 11/23/04 3:30 PM Page 400
Problem 8.19
MASS
% of Base Peak
106
78
100
121
51
50
80
m/z
70
60
50
IR
120
110
100
90
50
2720
9.0
2700 Hz
8.5
8.0
2600
7.5
2000
Wavenumber (cm-1)
2580 Hz
7.0
6.5
2440
6.0
2420 Hz
5.5
1000
2180 Hz
2200
5.0
702
H NMR
NMR 300 MHz
957
11
H
1273
3000
1419
1689
4000
3047
3363
%Transmittance
100
4.0
4.5
3.5
3.0
ppm
40
ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
44913_08_p381-425 11/23/04 3:30 PM Page 401
Problem 8.20
MASS
% of Base Peak
108
123
100
53
50
70
60
50
40
80
IR
80
m/z
90
120
110
100
50
2060
7.0
6.5
Hz
5.5
1000
Hz
Hz 1820
2020
6.0
2000
Wavenumber (cm-1)
633
741
H NMR
NMR 300 MHz
1095
1
1H
1404
3000
1651
4000
2947
3109
%Transmittance
100
5.0
4.5
120
100
4.0
3.5
2.5
3.0
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
180
160
140
80
60
40
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 402
Problem 8.21
% of Base Peak
MASS
100
50
103
158
50
187
150
150
100
m/z
IR
159
100
85
57
50
CI Reagent gas methane
x 20
43
m/z
50
11
2000
Wavenumber (cm-1)
1034
1149
3000
1319
4000
1651
1720
2962
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
1.0
1.5
2.0
2.5
3.0
3.5
ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
200
180
160
140
120
100
80
60
40
ppm
44913_08_p381-425 11/23/04 3:30 PM Page 403
Problem 8.22
% of Base Peak
MASS
119
100
50
91
64
76
70
60
50
90
80
m/z
IR
100
110
120
90
80
70
H NMR 300 MHz
7.4
13
7.3
7.2
7.1
7.0
6.9
2000
Wavenumber (cm-1)
6.8
6.7
6.6
671
787
1
3000
1342
4000
1481
1589
2245
3309
%Transmittance
100
1000
6.5
6.4
6.3
6.2
ppm
C/DEPT NMR 75.5 MHz
155
150
145
140
135
130
125
120
115
ppm
44913_08_p381-425 11/23/04 3:31 PM Page 404
Problem 8.23
MASS
% of Base Peak
x 20
183
100
155
75
50
185
157
226
250
200
150
m/z
100
IR
224
200
198
264
262
260
50
7.8
7.7
7.6
ppm
3.6
3.4
617
7.9
810
H NMR
NMR 300 MHz
2000
Wavenumber (cm-1)
995
1068
11
H
1223
3000
1396
1485
1585
1685
4000
2962
3059
3089
3356
%Transmittance
100
1000
3.2
3.0
90
80
2.8
2.4
2.6
ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
190 180 170 160 150 140 130 120 110 100
70
60
50
40
ppm
44913_08_p381-425 11/23/04 3:31 PM Page 405
Problem 8.24
% of Base Peak
MASS
100
100
CI Reagent gas methane
55
50
147
69
74
83
50
128
175
150
100
50
150
187
200
m/z
m/z
IR
50
H NMR
NMR 300 MHz
930
11
H
1238
1277
1419
1466
3000
1709
4000
2669
2978
3039
%Transmittance
100
2000
Wavenumber (cm-1)
1000
x64
12
11
ppm
2.6
2.4
2.0
2.2
1.8
1.6
1.2 ppm
1.4
13
13C/DEPT
C/DEPT NMR 75.5 MHz
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
44913_08_p381-425 11/23/04 3:31 PM Page 406
Problem 8.25
91
66
100
93
92
CI Reagent gas methane
50
100
51
% of Base Peak
MASS
50
60
50
IR
m/z
80
90
80
70
90
m/z
90
80
725
802
1065
3000
1342
4000
1
1720
2962
3055
%Transmittance
100
2000
Wavenumber (cm-1)
1000
H NMR 300 MHz
7.0
13
6.5
Hz
2040
2050
6.0
5.5
1080 Hz
1090
3.5
4.0
4.5
5.0
Hz
615 610 605
3.0
2.5
2.0
ppm
50
ppm
C/DEPT NMR 75.5 MHz
140
130
120
110
100
90
80
70
60
44913_08_p381-425 11/23/04 3:31 PM Page 407
Problem 8.26
% of Base Peak
MASS
M
156
100
M+2
63
158
50
98
70
60
50
90
80
IR
121
110
100
m/z
120
130
140
160
150
6.80
6.85
2000
Wavenumber (cm-1)
6.70
6.75
6.65
ppm
125
120
1041
H NMR 600 MHz
1234
1473
3000
802
933
50
4000
1
586
2900
%Transmittance
100
1000
6.00 5.95
ppm
1313
C/DEPT
MHz
C/DEPTNMR
NMR600
150.9
MHz
155
150
145
140
135
130
115
110
105 ppm