Problem 8.1
1.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm
406080100120140160180200 ppm
13C/DEPT
1H NMR
MASS
IR
% o
f B
ase
Peak
m/z110100908070605040
50
10041
5568
84
97
112
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e
856941
1161
13421454
1701
28582927
13C/DEPT NMR 75.5 MHz
1H NMR 300 MHz
44913_08_p381-425 11/23/04 3:29 PM Page 382
STUDENT EXERCISES
Problem 8.14
1.52.02.53.03.54.04.55.05.56.0 ppm
406080100120140160180200 ppm
13C/DEPT
1H NMR
MASS
17401750 Hz
IR
640 Hz 290300 Hz560570 Hz
% o
f B
ase
Peak
m/z1401301201101009080706050
50
100
5467
82
95123
138
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e
525
903
1246
1381
1670
28702958
13C/DEPT NMR 75.5 MHz
1H NMR 300 MHz
44913_08_p381-425 11/23/04 3:30 PM Page 395
Problem 8.21
1.01.52.02.53.03.5 ppm
406080100120140160180200 ppm
13C/DEPT
1H NMR
MASS
IR
% o
f B
ase
Peak
m/z150
50
100
187
159
15010050
50
100
x 20
15810385
57
43
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e
2962
17201651
1319
1149
1034
CI Reagent gas methane
m/z
13C/DEPT NMR 75.5 MHz
1H NMR 300 MHz
44913_08_p381-425 11/23/04 3:30 PM Page 402
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
ase
Peak
m/z
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e
702760
1092
12151304
1442
16161678
2954
3190
1501401301201101009080706050
50
100
5365
92120
152
3A
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 Hz11201140 Hz
38003820 Hz
13C/DEPT NMR 150.9 MHz
% o
f B
ase
Peak
m/z1601501401301201101009080706050
50
100
164
1491311211039177
6555
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mitt
ance
3514
301629352850
159715121427
1265
1153
1034
856791
4A
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
ase
Peak
m/z
4000 3000 2000 1000Wavenumber (cm-1)
70
80
90
100
%T
rans
mit
tanc
e
3286
16351597
1442
1281
1149
702
20015010050
50
100198
121
105937765
13C/DEPT NMR 150.9 MHz
9A
1.54
1.59
1.61
3.49
3.82
3.85
4.03
4.06
6.71
6.77
6.78
6.79
6.82
7.26
6.71
6.77
6.78
6.79
6.82
2.00
0.36
1.67
1.64
0.32
3.49
3.82
3.85
3.88
5.96
5.89
0.28
0.95
1.54
1.59
1.61
3.26