Page 1
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
Page 2
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
Page 3
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
Page 4
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
Page 5
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
Page 6
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
Page 7
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
Page 8
6.71
6.77
6.78
6.79
6.82
2.00
0.36
1.67
1.64
0.32
Page 9
3.49
3.82
3.85
3.88
5.96
5.89
0.28
0.95
Page 10
1.54
1.59
1.61
3.26