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Chapter 8 Additional Problems 1
2.83.03.23.43.63.84.04.24.44.64.8 ppm
45505560657075 ppm
13C/DEPT
1H NMR
MASS
IR m/z
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mitt
ance
663
1126
1304
1458
2877
3440
10050
50
100
45
63
75 89 107137139
200190180170
50
100
169
171
195
197
CI Reagent gas methane
13C/DEPT NMR 75.5 MHz
1H NMR 300 MHz
1
Chapter 8 Additional Problems 2
23456789 ppm
20406080100120140160180 ppm
MASS
IR
1H NMR 600 MHz
13C/DEPT NMR 150.9 MHz
% o
f B
ase
Peak
m/z 100500
50
100 41
51
55
65
70 81
83
97
98 111
150140130120110
50
100
113
141 153
m/z
CI Reagent gas methane
4000 3000 2000 1000Wavenumber (cm-1)
80
90
100
%T
rans
mit
tanc
e
29542931
2870 1712
1458
11491103
670680 Hz18701880 Hz 17901800 Hz 390400410420430440 Hz
13C/DEPT NMR 75.5 MHz
1H NMR 300 MHz
2
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 4
4567891011ppm ppm
4
5
6
7
8
9
10
4
5
6
7
8
9
10
ppm
4567891011 ppm
60
80
100
120
140
160
60
80
100
120
140
160
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
3B
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 6
2.02.53.03.54.04.55.05.56.06.57.0ppm ppm
2
3
4
5
6
7
2
3
4
5
6
7
ppm
2.02.53.03.54.04.55.05.56.06.57.0 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
4B
Chapter 8 Additional Problems 7
ppm
6.06.57.0 ppm
105
110
115
120
125
130
135
140
145
150
3.94.0 ppm 1.81.9 ppm
6.06.57.0ppm ppm
20
30
40
50
3.94.0 ppm 1.81.9 ppm
HMQC 600 MHz
F1
F2
4C
Chapter 8 Additional Problems 8
1.52.02.53.03.54.04.55.05.56.0 ppm
2030405060708090100110120130140 ppm
MASS
IR
1500 Hz 600620 Hz17401760 Hz
% o
f B
ase
Peak
m/z15010050
50
100
168140125
111
9783
705541
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mitt
ance
3078
29242854
1643
1466
910
260280 Hz
13C NMR 75.5 MHz
1H NMR 300 MHz
2030405060708090100110120130140 ppm
29.029.229.429.629.8 ppm
13C/DEPT NMR 75.5 MHz
5A
Chapter 8 Additional Problems 9
1.01.52.02.53.03.54.04.55.05.56.06.5ppm ppm
1
2
3
4
5
6
1
2
3
4
5
6
ppm
20406080100120140 ppm
1
2
3
4
5
6
1
2
3
4
5
6
F2
F2
F1
F1
COSY 300 MHz
HETCO 300 MHz
5B
Chapter 8 Additional Problems 10
2.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130140150 ppm
MASS
11001150120012501300 Hz
IR
% o
f B
ase
Peak
m/z140130120110100908070605040
50
100
53
68
77
79
93
107 121
136
4000 3000 2000 1000Wavenumber (cm-1)
100
%T
rans
mit
tanc
e795
887
13731442
1643
2924
3078
85090095010001050 Hz
30.531.0 ppm
1H NMR 600 MHz
13C/DEPT NMR 150.9 MHz
6A
Chapter 8 Additional Problems 11
1.52.02.53.03.54.04.55.05.5ppm ppm
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
ppm
1.52.02.53.03.54.04.55.05.5 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
ppm
1.61.82.02.2 ppm
20
25
30
35
40
45
ppm
1.61.82.02.2 ppm
1.6
1.8
2.0
2.2
6B
Chapter 8 Additional Problems 12
1.41.51.61.71.81.92.02.1 ppm
F2
F1
HMBC 600 MHz
4.85.05.25.45.6ppm
ppm
20
25
30
35
40
ppm
4.85.05.25.45.6 ppm
110
115
120
125
130
135
140
145
150
1.41.51.61.71.81.92.02.1 ppm
6C
Chapter 8 Additional Problems 13
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm
406080100120140160180200 ppm
MASS
IR
1H NMR 600 MHz
13C/DEPT NMR 600 MHz
% o
f B
ase
Peak
m/z
4000 3000 2000 1000Wavenumber (cm-1)
50
100
11341211128813731450
16121682
28702924
1501401301201101009080706050
50
10041
53
6781
109
123137
152
13C/DEPT NMR 150.9 MHz
7A
Chapter 8 Additional Problems 14
1.01.21.41.61.82.02.22.42.62.83.0ppm ppm
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
ppm
1.01.21.41.61.82.02.22.42.62.83.0 ppm
20
25
30
35
40
45
50
20
25
30
35
40
45
50
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
7B
Chapter 8 Additional Problems 15
F2
F1
HMBC 600 MHz
ppm
0.81.01.21.41.61.82.02.22.42.62.8 ppm
150
200
0.81.01.21.41.61.82.02.22.42.62.8ppm ppm
21
22
23
24
25
26
27
28
29
30
31
32
33
ppm
50
52
7C
Chapter 8 Additional Problems 16
2.53.03.54.04.55.05.56.06.57.0 ppm
30405060708090100110120130140150160170180 ppm
MASS
IR
1H NMR 600 MHz
13C/DEPT NMR 600 MHz
42204230 Hz 14101420 Hz36603670 Hz
% o
f B
ase
Peak
m/z120110100908070605040
50
100
124
109
815343
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e
3124
2924
1674
1520
1296
1026
802
13C/DEPT NMR 150.9 MHz
8A
Chapter 8 Additional Problems 17
2.02.53.03.54.04.55.05.56.06.57.07.5ppm ppm
2
3
4
5
6
7
2
3
4
5
6
7
ppm
2.02.53.03.54.04.55.05.56.06.57.07.5 ppm
20
40
60
80
100
120
140
20
40
60
80
100
120
140
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
8B
Chapter 8 Additional Problems 18
2.32.4 ppm
2.32.4 ppm
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
F2
F1
HMBC 600 MHz
6.26.46.66.87.07.2ppm
6.26.46.66.87.07.2 ppm
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
8C
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
Chapter 8 Additional Problems 20
6.66.87.07.27.47.67.88.0ppm ppm
6.6
6.8
7.0
7.2
7.4
7.6
7.8
6.6
6.8
7.0
7.2
7.4
7.6
7.8
ppm
6.66.87.07.27.47.67.88.0 ppm
115
120
125
130
135
140
115
120
125
130
135
140
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
9B
Chapter 8 Additional Problems 21
ppm
128
130
132
134
136
138
F2
F1
HMBC 600 MHz
ppm
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0 ppm
180
200
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0ppm ppm
115
120
9C
Chapter 8 Additional Problems 22
1.82.02.22.42.62.83.03.23.43.63.84.04.24.4 ppm
406080100120140160180200 ppm
MASS
IR
1H NMR 600 MHz
13C/DEPT NMR 600 MHz
26802700 Hz
% o
f B
ase
Peak
m/z140130120110100908070605040
50
100
43
55 69 79
97
140
4000 3000 2000 1000Wavenumber (cm-1)
50
100
%T
rans
mit
tanc
e764
1072
1358
16821720
28542924
25202540 Hz
13C/DEPT NMR 150.9 MHz
10A
Chapter 8 Additional Problems 23
2.02.53.03.54.04.5ppm ppm
2.0
2.5
3.0
3.5
4.0
4.5
2.0
2.5
3.0
3.5
4.0
4.5
ppm
2.02.53.03.54.04.5 ppm
20
30
40
50
60
70
80
90
20
30
40
50
60
70
80
90
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
ppm
1.82.02.2 ppm
18
20
22
24
26
28
1.71.81.92.02.1ppm ppm
1.7
1.8
1.9
2.0
10B
Chapter 8 Additional Problems 24
ppm
90
100
110
120
130
140
150
F2
F1
HMBC 600 MHz
ppm
2.02.53.03.54.04.5 ppm
210
215
2.02.53.03.54.04.5ppm ppm
20
25
10C
Chapter 8 Additional Problems 25
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9 ppm
200 180 160 140 120 100 80 60 40 20 ppm
MASS
IR
910111213 ppm
13C/DEPT NMR 150.9 MHz
1H NMR 600 MHz
% o
f B
ase
Peak
m/z
4000 3000 2000 1000Wavenumber (cm-1)
80
90
100
%T
rans
mitt
ance
949
1188
1404
17051728
2962
3178
15010050
50
100
x 2043
69 71
83
98
114 125
166
169 18
4
x64
30.130.2 ppm
30.130.2 ppm
11A
Chapter 8 Additional Problems 26
1.01.21.41.61.82.02.22.42.62.83.0ppm ppm
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
1.0
1.2
1.4
1.6
1.8
2.0
2.2
2.4
2.6
2.8
ppm
1.01.21.41.61.82.02.22.42.62.83.0 ppm
15
20
25
30
35
40
45
50
55
15
20
25
30
35
40
45
50
55
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
ppm
1.21.41.61.82.02.22.4 ppm
30.0
30.5
11B
Chapter 8 Additional Problems 27
0.81.01.21.41.61.82.02.22.42.62.83.03.2ppm ppm
20
25
30
35
40
45
50
55
F2
F1
HMBC 600 MHz
ppm
0.81.01.21.41.61.82.02.22.42.62.83.03.2 ppm
180
190
200
210
11C
Chapter 8 Additional Problems 28
1.52.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130 ppm
MASS
IR
% o
f B
ase
Peak
m/z
4000 3000 2000 1000Wavenumber (cm-1)
100
%T
rans
mit
tanc
e825
980
113413731450
28702924
2993
1401301201101009080706050
50
100
53 65
7779
93
105
121
136
0.91.01.11.21.31.41.51.61.71.81.9 ppm
13C/DEPT NMR 150.9 MHz
1H NMR 600 MHz
12A
Chapter 8 Additional Problems 29
1.01.52.02.53.03.54.04.55.05.56.0ppm ppm
1
2
3
4
5
1
2
3
4
5
ppm
1.01.52.02.53.03.54.04.55.05.56.0 ppm
20
40
60
80
100
120
20
40
60
80
100
120
F2
F2
F1
F1
HMQC 600 MHz
COSY 600 MHz
ppm
1.01.52.02.5 ppm
15
20
25
30
0.81.01.21.41.61.82.0ppm ppm
1.0
1.5
12B
Chapter 8 Additional Problems 30
0.81.01.21.41.61.82.0 ppm
F2
F1
HMBC 600 MHz
5.65.7ppm
ppm
16
18
20
22
24
26
28
30
ppm
67 ppm
120
130
1400.81.01.21.41.61.82.0 ppm
12C
