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112 Problem 2.

Problem 2.3 Spectrum A

Problem 2.3 Spectrum B

Problem 2.3 Spectrum C


Problem 2.3 Spectrum D

Problem 2.4 Spectrum E

Problem 2.4 Spectrum F


Problem 2.4 Spectrum G

Problem 2.4 Spectrum H

Problem 2.4 Spectrum I


Problem 2.5 Spectrum J

Problem 2.5 Spectrum K

Problem 2.5 Spectrum L


Problem 2.5 Spectrum M

Problem 2.6 Spectrum N

Problem 2.6 Spectrum O


Problem 2.6 Spectrum P

Problem 2.6 Spectrum Q

Problem 2.6 Spectrum R


Problem 2.7 Spectrum S

Problem 2.8 Spectrum T


Chapter 8 Additional Problems 1 1
MASS
45
CI Reagent gas methane
100

169
63

171
100

195
50 75 139

197
89 107
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
51 141
65 98 111 153

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
Chapter 8 Additional Problems 4A 5
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


Chapter 8 Additional Problems 4B 6

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
Chapter 8 Additional Problems 5A 8

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


Chapter 8 Additional Problems 5B 9

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
Chapter 8 Additional Problems 6A 10

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
C/DEPT NMR 150.9 MHz

31.0 30.5 ppm

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


Chapter 8 Additional Problems 6B 11

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
Chapter 8 Additional Problems 6C 12

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
Chapter 8 Additional Problems 7A 13
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


Chapter 8 Additional Problems 7B 14

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
Chapter 8 Additional Problems 7C 15

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
Chapter 8 Additional Problems 8A 16
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
Chapter 8 Additional Problems 8B 17

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
Chapter 8 Additional Problems 8C 18

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
Chapter 8 Additional Problems 9A 19

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
Chapter 8 Additional Problems 9B 20

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
Chapter 8 Additional Problems 9C 21

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
Chapter 8 Additional Problems 10A 22
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


Chapter 8 Additional Problems 10B 23

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
Chapter 8 Additional Problems 10C 24

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
Chapter 8 Additional Problems 11A 25

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
C/DEPT NMR 150.9 MHz

30.2 30.1 ppm


30.2 30.1 ppm

200 180 160 140 120 100 80 60 40 20 ppm


Chapter 8 Additional Problems 11B 26

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
Chapter 8 Additional Problems 11C 27

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
Chapter 8 Additional Problems 12A 28

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
C/DEPT NMR 150.9 MHz

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


Chapter 8 Additional Problems 12B 29

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
Chapter 8 Additional Problems 12C 30

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