ch08 Solutions

CHAPTER 8 ASSIGNED PROBLEMS
Problem 8.1
MASS
68
55
% of Base Peak 100
41 112
84
50
97
40 50 60 70 80 90 100 110
m/z
IR O
100
1 2
3
%Transmittance
4
50 Cycloheptanone
C7H12O
Mol. Wt.: 112
2927
2858
1701
1454
1342
1161
941
856
4000 3000 2000 1000
Wavenumber (cm-1)
11 4
HHNMR
NMR 300 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 ppm
1313
C/DEPT NMR 75.5 MHz
C/DEPT
2 4 3
200 180 160 140 120 100 80 60 40 ppm

MASS Problem 8.2
124
% of Base Peak 100
94
50 95
81
53 66
50 60 70 80 90 100 110 120

m/z
IR
OH
100
3
4 2
%Transmittance
50 5 1
7
6 OCH3
m-Methoxyphenol
C 7H 8 O 2
3398
3005
2947
2839
1601
1493
1284
1149
1041
945
837
768
687
Mol. Wt.: 124
4000 3000 2000 1000

Wavenumber (cm-1)
11 7
H NMR
H NMR 300 MHz 2
5 6
4
2150 2140 Hz 1960 1950 Hz 1930 1920 Hz

OH
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 ppm
13
13
C/DEPT NMR 75.5 MHz
C/DEPT
4
3 2 7
1 5
3
1
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
Problem 8.3
MASS
55
% of Base Peak M-1
100
83
39 41
M
50 53 84
65 66
40 45 50 55 60 65 70 75 80 85
m/z
IR
100
%Transmittance
50
3332
2978
2939
2877
2291
2229
1454
1319
1227
1138
1014
741
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz
5
1
4
1280 1260 Hz 680 660 Hz OH
4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
HO
4
H 2C C C CH2
1 2 3
5 CH3
CDCl3 2-Pentyn-ol
3 C5 H 8 O 5
Mol. Wt.: 84
4
1
2 78.0 77.5 77.0 76.5 ppm
95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm
Problem 8.4
MASS
75
CI Reagent gas methane
% of Base Peak x 30
100 111
110
100 113
49 112 M 146
61 77 99 148
50 97 75 150
148 50
114 77 115
146 152
50 100 150 100 m/z 150

m/z
IR Cl
100
Cl 1 CH 3 Cl
CH2 2 CH2
90
%Transmittance
80
1,2,3-Trichloropropane
70 C3H5Cl3
Mol. Wt.: 146
3016
2962
1435
1288
1219
910
717
663
4000 3000 2000 1000
1 Wavenumber (cm-1) 1+3
1H
H NMR
NMR 300 MHz
4.35 4.30 4.25 4.20 4.15 4.10 4.05 4.00 3.95 3.90 3.85 3.80 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
1+3
75 70 65 60 55 50 45 ppm
Problem 8.5
MASS
m/z %M 111
126 (M) 100.0
% of Base Peak 100 127 (M+1) 8.2
128 (M+2) 4.9 126
50 39
43 83
49 57
40 50 60 70 80 90 100 110 120 130

IR m/z
100
%Transmittance
50
3089
1662
1415
1273
1061
933
856
725
590
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz
3 1 6
2
2300 2280 Hz 2140 2120 Hz

4 5
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
13
13 C/DEPT
C/DEPT NMR 75.5 MHz 2 3
1
O
S 4
5
6 CH3
Ethanone, 1-(2-thienyl)-
2 2-Acetylthiophene
1 3
C6H6OS 6
Mol. Wt.: 126
5 4
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
Problem 8.6
MASS
% of Base Peak
105 x 10
100
186
184
50 51 77
50 100 150
IR m/z
100
90
%Transmittance
80
70
3032
2985
1496
1450
1211
964
764
694
594
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 300 MHz 2 6
3 4
1590 1580 1570 Hz
2260 2250 2240 2230 2220 2210 2200 Hz

5 640 630 620 Hz
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
13
C/DEPT NMR 75.5 MHz
H3C 5 Br
6
1
2
3
4
(1-Bromoethyl)benzene
4 C8H9Br
3 2 Mol. Wt.: 184
6
5
1
140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.7
MASS
109
% of Base Peak 124
100 81
53
50
63
75
50 60 70 80 90 100 110 120

m/z
IR
100
%Transmittance
50
3348
2951
2835
1859
1701
1612
1512
1234
1034
825
733
513
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz
5
2 3
OH
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 ppm
13
13
C/DEPT OH
C/DEPT NMR 75.5 MHz
4
3
2
1
OCH3
5
3 2 p-Methoxyphenol
C 7H 8 O 2 5
Mol. Wt.: 124
1 4
150 140 130 120 110 100 90 80 70 60 50 ppm

Problem 8.8
MASS
128
% of Base Peak 100
64
130
50 92
73
50 60 70 80 90 100 110 120 130

m/z
IR
100
%Transmittance
50
3521
3464
3074
3039
1585
1481
1454
1338
1200
1030
748
679
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz OH
6 4 1
3 2 Cl
6
5
3 OH
5
4
o-Chlorophenol
C6H5ClO
Mol. Wt.: 128
7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
5 4
3 6
1 2
155 150 145 140 135 130 125 120 115 ppm
Problem 8.9
MASS
% of Base Peak 55 x 20
87 115
100 196
73 194
50 135 137 163 165
0
50 100 150
m/z
IR
100
%Transmittance
50 2954
1736
1435
1365
1203
748
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
O
6 6
4
Br 5 3 1 O
2
5 Methyl 5-bromo valerate 2

C6H11BrO2
Mol. Wt.: 194 3
4
3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
5 2
4
3
6
1 33.0 32.5 32.0 ppm
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.10
MASS
54
% of Base Peak 100 67 84
93
50
111 126
50 60 70 80 90 100 110 120

m/z
IR
100
%Transmittance
3344
2958
2931
2873
1466
1331
1045
849
4000 8 3000 4 2000 1000
1 7 Wavenumber
5 2 1 OH
(cm-1)
1H 6
H NMR
NMR 300 MHz 3
8
3-Octyn-1-ol
C8H14O
Mol. Wt.: 126 6
1 7
2 5
OH
3.5 3.0 2.5 2.0 1.5 1.0 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
1 6
5 8
7
2
84 82 80 78 ppm
4 3
85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm
MASS Problem 8.11
162
% of Base Peak 100
164
63
98
50
73 126
128
50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR
100
%Transmittance
50
3521
3097
1585
1477
1404
1277
1188
814
725
555
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
3 OH
6
1
2 Cl
6
5
5 3
OH
4
Cl
2,4-Dichlorophenol
C6H4Cl2O
Mol. Wt.: 162
7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
3 5 6
1
4 2
155 150 145 140 135 130 125 120 115 ppm
Problem 8.12
MASS 123
% of Base Peak
100 95
75
50 138
50 63
50 60 70 80 90 100 110 120 130 140

IR m/z
100
%Transmittance
50
3356
3074
3005
1685
1597
1358
1265
1157
960
841
567
4000 3000 2000 1000
Wavenumber (cm-1)
19
1
H NMR 300 MHz F NMR 282.4 MHz
1
2 3 H Coupled
6
1
H Decoupled
2400 2390 2380 Hz 2140 2130 Hz
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm -104.4 -104.5 ppm
13 5 6
C/DEPT NMR 75.5 MHz COCH3
1
2
3
4
F
2 3 4-Fluoroacetophenone
C8H7FO 6
Mol. Wt.: 138
4 130 128 126 124 122 120 118 ppm
5
1
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
Problem 8.13
MASS
96
% of Base Peak 100
50 70
50 75 77
50 55 60 65 70 75 80 85 90 95
IR m/z
100 F
1
2
%Transmittance
3
4
95
Fluorobenzene
C 6H 5 F
3749
3062
1697
1604
1504
1234
756
Mol. Wt.: 96
4000 3000 2000 1000
Wavenumber (cm-1)
11HNMR 300 MHz 19
H NMR F NMR 282.4 MHz
1
H Coupled
2
3
4
7.4 7.3 7.2 7.1 ppm -80.1 -80.2 -80.3 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
3 2
4
130 128 126 124 122 120 118 116 ppm
1
165 160 155 150 145 140 135 130 125 120 115 ppm
Problem 8.14
MASS
82
% of Base Peak 100
50 138
54
67 95
123
50 60 70 80 90 100 110 120 130 140

IR m/z
100
%Transmittance
50
2958
2870
1670
1381
1246
903
525
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz 6 89
7
4
1750 1740 Hz 640 Hz 570 560 Hz 300 290 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/DEPT NMR 75.5 MHz 7
CH3
3
4 2
9
H 3C 5 1
6 O
H3 C
8 89
Isophorone
C9H14O
2 6 4
Mol. Wt.: 138 7
1 3 5
200 180 160 140 120 100 80 60 40 ppm

Problem 8.15
MASS
54
% of Base Peak
50 68
149
81 147
107 109
79 93 95 119 121
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
90
%Transmittance
80
70
2970
2245
1435
1250
756
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz 2
4 3 1
Br 4 2
N 3
4-Bromobutanoyl nitrile
C4H6BrN
Mol. Wt.: 147
3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
3 2
120 110 100 90 80 70 60 50 40 30 20 ppm

Problem 8.16
MASS
106
% of Base Peak 100
50 137
77
50 60 70 80 90 100 110 120 130 140

m/z
IR
100
%Transmittance
90
80
3348
3194
2931
1620
1512
1442
1049
825
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
6
3
2 OH
5 4 3 2 ppm 5
7.5 7.0 6.5 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 OH
C/DEPT NMR 75.5 MHz
6
5
1
OH
2
3
2 3 4
NH2 6 5
p-Aminophenylethanol
C8H11NO
4 1 Mol. Wt.: 137
140 130 120 110 100 90 80 70 60 50 40 ppm

Problem 8.17
MASS
119
% of Base Peak 100
50 91
64
76
50 60 70 80 90 100 110 120

m/z
IR
100
90
%Transmittance
80
70
3309
2245
1589
1481
1342
787
671
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
2 3
OH
7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
2 3
5 1 4
N C OH
p-Cyanophenol
C7H5NO
Mol. Wt.: 119 2 3
4 5 1
165 160 155 150 145 140 135 130 125 120 115 110 ppm
Problem 8.18
MASS
163
% of Base Peak 100
50 178
77 91 135
50 100 150
m/z
IR
100
%Transmittance
50
3572
2962
2870
1458
1203
1149
748
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz 6
3 2150 2100 Hz 1000 950 Hz 450 400 Hz

4 OH
5
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz 6
OH
1 5
2
6
3
4
2,6-Diisopropyl phenol 6
C12H18O
3 Mol. Wt.: 178 5
4
1 2
150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

Problem 8.19
MASS
106
% of Base Peak 78 121
100
51
50
50 60 70 80 90 100 110 120

m/z
IR
100
%Transmittance
50
3363
3047
1689
1419
1273
957
702
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H 4
H NMR
NMR 300 MHz 2 3
7
5
2720 2700 Hz 2600 2580 Hz 2440 2420 Hz 2200 2180 Hz
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm
13 3
13C/DEPT
C/DEPT NMR 75.5 MHz 4 2
7
5 1
6 CH3
N C
O
2-Acetylpyridine
5 4 3 2 C7H7NO 7
Mol. Wt.: 121
6 1
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
Problem 8.20
MASS
108
123
% of Base Peak 100
50 53 80
40 50 60 70 80 90 100 110 120

m/z
IR
100
%Transmittance
50
3109
2947
1651
1404
1095
741
633
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz 7
5
2060 Hz 2020 Hz 1820 Hz

4 3 2
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
3
2
4 7
1
6 CH3
N
H3C5 O
4 2 3
1-Methyl-2-acetylpyrrole 7
1 C7H9NO 5
Mol. Wt.: 123
6
180 160 140 120 100 80 60 40 ppm

Problem 8.21
MASS
% of Base Peak x 20
43 159
100 100
85
57 103 158
50 50
187
50 100 150 150 m/z

m/z
IR
100
%Transmittance
50
2962
1720
1651
1319
1149
1034
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz
7
1
3
5
6
3.5 3.0 2.5 2.0 1.5 1.0 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
7
1 6
2 4 O 5
3 7
O O
Isobutylacetoacetate 7
C8H14O3 5 3 6
Mol. Wt.: 158 1
2 4
200 180 160 140 120 100 80 60 40 ppm

Problem 8.22
MASS
119
% of Base Peak 100
50 91
64
76
50 60 70 80 90 100 110 120

m/z
IR
100
90
%Transmittance
80
70
3309
2245
1589
1481
1342
787
671
4000 3000 2000 1000
11
Wavenumber (cm-1)
H NMR 600
300 MHz OH
42 3
4 2
5 6
1
5 7
C
6 N OH
m-Cyanophenol
C7H5NO
Mol. Wt.: 119
7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 ppm
13
13 C/DEPT NMR 600
75.5MHz
MHz
C/DEPT NMR
6 4 2
5
3
1
7
155 150 145 140 135 130 125 120 115 ppm
Problem 8.23
MASS
x 20
183 185
% of Base Peak
264
100 262
200 224 226 260
198
75 155 157
50
100 150 200 250

IR m/z
100
%Transmittance
50
3356
3089
3059
2962
1685
1585
1485
1396
1223
1068
995
810
617
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
6 8 5
3
2
7.9 7.8 7.7 7.6 ppm 3.6 3.4 3.2 3.0 2.8 2.6 2.4 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz 5 6 7 8
COCH2CH2CH2Cl
1
2
3
4
3 2
Br 6 7 8
4’Bromo-4-chlorobutyrophenone
5 C10H10BrClO
Mol. Wt.: 260
1 4
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
Problem 8.24
MASS 100
% of Base Peak
100 55 147
74
50 69
83 128 50
175 187
50 100 150 150 200

m/z
m/z
IR
100
%Transmittance
50
3039
2978
2669
1709
1466
1419
1277
1238
930
4000 3000 2000 1000
1 Wavenumber (cm-1)
1H
H NMR
NMR 300 MHz
4 6
2x OH
x64
3
2
12 11 ppm 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
13
13C/DEPT
C/DEPT NMR 75.5 MHz
O O
3
2 CH2 C 5
HO 1 CH CH2 OH
4
CH3
6
2 6
4 3
2-Methyl glutaric Acid
C6H10O4
15 Mol. Wt.: 146
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm
Problem 8.25
MASS
91
% of Base Peak
92
93
100
66
100
50
51
50
50 60 70 80 90 80 90
m/z m/z
IR
100
90
%Transmittance
80
3055
2962
1720
1342
1065
802
725
4000 3000 2000 1000
Wavenumber (cm-1)
1
H NMR 300 MHz 3
2
1
2050 2040 Hz 1090 1080 Hz 615 610 605 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 75.5 MHz
2 1
Bicyclo[2,2,1] hepta-2-5-diene 3
1 C7 H 8 2
Mol. Wt.: 92
140 130 120 110 100 90 80 70 60 50 ppm

Problem 8.26
MASS M
156
% of Base Peak 100
63 M+2
158
50
98 121
50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR
100
586
%Transmittance
50 2900
933
802
1041
1234
1473
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
6
3 7
4
6.85 6.80 6.75 6.70 6.65 ppm 6.00 5.95 ppm

1313
C/DEPT
C/DEPTNMR
NMR600 MHz
150.9 MHz
3
2 O
4
7
5
1 O
Cl 6
5-chloro-1,3-benzodioxole
C7H5ClO2 4
Mol. Wt.: 156 36 7
1 2 5
155 150 145 140 135 130 125 120 115 110 105 ppm
Problem 8.27A
MASS
55
42
% of Base Peak 100
84
50 114
70
40 50 60 70 80 90 100 110
m/z
IR
100
%Transmittance
50
2931
1728
1442
1165
1057
856
571
4000 3000 2000 1000
Wavenumber (cm-1)
11
H
H NMR
NMR 300 MHz O
1
2
6 1 O 2
3 6 4
3 5
4 5
ε-Caprolactone
C6H10O2
Mol. Wt.: 114
4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
13 C/DEPT
C/DEPT NMR 75.5 MHz
43
6 2 5
170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm

Problem 8.27B
ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm COSY 300 MHz
1.5 1.5 4
1 2 3 4 5 6
5
O 3
2.0 2.0
2 1 O
2
2.5 3 6 2.5
F1
4 5
3.0 ε-Caprolactone 3.0
C6H10O2
Mol. Wt.: 114
3.5 3.5
4.0 4.0
6
F2 HETCOR 75.5MHz
MHz
4 3 HETCO 300
6 2 5
ppm
1.5 1.5
2.0 2.0
2.5 2.5
F1
3.0 3.0
3.5 3.5
4.0 4.0
4.5 4.5
65 60 55 50 45 40 35 30 25 ppm
F2
Problem 8.28A
MASS
% of Base Peak 55 x 10 137
69
100 120
82 90 118 5
50 92 139
50 m/z 100 130 140 150

m/z
IR
100
%Transmittance
50
3332
2939
2862
1458
1057
725
648
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
1 6
HO 1 3 5
2 4 6 Cl 2 4 3
5
1-Hexanol-6-chloro
C6H13ClO
Mol. Wt.: 136
OH
3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 ppm
1313
C/DEPT C/DEPTNMR
NMR600 MHz
150.9 MHz
5 2 4 3
1 6
60 55 50 45 40 35 30 25 ppm
Problem 8.28B
ppm 3.5 3.0 2.5 2.0 1.5 ppm COSY 600 MHz
1.5 1.5
2.0 2.0
HO 1 3 5
2 4 6 Cl
F1 1-Hexanol-6-chloro
2.5 C6H13ClO 2.5
Mol. Wt.: 136
3.0 3.0
3.5 3.5
1 6 F2 HMQC 600 MHz

OH 5 2 4 3
ppm
25 25 3
4
OH
30 30
35 35
40 5 2 40
F1 6
45 ppm 45
50 32 50
55 55
60 33 60
2.0 1.8 1.6 1.4 ppm 1
3.5 3.0 2.5 2.0 1.5 ppm

F2
Problem 8.29A
MASS
95
% of Base Peak 100
45 67 69
50 55 110 128
81 113
50 60 70 80 90 100 110 120 130

m/z
IR
100
%Transmittance
50
3344
2966
2924
1450
1377
1126
1041
825
4000 3000 2000 1000
Wavenumber (cm-1)
11
HNMR
H NMR 300 MHz 1
7 8
1540 Hz 1140 Hz 500 480 Hz 440 Hz 3

5 2 4 OH
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm
13
13
C/DEPT NMR 75.5 MHz
C/DEPT
7
OH
5 3
6 4 2 1
8 1 3 4
5 2 8
6-Methyl-5-hepten-2-ol
C8H16O 7
6 Mol. Wt.: 128
130 120 110 100 90 80 70 60 50 40 30 20 ppm

Problem 8.29B
ppm 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 300 MHz
1.0 1.0
1
1.5 1.5 3
7
OH 8
2.0 2.0 4
2.5 2.5
F1 3.0 3.0
3.5 3.5
2
4.0 4.0
4.5 4.5
5.0 5.0
5
5 F2 2 3 84 1 HETCOR300
75.5 MHz
7 HETCO MHz
ppm
1.0
7
1.5 OH
5 3
6 4 2
2.0 8 1
6-Methyl-5-hepten-2-ol
2.5 C8H16O
Mol. Wt.: 128
3.0
F1
3.5 OH
4.0
4.5
5.0
5.5
120 100 80 60 40 20 ppm
F2
Problem 8.30A
MASS
88
% of Base Peak 100
225
223
69 100
50
253
251
263
265
143 177 179
159 194
50
0
50 100 m/z 150 230 240 250 260
m/z
IR
100
%Transmittance
50
2939
2870
1736
1458
1188
1034
4000 3000 2000 1000
11 Wavenumber (cm-1)
H
H NMR
NMR 300
600 MHz
MHz 8
6
7 2
5 3 4
4.0 3.5 3.0 2.5 2.0 1.5 ppm

13
13 C/DEPTNMR 75.5
C/DEPT NMR 600 MHz
MHz
5 3 1 O 7
6 4 2 8 4 3
Br 2,6,5
O 7 8
Ethyl 6-Bromohexanoate
1 C8H15BrO2
Mol. Wt.: 222
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.30B
ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 300 MHz
1.0 1.0
8
4
1.5 1.5 3
5
2.0 2.0
2
F1
2.5 2.5
1
1
3.0 3.0
6
3.5 3.5
4.0 4.0 7
7 F2 2 6 5 4 3 8 HETCOR
HETCO75.5
300MHz
MHz
ppm
1.0 1
1.0
5 3 O 7 8 8
Br 6 4 2
4
1.5 O 1.5 3
Ethyl 6-Bromohexanoate 5
C8H15BrO2
2.0 Mol. Wt.: 222 2.0
2
F1 2.5 2.5
3.0 3.0
6
3.5 3.5
4.0 4.0 7
60 55 50 45 40 35 30 25 20 15 ppm
F2
Problem 8.31A
MASS
134
% of Base Peak 100
41
94
119
50 65 91
77 105
40 50 60 70 80 90 100 110 120 130

m/z
IR
100
%Transmittance
50
3066
3032
2916
2866
1601
1496
1242
752
690
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
5
2
3
4 3680 3660 Hz 3300 3280 Hz 3220 3200 Hz 2760 2740 Hz

6 7
7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 ppm
13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
5 6 7
OCH2CH=CH2
1
2
3 2 3
4
4 Allylphenyl ether 5
7 C9H10O
6
1 Mol. Wt.: 134
160 150 140 130 120 110 100 90 80 70 ppm

Problem 8.31B
ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 ppm COSY 600 MHz
4.5 4.5
5.0 5.0
5.5 5.5
F1
6.0 6.0
6.5 6.5
7.0 7.0
2
3 4 F2 5 HMQC 600 MHz
6 7
ppm
5 6 7
70 OCH2CH=CH2 70 5
1
80 2 80
3
90 90
4
Allylphenyl ether
100 C9H10O 100
Mol. Wt.: 134
F1 110 diastereotopic 110
2
7
120 120 4
130 130 3
6
140 140
150 150
1
7.5 7.0 6.5 6.0 5.5 5.0 4.5 ppm
F2
Problem 8.32A
MASS
% of Base Peak
95 x 20
100
110 139
50 55 67 154
109 121 136
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
%Transmittance
50
3317
2951
2877
1712
1365
1227
1057
829
4000 3000 2000 1000
1
Wavenumber
3 (cm-1)
H NMR 600 MHz 8
9 10
OH
2400 Hz 1350 Hz 1150 Hz 1050 Hz 950 Hz 750 Hz 550 Hz 500 Hz

2 In the above insets each tick mark is 10 Hz 3 6 5 4 5 6 3
4.0 3.5 3.0 2.5 2.0 1.5 ppm

13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
10 9
H 3C CH3
8
7
CH3
6
1 2
5 4 3 OH 3 5 6 9 10 8
Borneol 4
2
C10H18O
Mol. Wt.: 154
1 7
75 70 65 60 55 50 45 40 35 30 25 20 15 ppm
Problem 8.32B
7
ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
9.10,8
1.0 1.0 3
6
5
1.5 1.5 OH
4
5
6
2.0 2.0
F1 3
10 9
2.5 H 3C CH3 2.5
8
7
CH3
3.0 6 3.0
1 2
5 4 3 OH
3.5 Borneol 3.5
C10H18O
Mol. Wt.: 154
4.0 4.0 2
F2 HMQC 600 MHz

ppm
ppm 8
10
20 20 9
15 6
30 30 5
20
40 diastereotopic 40 3
25
0.90 0.85 ppm
F1 7 4
50 50 1
60 60
70 70
2
4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

F2
Problem 8.33A
MASS
85
% of Base Peak 100
50 57 70
114
50 60 70 80 90 100 110
m/z
IR
100
656
2885
1358
1466
%Transmittance
972
50 2970
1180
1774
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz 6
3 2
6
4 1
O 2
5 O
4 3 3 5 5
γ-Caprolactone
C6H10O2
Mol. Wt.: 114
4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
2 5 3
4 6
1 29 28 ppm
180 160 140 120 100 80 60 40 20 ppm

Problem 8.33B
ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
1.0 1.0 6
1.5 1.5
5
3
2.0 2.0
3
2
F1 2.5 3 2
2.5
6
4 1
3.0 O 3.0
5 O
γ-Caprolactone
3.5 C6H10O2 3.5
Mol. Wt.: 114
4.0 4.0
F2 HMQC 600 MHz

ppm
10 10 6
20 20
30 30
diastereotopic
40 ppm 40
F1 50 3
50
28 5
2
60 60
30
2.5 2.0 1.5 ppm
70 70
80 80
4
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

F2
Problem 8.34A
MASS
41
% of Base Peak 69
100
55 81
95
50 109 123
138 156
40 50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR
100
%Transmittance
50
3332
2924
1450
1381
1057
833
4000 3000 2000 1000
1 10
Wavenumber 9
(cm-1)
1 HO CH3 CH3
H NMR 600 MHz 8
6
7 9
2 3
CH3 10
4 5 8
Citronellol
C10H20O
Mol. Wt.: 156
6 3
1 5 2 4
OH
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
5
9 24 3 8
6 1
7 10
26 25 ppm
130 120 110 100 90 80 70 60 50 40 30 20 ppm

Problem 8.34B
ppm 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
10
1.0 1.0 4
2 3
1.5 1.5 8
OH 9
2.0 2.0 5
2.5 2.5
F1
3.0 3.0
3.5 3.5 1
4.0 4.0
4.5 4.5
5.0 5.0 6
F2 HMQC 600 MHz

ppm
1 10 9 10
HO 20 CH3 CH3 20 8
6 95
7 3
2 3
CH3 4
40 4 5 8 40 2
Citronellol
C10H20O
60 Wt.: 156
Mol. 60 1
ppm
F1 80 80
20
100 100
30
120 40 120
6
2.0 1.5 1.0 ppm 7
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
F2
Problem 8.35A
MASS
95
81
% of Base Peak 100
41
55 69 108
50 152
137
50 60 70 80 90 100 110 120 130 140 150

m/z
IR 9 8
H3C 7 CH3
100
5 4
1273
748
3
%Transmittance
1450
2
1041
6 1
50 O
10CH3
2954
Camphor
1743
C10H16O
Mol. Wt.: 152
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz 8 9 10
4 3
3 5
5 6 6
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 0.9 ppm
13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
4 3 6 5 9 8 10
2
1 7
220 ppm 55 50 45 40 35 30 25 20 15 ppm

Problem 8.35B
ppm 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm COSY 600 MHz
0.6 0.6
0.8 0.8 10
9
1.0 1.0
8
1.2 1.2
5
1.4 1.4
F1 6
1.6 1.6
6
1.8 1.8
3
5
2.0 2.0
4
2.2 2.2
3
2.4 2.4
F2 HMQC 600 MHz

ppm
10 10 10
8
20 20 9
5
30 9 8 30 6
H3C 7 CH3
F1
5 4
3
2
40 6 1 40
4
10CH3 O 3
7
Camphor
50 C10H16O 50
Mol. Wt.: 152
1
2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 ppm
F2
Problem 8.35C
INADEQUATE
INADAQUATE150.9
150.9MHz
MHz
2 1 3
Hz
9 8
-20000 H3C 7 CH3 -20000
-15000 5 4 -15000
3
2
-10000 6 1 -10000
10CH3 O
-5000 -5000
Camphor
F1 0 C10H16O
Mol. Wt.: 152 0
5000 5000
10000 10000
220 200 180 160 140 120 100 80 60 40 20 ppm
F2
Hz
1 7 43 6 5 9 8 10
-25000 -25000
-24000 -24000
-23000 -23000
-22000 -22000
F1
-21000 -21000
-20000 -20000
-19000 -19000
-18000 -18000
-17000 -17000
65 60 55 50 45 40 35 30 25 20 15 10 5 ppm
F2
Problem 8.36A
MASS
100 70
50 55 130
115
40 50 60 70 80 90 100 110 120 130

m/z
IR
100
1466
%Transmittance
2877
1373
1041
2962
50
1242
1743
4000 3000 2000 1000
Wavenumber (cm-1) 7 is doublet
1
H NMR 600 MHz 1
6 is triplet
2350 Hz 2300 Hz 1000 Hz 850 Hz 700 Hz 550 Hz

In the above insets each tick mark is 10 Hz
3
4
5 5
3.5 3.0 2.5 2.0 1.5 ppm

13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
O
3
4 6
H3C 2 O 5 CH3
1 3
7 CH3
5
7 6
2-Methylbuty acetate 4
C7H14O2 1
2
Mol. Wt.: 130
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

Problem 8.36B
ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
6
1.0 1.0
5 7
5
1.5 1.5
4
2.0 2.0 1
F1
2.5 2.5
3.0 3.0
3.5 3.5
3
4.0 4.0
F2 HMQC 600 MHz

ppm
10 10 6
ppm
10
7
6
20 20 1
5
15
30 7 30
4
0.95 0.90 0.85 ppm
40 40
F1
O
50 3 50
4 6
H3C 2 O 5 CH3
1
60 7 CH3 60
2-Methylbuty acetate 3
70 C7H14O2
70
Mol. Wt.: 130
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

F2
Problem 8.37A
MASS
111 m/z %M
151 (M-1) 37.5
% of Base Peak 100 152 (M) 100.0
153 (M+1) 12.7
154 (M+2) 5.2 152
50
69 83
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
3008
3093
%Transmittance
1057
50
957
725
1419
1234
1651
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz 7 and 8 are diastereotopic
78
4680 Hz 4560 Hz 4260 Hz 1520 Hz 740 720 Hz 600 Hz

3 1 2 6
7.5 7.0 6.5 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 NMR
C/DEPT NMR 150.9
600 MHz
MHz
O
S 4 C 6
5 7
1
3 8
2
7 8
cyclopropyl(thiophen-2-yl)methanone
3 C8H8OS
1 2 Mol. Wt.: 152 6
5 4
180 160 140 120 100 80 60 40 20 ppm

Problem 8.37B
ppm 8 7 6 5 4 3 2 1 ppm COSY 600 MHz
1 1 87
2 2
6
3 3
4 4
F1
5 5
6 6
7 7 2
1
8 8 3
F2 HMQC 600 MHz

ppm
78
20 20 6
O
S 4 C 6
5 7
40 1 40
3 8
2
60 cyclopropyl(thiophen-2-yl)methanone 60
C8H8OS
Mol. Wt.: 152
F1
80 80
100 100
120 120
2
3
1
8 7 6 5 4 3 2 1 ppm
F2
Problem 8.38A
MASS
121
% of Base Peak
164
100
103
77
91
136
50
149
65
60 70 80 90 100 110 120 130 140 150 160
m/z
IR
100
2870
663
%Transmittance
949
764
3201
2962
1412
1550
50
1265
1473
1612
4000 3000 2000 1000
Wavenumber (cm-1)
1 9 10
H NMR 600 MHz 8
7 5
3 6
3940 3920 Hz 3880 3860 Hz 3720 Hz 1280 Hz 320 300 Hz
OH
9 8 7 6 5 4 3 2 1 ppm
13
C/DEPT NMR 150.9 MHz O
7 1
2 OH
6
5 3
4
2 1 H 3C 8 CH3
10 9 9 10
6 537 β-Thujaplicin
C10H12O2 8
171.5 171.0 ppm Mol. Wt.: 164
4
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.38B
ppm 7 6 5 4 3 2 1 ppm COSY 600 MHz
ppm 6.8 6.6 6.4 6.2 ppm 9 10

1 1
6.2 5 O
2 2 8
7 1
2 OH
6.4 6
7
3 3
6.6 36 5 3
F1 4
4 4
H 3C 8 CH3
10 9
β-Thujaplicin
5 5
C10H12O2
Mol. Wt.: 164
6 6
7 7
F2 HMQC 600 MHz

ppm
20 20
9 10
40 ppm 40 8
7
125 3
60 60
5
130
F1 80 135
80
6
140
100 6.8 6.6 6.4 6.2 ppm
100
120 120 7
3
5
140 140 6
7 6 5 4 3 2 1 ppm
F2
Problem 8.38C
INADEQUATE 150.9 MHz

INADEQUATE 600 MHz
9
4 8 10
Hz
-20000 -20000
-15000 -15000
-10000 -10000
-5000 -5000
F1 0 0
5000 5000
10000 10000
15000 15000
20000 20000
160 140 120 100 80 60 40 20 ppm

F2
2 1 4 6 5 3 7
Hz
0 0
5000 5000
F1
10000 10000
15000 O 15000
7 1
2 OH
6
20000 20000
5 3
4
H C 8 CH3
175 170 165 160 155 150 3 10
145 140
9 135 130 125 120 115 ppm
F2
β-Thujaplicin
C10H12O2
Mol. Wt.: 164
Problem 8.39A
MASS 123
% of Base Peak
100 83
151
41 55 232
50 69 95 230
110
50 100 150 200

m/z
IR
100
90
1219
1034
1365
1442
1473
%Transmittance
80
70 2954
1751
4000 3000 2000 1000
Wavenumber (cm-1)
1 10
H NMR 600 MHz
8 9
2800 Hz 1350 1300 1250 1200 1150 1100 1050 1000 950 900 850 Hz
3 4 5 5 6 6
4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

9 8
13
C/DEPT NMR 150.9 MHz H3 C CH3
7
4
5 3
2
1 Br
6
CH3 O
10
8 9 3-Bromocamphor
C10H15BrO 6 5
Mol. Wt.: 230 4 10
3
2 20.0 19.9 19.8 ppm 1 7
200 180 160 140 120 100 80 60 40 20 ppm

Problem 8.39B
COSY 600 MHz

ppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
9
1.0 1.0 10
8
1.5 1.5 6
6
2.0 2.0 5
5
4
2.5 2.5
F1
3.0 3.0
3.5 3.5
4.0 4.0
4.5 4.5
3
F2 HMQC 600 MHz

ppm
9 8 10
10 H3 C CH3 10
7
4
5 3 89
20 20
2 5
1 Br
6
CH3 O
10
30 3-Bromocamphor 30 6
F1 C10H15BrO
Mol. Wt.: 230
40 40
7
50 50 4
3
1
60 60
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
F2
Problem 8.39C
INADEQUATE 150.9
INADEQUATE 600MHz
MHz
2 13
Hz
-20000 -20000
-15000 -15000
-10000 -10000
F1
-5000 -5000
0 0
5000 5000
200 180 160 140 120 100 80 60 40 20 ppm

F2
1 3 4 7 6 5 10
Hz
-25000 -25000
-24000 -24000
-23000 -23000
-22000 -22000
9 8
F1 H3 C CH3
-21000 7 -21000
4
5 3
-20000 2 -20000
1 Br
6
-19000 CH3 O -19000
10
3-Bromocamphor
C10H15BrO
-18000 Mol. Wt.: 230 -18000
-17000 -17000
60 55 50 45 40 35 30 25 20 15 10 5 ppm
F2
Problem 8.40A
MASS
FM (found) = 154.1351 154
108
% of Base Peak 100 81
71 111 139
93
55
50
136
50 60 70 80 90 100 110 120 130 140 150

m/z
IR
100
841
%Transmittance
1466
1373
1080
1219
50
987
2970
4000 3000 2000 1000

1
Wavenumber (cm-1)
H NMR 600 MHz 8,9 10
4,6
3,7
3,7 4,6
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
6 10
7 CH3
4 5 O
1
3 2 CH3
8 8,9
9 CH3 4,6 3,77
Cineole
10
C10H18O 2
1 5 Mol. Wt.: 154
75 70 65 60 55 50 45 40 35 30 25 ppm
Problem 8.40B
ppm 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm COSY 600 MHz
10
1.0 1.0
8,9
1.2 1.2
2
1.4 1.4
3,7 4,6
F1
1.6 1.6 4,6
1.8 1.8
2.0 2.0 3,7
1 4 5 6
F2 HMQC 600 MHz

ppm
22 22
3,7
24 7 10 24
6 CH3
5 1
26 O 26
2
3 CH3
4 10
8
F1 28 9 CH3 28
8,9
Cineole
30 C10H18O 30
Mol. Wt.: 154
4,6
32 32
2
34 34
2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm

F2
Problem 8.41A
MASS
82
% of Base Peak
67 CI Reagent gas methane
100 155
54 FM (found) = 155.0711 by CI
100
50
50 183 195
110
50 100 160 170 180 190

m/z m/z
IR
100
1450
%Transmittance
2862
50 2947
1859
1219
903
1790
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz O
3 4
2
4 1
2 O
O 3
1,2-cyclohexanedicarb
oxylic acid anhydride
C8H10O3
Mol. Wt.: 154
3.3 3.2 3.1 3.0 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 ppm
13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
2
3 4
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.41B
ppm 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm COSY 600 MHz
1.5 1.5 4
3
2.0 2.0
F1
2.5 2.5
3.0 3.0
2
F2 HMQC 600 MHz

ppm
4
3
25 25
O
3
30 2 30
4 1
O
F1
35 O 35
1,2-cyclohexanedicarb
oxylic acid anhydride
C8H10O3
Mol. Wt.: 154
40 40 2
45 45
3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
F2
Problem 8.42A
MASS
% of Base Peak 104
100
121
50 77 91 131
65 164
146
50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR 5
6
100 4 3
7 2
1
1720
9 OH
%Transmittance
8
50 10
2831 OCH3
1466
972
1350
1-methoxy-2-indanol
2939
748
3402
C10H12O2
1088
Mol. Wt.: 164
4000 3000 2000 1000

1
Wavenumber (cm-1)
H NMR 600 MHz
6 7 5 10
8
4400 4350 Hz 2750 2700 Hz 2000 1950 Hz 1650 1600 Hz
1 2 3 OH 3
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm
13
13
C/DEPT NMR
C/DEPT NMR 150.9
600 MHz
MHz
8 5
9 4 7 2
6 1 3
10
140 130 120 110 100 90 80 70 60 50 40 ppm

Problem 8.42B
ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm COSY 600 MHz
3
3.0 5 3.0 OH
6
4 3 3
3.5 2 3.5 10
7 1
9 OH
4.0 8 4.0
10
OCH3
2
4.5 1-methoxy-2-indanol 4.5
1
F1 C10H12O2
5.0 Mol. Wt.: 164 5.0
5.5 5.5
6.0 6.0
6.5 6.5
7.0 7.0
5 7
6
8
F2 HMQC 600 MHz
ppm
3
40 ppm 40
58
126
7 10
60 60
128
6
130
7.4 7.3 7.2 ppm 2
80 80
F1 1
100 100
120 120
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm
F2
Problem 8.42C
8 7 5 10 HMBC 600 MHz
6
1
2 3 3
OH
7.5 7.4 7.3 7.2 7.1 ppm 4.5 4.0 3.5 3.0 ppm
ppm ppm
40 40 3
5
50 50
6
4 3
7 2 10
9 1
F160 8
OH 60
10
OCH3
70 1-methoxy-2-indanol 70
C10H12O2
Mol. Wt.: 164
2
80 80
1
90 90
F1
ppm ppm
125 125 5
8
7
6
130 130
135 135
140 140 94
145 145
7.5 7.4 7.3 7.2 7.1 ppm 4.5 4.0 3.5 3.0 ppm
F2
Problem 8.43A
MASS
100 131
85 109
95 182 185
50 200
50 100 150 200

m/z
IR
100
90
%Transmittance
80
70
HO 10
1 O
3518
2978
1728
1458
1373
1188
1034
887
2 9
H3C 3 C
11 4 O4000
5
3000 2000 1000
1
Wavenumber (cm-1)
H NMR
6 600 MHz
7 8 10 11
Ethyl 3-hydroxy-3,6-
dimethylhept-6-enoate 8
C11H20O3
Mol. Wt.: 200
9 1260 1240 Hz 780 760 740 Hz
2 4
7
OH 5
4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

13
13
C/DEPT
C/DEPT NMR
NMR 150.9 MHz
600 MHz
7 9 2 4 5
3 8
10
1 6 11
170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.40A
ppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm COSY 600 MHz
11
10
1.5 1.5
4
8
2.0 2.0 5
2
2.5 2.5
F1
3.0 3.0
6
3.5 3.5 OH
4.0 4.0
9
4.5 4.5
7
F2 HMQC 600 MHz

ppm
10
20 20 8
11 5
40 40 4
2
60 60 9
3
HO 10
80 1 O 9 80
2 C
H3C 3
F1 100 11 4 O 100
5 7
6
120 7 8
120
140 dimethylhept-6-enoate 140 6
C11H20O3
Mol. Wt.: 200
160 160
1
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

F2
Problem 8.43C
HMBC 600 MHz
8 10 11
9
7 OH 2 5 4
ppm
10
20
8
11
30 5
40 4
2
50
9
60
70 3
F180
F1
HO 10
90 1 O 9
2 C
H3C 3
11 4
100 5
O
6 7
110 7 8
120 dimethylhept-6-enoate
C11H20O3
Mol. Wt.: 200
130
140
6
150
160
170 1
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

F2
Problem 8.44A
MASS
121
% of Base Peak 100
136
50
65 93
149 178
50 100 150
m/z
IR
100
%Transmittance
50
3325
2962
1658
1597
1281
1211
1173
841
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
9
3
7
2 8
6
OH
8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm 3.0 2.5 2.0 1.5 ppm
13
13
C/DEPT
C/DEPT NMR
NMR 150.9 MHz
600 MHz 6 8
O
5 7 9
1
2
3
4
2 OH
3 4'-Hydroxy valerphenone 8
C11H14O2 6 9
5 4 1 Mol. Wt.: 178 7
200 180 160 140 120 100 80 60 40 ppm

Problem 8.44B
ppm 8 7 6 5 4 3 2 1 ppm COSY 600 MHz
1 1 9
6 8 8
O 7
2 5
2
7 9
1
2 6
3 3
3
4
4 4
F1 OH
C11H14O2
Mol. Wt.: 178
6 6
OH
7 7 3
2
8 8
F2 HMQC 600 MHz

ppm
9
20 20 8
7
6
40 40
60 60
F1 80 80
100 100
3
120 120
8 7 6 5 4 3 2 1 ppm
F2
Problem 8.44C
HMBC 600 MHz
3
2 7 9
6 8
OH
8.0 7.5 7.0 ppm 3.0 2.5 2.0 1.5 1.0 ppm
ppm ppm
9
15 15
6 8
O
5 7 9
20 20
1
F1 2
8
25 3 25
4
OH 7
C11H14O2
Mol. Wt.: 178
35 35
6
ppm ppm 3
120 120
130 130 1
2
140 140
150 150
160 160 4
170 170
180 180
190 190
200 200 5
210 210
8.0 7.5 7.0 ppm 3.0 2.5 2.0 1.5 1.0 ppm
F2
Problem 8.45A
MASS
68
% of Base Peak 100
108
53
50
79 93 125 153
151 168
0
50 100 150
m/z
IR
100
%Transmittance
50
3078
2962
2893
2669
1705
1442
1412
1242
933
887
3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz 5,4
7 7 4 5
3
10
1
2900 2850 Hz 1600 1550 Hz 1200 1150 1100 1050 Hz

x64 9
OH
12 ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

13
13 9
C/DEPT
H2CNMR
C/DEPT NMR 150.9 MHz
600 MHz
H
3 4
1 2
7 6 5
8
CH3
HO 10
O
2-((1R,2S)-1-methyl-2-(prop-1-en-2-
yl)cyclobutyl)acetic acid 9 3 7 5 10 4
C10H16O2
Mol. Wt.: 168 1
8
6
2
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm
Problem 8.45B
ppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm COSY 600 MHz
10
1.5 1.5
1
54
2.0 2.0 5,4
7
2.5 2.5 7
3
F1 3.0 3.0
3.5 3.5
4.0 4.0
4.5 4.5
9
5.0 5.0
F2 HMQC 600 MHz

ppm
20 9 20 4
H2C H 1 10
3 4 5
40 1 2
40 7
7 6 5
8
CH3 3
HO
60 10 60
O
2-((1R,2S)-1-methyl-2-(prop-1-en-2-
yl)cyclobutyl)acetic acid
80 C10H16O2 ppm 80
Mol. Wt.: 168
100 20 100
1 9
F1
10
120 30 120
140 140
40
160 160
50
180 180
3.0 2.5 2.0 1.5 ppm
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

F2
Problem 8.45C
HMBC 600 MHz
9 1 10
7 5,4
3 7 4 5
ppm 5.0 4.8 ppm 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
4
20
1
25
9 10
H2C H
30 3 4 5
1 2
7 6 5
8
CH3
HO 35 10
F1 O
2-((1R,2 S)-1-methyl-2-(prop-1-en-2-
yl)cyclobutyl)acetic acid 7
C10H16O2
40
Mol. Wt.: 168
6
45
50
3
ppm 9
2
150
5.0 4.8 ppm 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
F2
105 Problem 8.46A
MASS
% of Base Peak
100
50 91
77 122 151
53 65 133 166
148
50 60 70 80 90 100 110 120 130 140 150 160

m/z
IR
100
787
%Transmittance
1365
50
1466
3332
1049
2916
4000 3000 2000 1000

1 Wavenumber (cm-1)
H NMR 600 MHz
10
4 5 1
9 9
2180 2160 Hz 1440 1420 1400 1380 1360 1340 1320 1300 1280 1260 1240 1220 Hz
8
7
3 4
11 OH
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
13
10 11
CH2CH2OH
2
1 3
7
8 6
9 4
9 4
5 11 5 10
3 Nopol 1
7 8
C11H18O
2 Mol. Wt.: 166 6
140 130 120 110 100 90 80 70 60 50 40 30 ppm

Problem 8.46B
ppm 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm COSY 600 MHz
8
1.0 1.0
4
1.5 1.5 7
2.0 2.0 5
10
2.5 2.5 4
9
F1 3.0 3.0
3.5 3.5 11
4.0 4.0
1 2
4.5 4.5
OH
5.0 5.0
3
5.5 5.5
F2 HMQC 600 MHz
ppm
20 10 11 20 8
CH2CH2OH
7
2
1 3 6
40 8 6
7 40
9 4 1
5
Nopol 11
60 60
C11H18O
ppm
Mol. Wt.: 166
F1
30 4
80 80
9
35
100 6 100
40
10
5
120 120 3
2.5 2.4 2.3 2.2 2.1 ppm
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
2
F2
OH
Problem 8.46C
INADEQUATE 150.9600
INADEQUATE MHzMHz
2 3 11 1
Hz
-15000 -15000
-10000 -10000
10 11
-5000 CH2CH2OH -5000
2
F1 0 1 3 0
7
8 6
9 4
5000 5000
5
Nopol
10000 10000
C11H18O
Mol. Wt.: 166
15000 15000
140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

10 F2 7 8
1 5 6 9 4
Hz
-16000 -16000
-14000 -14000
-12000 -12000
-10000 -10000
-8000 -8000
-6000 -6000
F1
-4000 -4000
-2000 -2000
0 0
2000 2000
4000 4000
45 40 35 30 25 20 ppm
F2
Problem 8.47A
MASS 105
% of Base Peak
100 277
100 FM (found) = 277.1083 by CI
77 136
50
154 50 305 317
50 100 150 200 250 300

m/z m/z
IR
100
2877
2939
%Transmittance
3456
50
717
1072
1751
1281
1712
4000 3000 2000 1000
1
Wavenumber (cm-1)
H NMR 600 MHz
3 6 9
2 12 10
7
4 10
OH
4800 4700 4600 4500 Hz 3300 3200 3100 3000 Hz 1500 1400 1300 Hz
O 11 8 12
O 13
O 9
12
10 8
CO 6 O
7
O
C O CH2OH O
5 2250 2200 Hz 1750 1700 Hz
1 11
2
HOH2C
4 3
5-(Benzoyloxy)hexahydro-4-
(hydroxymethyl)
C15H16O5
Mol. Wt.: 276
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
Problem 8.47B
ppm 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm COSY 600 MHZ
O 7
O 13
9
3 10
12 3
8
O 6
7
C O CH2OH 11
5
41 11 4
2
4 3
5 5
F1 5-(Benzoyloxy)hexahydro-4-
(hydroxymethyl)
9
C15H16O5 6
Mol. Wt.: 276
6 6
O
C O
7 O O 7
4 3
8 HOH2C 8 2
COSY 600 MHZ

ppm
7
10
2.5 2.5 10
12
12
3.0 3.0 8
3.5 3.5
11
F1
4.0 4.0
4.5 4.5
5.0 5.0 9
6
5.5 5.5
5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
F2
Problem 8.47C
13
2 3
1 8 1012
4 9 6 11 7
130 129 ppm 77.5 77.0 ppm

13 5
180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm
2 3
4 HMQC 600 MHz
6 9 11
7
ppm
O 12
O
40 O 13 8 10
9 C O
12
10 8 13
50 O O
O 6
7
OH 7
C O CH2OH
60 5
HOH2C
1 11 11
2 13
70
4 3
6
F1805-(Benzoyloxy)hexahydro-4-
(hydroxymethyl)
C15H16O5 12 8 12 10 9
Mol. Wt.: 276 10
90 ppm
100 35
12
110 10
40 8
120
3.0 2.9 2.8 2.7 2.6 2.5 2.4 ppm 3
130
2
4
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 ppm
F2
Problem 8.47D
2 HMBC 600 MHz

3 10
4 6 11 12 8
9 7 OH
8.2 8.0 7.8 7.6 7.4 ppm 5.0 4.5 4.0 3.5 3.0 2.5 ppm
ppm
12
10
40 O 8
O 13
9
12
50 10 8
O 6
7
7
C CH2OH
5 O
11
60 1
2 11
4 3
70 5-(Benzoyloxy)hexahydro-4-
(hydroxymethyl)
C15H16O5
Mol. Wt.: 276 6
80
9
F1
ppm
1 3
130 2
4
140
150
160
5
170
13
180
8.2 8.0 7.8 7.6 7.4 ppm 5.0 4.5 4.0 3.5 3.0 2.5 ppm
F2

ch08 Solutions

Hochgeladen von

Dokumentinformationen

Originaltitel

Copyright

Verfügbare Formate

Dieses Dokument teilen

Dokument teilen oder einbetten

Freigabeoptionen

Stufen Sie dieses Dokument als nützlich ein?

Sind diese Inhalte unangemessen?

Copyright:

Verfügbare Formate

ch08 Solutions

Hochgeladen von

Copyright:

Verfügbare Formate

CHAPTER 8 ASSIGNED PROBLEMS

200 180 160 140 120 100 80 60 40 ppm

50 60 70 80 90 100 110 120

4000 3000 2000 1000

2150 2140 Hz 1960 1950 Hz 1930 1920 Hz

4.0 3.5 3.0 2.5 2.0 1.5 ppm

50 100 150 100 m/z 150

40 50 60 70 80 90 100 110 120 130

2300 2280 Hz 2140 2120 Hz

1590 1580 1570 Hz

2260 2250 2240 2230 2220 2210 2200 Hz

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

50 60 70 80 90 100 110 120

7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 ppm

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

50 60 70 80 90 100 110 120 130

5 Methyl 5-bromo valerate 2

1 33.0 32.5 32.0 ppm

170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

50 60 70 80 90 100 110 120

3.5 3.0 2.5 2.0 1.5 1.0 ppm

50 60 70 80 90 100 110 120 130 140 150 160

50 60 70 80 90 100 110 120 130 140

7.4 7.3 7.2 7.1 ppm -80.1 -80.2 -80.3 ppm

50 60 70 80 90 100 110 120 130 140

1750 1740 Hz 640 Hz 570 560 Hz 300 290 Hz

200 180 160 140 120 100 80 60 40 ppm

50 60 70 80 90 100 110 120 130 140 150

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

50 60 70 80 90 100 110 120 130 140

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

50 60 70 80 90 100 110 120

3 2150 2100 Hz 1000 950 Hz 450 400 Hz

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

50 60 70 80 90 100 110 120

2720 2700 Hz 2600 2580 Hz 2440 2420 Hz 2200 2180 Hz

40 50 60 70 80 90 100 110 120

2060 Hz 2020 Hz 1820 Hz

180 160 140 120 100 80 60 40 ppm

50 100 150 150 m/z

3.5 3.0 2.5 2.0 1.5 1.0 ppm

200 180 160 140 120 100 80 60 40 ppm

50 60 70 80 90 100 110 120

100 150 200 250

50 100 150 150 200

2050 2040 Hz 1090 1080 Hz 615 610 605 Hz

140 130 120 110 100 90 80 70 60 50 ppm

50 60 70 80 90 100 110 120 130 140 150 160

6.85 6.80 6.75 6.70 6.65 ppm 6.00 5.95 ppm

4.0 3.5 3.0 2.5 2.0 1.5 ppm

170 160 150 140 130 120 110 100 90 80 70 60 50 40 ppm

50 m/z 100 130 140 150

1 6 F2 HMQC 600 MHz

3.5 3.0 2.5 2.0 1.5 ppm

50 60 70 80 90 100 110 120 130

1540 Hz 1140 Hz 500 480 Hz 440 Hz 3

5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm

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

4.0 3.5 3.0 2.5 2.0 1.5 ppm

170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 ppm

40 50 60 70 80 90 100 110 120 130

4 3680 3660 Hz 3300 3280 Hz 3220 3200 Hz 2760 2740 Hz

160 150 140 130 120 110 100 90 80 70 ppm