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CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 55 68
Problem 8.1
10041 112 84 97
50
40
50
60
70
IR100 %Transmittance
m/z O
80
90
100
110
1 2 3 4
502858 2927
Cycloheptanone C7H12O Mol. Wt.: 1121701 1342 1454 1161 856 941
400011
3000
2000 Wavenumber (cm-1)
1000
H NMR H NMR 300 MHz2 3
4
2.71313
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
C/DEPT C/DEPT NMR 75.5 MHz
2
4
3
1
200
180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.2124
10094
50
53
66
81
95
50
60
70
80
IR1004
m/zOH3
90
100
110
120
2 1 6 7
%Transmittance
50
5
OCH31493 1601 1284 687 768 837 945 1041 1149
m-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124
3398
2839 2947 3005
40001 1
3000
2000 Wavenumber (cm-1)
1000
H NMR H NMR 300 MHz5 6 4
2
7
2150
2140
Hz
1960
1950
Hz
1930
1920 Hz
OH
7.513 13
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
ppm
C/DEPT C/DEPT NMR 75.5 MHz
4 1 3 5
3 2
7
1 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS55 % of Base Peak
Problem 8.3M-1 83 39 41 M 53 65 66 84
100 50
40
45
50
55
IR100 %Transmittance
m/z
60
65
70
75
80
85
503332 2877 2939 2978 2229 2291 1454 1138 1227 1319 1014 741
40001 1
3000
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz H NMR
5 11280 1260 Hz 680 660 Hz
4 OH
4.013 13C/DEPT
3.5
3.0
2.5
2.0
1.5
ppm
C/DEPT NMR 75.5 MHz
HO H 2C1
4
C2
C3
CH25 CH3
3
CDCl3
2-Pentyn-ol C5 H 8 O Mol. Wt.: 84
5 4
1 278.0 77.5 77.0 76.5 ppm
95
90
85
80
75
70
65
60
55
50
45
40
35
30
25
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS75 % of Base Peak
Problem 8.4CI Reagent gas methane110 49 61 77 99 97 112 M 114 148 146 111 x 30 113 146 75 77 115 148 150 152
100 50
100 50
50
IR100 %Transmittance 90 80 70
m/z
100
150Cl Cl 1 CH 3 Cl CH2 2 CH2 1,2,3-Trichloropropane C3H5Cl3 Mol. Wt.: 1462962 3016
100
m/z
150
1435
1219 1288
910
663 717
40001 1H
3000
H NMR 300 MHz NMR
2000 Wavenumber (cm-1)
1000
1+3
2
4.3513 13C/DEPT
4.30
4.25
4.20
4.15
4.10
4.05
4.00
3.95
3.90
3.85
3.80
ppm
C/DEPT NMR 75.5 MHz
1+3 2
75
70
65
60
55
50
45
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.5m/z 126 (M) 127 (M+1) 128 (M+2) %M 100.0 8.2 4.9
111
100 5039 43 49 57 83
126
40
50
60
70
IR100 %Transmittance
80 m/z
90
100
110
120
130
50
3089
1662
1415
1273
856 933 1061
725
590
40001 1
3000
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz H NMR3 1 2 6
2300
2280 Hz
2140
2120 Hz
4
5ppm
7.513 13 C/DEPT
7.0
6.5
6.0
5.5
5.0
4.52 1
4.0
3.5
3.0
2.5
C/DEPT NMR 75.5 MHz
3
S
4
O5 6 CH3
1
3
2
Ethanone, 1-(2-thienyl)2-Acetylthiophene C6H6OS Mol. Wt.: 126
6
5
4
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 105
Problem 8.6x 10 186 184 51 77
100 50
IR100 90 %Transmittance 80 70
50
100
m/z
150
2985 3032
1450 1496
1211
964
594 694 764
40001
3000
H NMR 300 MHz3
2000 Wavenumber (cm-1)
1000
2
41590 Hz 640 630 620 Hz 1580 1570 Hz
6
2260
2250
2240
2230
2220
2210
2200
5
7.513
7.0
6.5
6.0
5.5
5.0H3C6
4.5Br
4.0
3.5
3.0
2.5
ppm
C/DEPT NMR 75.5 MHz
5 1
2 3 4
4 3 1140 130 120 110 100
2
(1-Bromoethyl)benzene C8H9Br Mol. Wt.: 184
5
6
90
80
70
60
50
40
30 ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.7109 124 81 53 63 75
100 50
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
50
3348
2835 2951
1859
1512 1612 1701
1234
1034
733 825
513
40001 1
3000
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz H NMR2 3 5
OH
7.013 13
6.5
6.0
5.5
5.0OH4 3 2 1
4.5
4.0
3.5
ppm
C/DEPT NMR 75.5 MHz C/DEPT
OCH35
3 1 4
2
p-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124
5
150
140
130
120
110
100
90
80
70
60
50
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.8128
10064 130 92 73
50
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
130
50
3464 3521
3039 3074
1200 1338 1454 1481 1585
1030
679 748
40001 1 H
3000
H NMR 300 MHz NMR3 6 5 4
2000 Wavenumber (cm-1) OH1 6 5 4 2 3
1000
Cl
OH
o-Chlorophenol C6H5ClO Mol. Wt.: 128
7.413 13
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
5.4
ppm
C/DEPT NMR 75.5 MHz C/DEPT
5 3
4
6
1
2
155
150
145
140
135
130
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 55 87 73
Problem 8.9x 20 115 196 194 135 137 163 165
100 50 0 50 100 %Transmittance
100
IR
m/z
150
50
2954
1736
1365 1435
1203
748
40001 1 H
3000
H NMR 300 MHz NMR6Br5 4
2000 Wavenumber (cm-1)O6 3 2 1
1000
O
5
Methyl 5-bromo valerate C6H11BrO2 Mol. Wt.: 194
2 4 3
3.613 13
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
ppm
C/DEPT NMR 75.5 MHz C/DEPT
5 2
4 6
3
1
33.0
32.5
32.0
ppm
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS54 % of Base Peak
Problem 8.1067 84 93 111 126
100 50
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
3344
2873 2931 2958
1466
1331
1045
849
40001 1 H
8
30007 6
H NMR 300 MHz NMR
2000 4 5 1 OH Wavenumber (cm-1) 23
1000
3-Octyn-1-ol C8H14O Mol. Wt.: 126
8 6 7
1
2
5
OH
3.513 13 C/DEPT
3.0
2.5
2.0
1.5
1.0
ppm
C/DEPT NMR 75.5 MHz
1
6 2 7
5
8
84
82
80
78
ppm
485 80 75
370 65 60 55 50 45 40 35 30 25 20 ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.11162 164 98 73 126 128
10063
50
50
60
70
80
90
IR100 %Transmittance
100 110 m/z
120
130
140
150
160
503521 3097 1188 1277 1404 1477 1585 725 814 555
40001 1 H
3000
H NMR 300 MHz NMR3 6 5
2000 Wavenumber (cm-1)OH1 6 5 4 2 3
1000
Cl
OH
7.413 13 C/DEPT
7.2
7.0
6.8
6.6
Cl 2,4-Dichlorophenol C6H4Cl2O Mol. Wt.: 162 6.4 6.2 6.0
5.8
5.6
5.4
5.2 ppm
C/DEPT NMR 75.5 MHz
3 1
5
6
4
2
155
150
145
140
135
130
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.12
MASS% of Base Peak
123 95 75 50 63 138
100 50
IR100 %Transmittance
50
60
70
80
90 m/z
100
110
120
130
140
50
3356
3005 3074
1597 1685
1157 1265 1358
841 960
567
40001
3000
2000 Wavenumber (cm-1)1
100019
H NMR 300 MHz2 3 6
F NMR 282.4 MHz
H Coupled
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 3.013
ppm5 1
-104.4COCH32 3 4 6
-104.5 ppm
C/DEPT NMR 75.5 MHz
2
3
F 4-Fluoroacetophenone C8H7FO Mol. Wt.: 138130 128 126 124 122 120 118 ppm
6
5
4 1
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.1396
100 5050
70
75 77
50
55
60
65
IR100 %Transmittance
70 m/zF1 2 3
75
80
85
90
95
953749 3062
4
Fluorobenzene C 6H 5 F Mol. Wt.: 96
1504 1604 1697
1234
756
40001 1H
3000
2000 Wavenumber (cm-1)19
1000
NMR H NMR 300 MHz
F NMR 282.4 MHz1
H Coupled
3
2 4
7.413 13
7.3
7.2
7.1
ppm
-80.1
-80.2
-80.3 ppm
C/DEPT NMR 75.5 MHz C/DEPT
3 4130 128 126 124 122 120 118 116 ppm
2
1165 160 155 150 145 140 135 130 125 120 115 ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS82 % of Base Peak
Problem 8.14
100 50138 67 95 123
54
50
60
70
80
IR100 %Transmittance
90 m/z
100
110
120
130
140
502870 2958 1670 1381 1246 903 525
40001 1 H
3000
H NMR 300 MHz NMR
2000 Wavenumber (cm-1)
1000
6 4
7
89
1750
1740 Hz
640
Hz
570
560 Hz
300
290
Hz
2ppm
6.013 13
5.5
5.0
4.5
4.0
3.5
3.0
2.57
2.0
1.5
C/DEPT NMR 75.5 MHz C/DEPT4 9
CH33 2 5 6 1
H 3C H3 C8
O
89 6 4 5
2 1200 180
Isophorone C9H14O Mol. Wt.: 138
7
3160 140 120 100 80 60 40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS54 % of Base Peak
Problem 8.15
50
68 81 79 93 95 107 109 119 121
149 147
50
60
70
80
90
IR100 %Transmittance 90 80 702970
m/z
100
110
120
130
140
150
2245
1435
1250
756
40001 1
3000
H NMR 300 MHz H NMR4Br4 3
2000 Wavenumber (cm-1) 22 1
1000
N 4-Bromobutanoyl nitrile C4H6BrN Mol. Wt.: 147
3
3.613 13
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
C/DEPT NMR 75.5 MHz C/DEPT
3 4 1120 110 100 90 80 70 60 50 40 30 20
2
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS106 % of Base Peak
Problem 8.16
100 5077 137
50
60
70
80
IR100 %Transmittance 90 803348 3194 2931
m/z
90
100
110
120
130
140
1442 1512 1620
1049
825
40001 1H
3000
H NMR 300 MHz NMR3 25 4
2000 Wavenumber (cm-1)
1000
6 OH3 2 ppm
5
7.513 13
7.0
6.5
6.0
5.5
5.0
4.5OH
4.0
3.5
3.0
2.5
2.0
1.5 ppm
C/DEPT NMR 75.5 MHz C/DEPT
6
5 1 2 3
OH
2
3
4
NH2 p-Aminophenylethanol C8H11NO Mol. Wt.: 137
6
5
4140
1130 120 110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.17119
100 50
64 76
91
50
60
70
IR100 %Transmittance 90 80 703309
80 m/z
90
100
110
120
2245
1481 1589
1342
671 787
40001 1H
3000
H NMR 300 MHz NMR2
2000 Wavenumber (cm-1)
1000
3
OH
7.613 13
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
C/DEPT NMR 75.5 MHz C/DEPT2 5 3 4 1
N
C
OH
p-Cyanophenol C7H5NO Mol. Wt.: 119
2
3
4
5
1115 110 ppm
165
160
155
150
145
140
135
130
125
120
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.18163
100 5077 91 135 178
50
100
IR100 %Transmittance
m/z
150
50
3572
2870 2962
1458
1149 1203
748
40001 1
3000
2000 Wavenumber (cm-1)
10006
H NMR 300 MHz H NMR
3
2150
2100 Hz
1000
950 Hz
450
400
Hz
4
OH
51.5 ppm
7.013 13C/DEPT
6.5
6.0
5.5
5.0
4.5
4.0
3.56 2 3 4 5
3.0
2.5
2.0
C/DEPT NMR 75.5 MHz
OH1
6
3 4 1150 140
2,6-Diisopropyl phenol C12H18O Mol. Wt.: 178
6 5
2130 120 110 100 90 80 70 60 50 40 30 20 ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.19106 78 121
100 5051
50
60
70
IR100 %Transmittance
80 m/z
90
100
110
120
50
3363
3047
1689
1419
1273
957
702
40001 1H
3000
H NMR 300 MHz NMR5
2
2000 Wavenumber (cm-1) 3
1000
4 7
2720
2700 Hz
2600
2580 Hz
2440
2420 Hz
2200
2180 Hz
9.013 13C/DEPT
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.03 4 5
4.5
4.0
3.5
3.0
ppm
C/DEPT NMR 75.5 MHz
2 1 7 6
N
C O
CH3
5 6
4
3 1
2
2-Acetylpyridine C7H7NO Mol. Wt.: 121
7
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.20108 123
100 5053 80
40
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
50
3109
2947
1651
1404
1095
633 741
40001 1H
3000
H NMR 300 MHz NMR
2000 Wavenumber (cm-1)
1000
5
7
4
2060 3
Hz
2020
Hz 1820
Hz
2
7.013 13
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
ppm
C/DEPT NMR 75.5 MHz C/DEPT3 4 2 1 7 6
N
CH3
4 1 6180 160 140
2
3
H3C5
O
1-Methyl-2-acetylpyrrole C7H9NO Mol. Wt.: 123
5
7
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 43 x 20 85 159
Problem 8.21CI Reagent gas methane 100103 158
100 5057
50 50 100 150 150 m/z
187
IR100 %Transmittance
m/z
502962 1651 1720 1319 1034 1149
40001 1
3000
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz H NMR7 1 3 5 6
3.513 13C/DEPT
3.0
2.5
2.0
1.5
1.0
ppm
C/DEPT NMR 75.5 MHz7 1 2 3 4
O
5
6 7
O O Isobutylacetoacetate C8H14O3 Mol. Wt.: 158
5
3 1
6
7
2
4
200
180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.22119
100 50
64 76
91
50
60
70
80
IR100 90 %Transmittance 80 703309
m/z
90
100
110
120
2245
1481 1589
1342
671 787
40001 1
3000
H NMR 600 MHz 30042 5 64 5
2000 Wavenumber (cm-1) OH3 2 1 6 7
1000
C
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 75.5 MHz C/DEPT NMR 600 MHz
5 3
6
4
2
7155 150 145 140 135 130 125 120 115
1
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 183 185 200 198
Problem 8.23x 20
100 5075 155 157
224
226
264 262 260
100
IR100 %Transmittance
150 m/z
200
250
50
3356
2962 3059 3089
1396 1485 1585 1685
1223
995 1068
810
617
40001 1H
3000
H NMR 300 MHz NMR2 3
2000 Wavenumber (cm-1)6 8 5
1000
7
7.9
7.8
7.7
7.6
ppm
3.6
3.4
3.25 1 2 3 4 6
3.07 8
2.8
2.6
2.4
ppm
13 13C/DEPT
C/DEPT NMR 75.5 MHz
COCH2CH2CH2Cl
3 5 1
2
Br 4Bromo-4-chlorobutyrophenone C10H10BrClO Mol. Wt.: 260
6
7
8
4
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.24
MASS% of Base Peak
100 55 69 74 83 147
100 50
CI Reagent gas methane
128
50175 187
50 m/z
100
150
150
m/z
200
IR100 %Transmittance
50
2978 3039
2669
1709
1238 1277 1419 1466
930
40001 1H
3000
H NMR 300 MHz NMR2x OHx64
2000 Wavenumber (cm-1)
1000
4 3 2
6
1213 13C/DEPT
11
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2 ppm
C/DEPT NMR 75.5 MHzO HO 12
CH2 C 5 CH CH2 OH CH36 4
3
O
15
2-Methyl glutaric Acid C6H10O4 Mol. Wt.: 146
2
4 3
6
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.25
MASS% of Base Peak
91
92
CI Reagent gas methane 100 5093
100 5066 51
50
60
IR100 %Transmittance 90 80
m/z
70
80
90
80
m/z
90
2962 3055
1720
1342
1065
725 802
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz1
2
3
2050
2040
Hz
1090
1080 Hz
615 610 605
Hz
7.013
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
C/DEPT NMR 75.5 MHz
3
2
1
1
Bicyclo[2,2,1] hepta-2-5-diene C7 H 8 Mol. Wt.: 92
2
3
140
130
120
110
100
90
80
70
60
50
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.26
M 156 M+2
10063
5098 121
158
50
60
70
80
90
IR100
100 110 m/z
120
130
140
150
160
586
%Transmittance
2900
50
933 1041
802
1234
1473
40001
3000
H NMR 600 MHz6 4
2000 Wavenumber (cm-1)
1000
3
7
6.8513 13
6.803 4 5
6.75
6.70
6.65
ppm
6.00 5.95
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz2
O7
Cl
1 6
O
5-chloro-1,3-benzodioxole C7H5ClO2 Mol. Wt.: 156
4
36
7
1155 150
2145 140 135 130
5
125
120
115
110
105 ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 42 55
Problem 8.27A
100 5084 70 114
40
50
60
70
IR100 %Transmittance
m/z
80
90
100
110
50
2931
1728
1442
1057 1165
856
571
400011
3000O2 1
2000 Wavenumber (cm-1)
1000
H NMR 300 MHz H NMR63 4
1O6 5
2 3 5
4
-Caprolactone C6H10O2 Mol. Wt.: 114
4.013 13 C/DEPT
3.5
3.0
2.5
2.0
1.5
ppm
C/DEPT NMR 75.5 MHz
6 1
43 2 5
170
160
150
140
130
120
110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.27B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
COSY 300 MHz
1.5 2.02
1.5O1
41 2 3 4 5 6
2.0O6
5 3
2.5
3 4 5
2.5 3.0 3.5 4.0
2
F13.0 3.5 4.0
-Caprolactone C6H10O2 Mol. Wt.: 114
6
F2ppm6 2 5 4 3
HETCOR 75.5 MHz HETCO 300 MHz
1.5 2.0 2.5
1.5 2.0 2.5 3.0 3.5 4.0 4.5 ppm
F13.0 3.5 4.0 4.5 65 60 55 50 45 40 35 30 25
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 55 x 10 82 90 92 120 118
Problem 8.28ACI Reagent gas methane
100 50 50
69
137
5
139
IR100 %Transmittance
m/z
100
130
m/z
140
150
50
3332
2862 2939
1458
1057
648 725
40001
3000
H NMR 600 MHz1 6
2000 Wavenumber (cm-1)
1000
HO 1
2
3
4
5 6
Cl
1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136
5
2
4 3
OH
3.613 13 C/DEPT
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
1.4 ppm
C/DEPTNMR 600 MHz NMR 150.9 MHz
1
6
5
2
4
3
60
55
50
45
40
35
30
25
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.28B
ppm
3.5
3.0
2.5
2.0
1.5
ppm
COSY 600 MHz
1.5
1.5
2.0HO 12 3 4 5 6
2.0Cl
F1
2.5
1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136
2.5
3.0
3.0
3.5
3.5
1
6
ppm
OH
F2
5
2 4 3
HMQC 600 MHz
25 30 35 405 2 OH
254
3
30 35 40 45 50 55 33 2.0 1.8 2.5 1.6 1.4 2.0 ppm 1.5 601 6
F145 50 55 60
ppm 32
3.5
3.0
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS95 % of Base Peak
Problem 8.29A
100 5045 67 55 69 81 110 113 128
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
130
503344 2924 2966 1377 1450 1041 1126 825
400011
3000
2000 Wavenumber (cm-1)
1000
H NMR H NMR 300 MHz7 8
1
1540
Hz
1140
Hz
500
480 Hz
440
Hz
3 4 OH
5
2
5.013 13 C/DEPT
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
C/DEPT NMR 75.5 MHz
7 5 8 6 4 3
OH2 1
5 6
6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128
2
3 8
4
1 7
130
120
110
100
90
80
70
60
50
40
30
20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.29B
ppm 5.5 1.0 1.5 2.0 2.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0 ppm 1.0
COSY 300 MHz1
1.5 2.0 2.5 3.0 3.5
3 OH 4
7 8
F1 3.03.5 4.0 4.5 5.084 1 7
2
4.0 4.5 5.05
5
F2 2
3
HETCOR 75.5 MHz HETCO 300 MHz
ppm 1.07
1.55
OH4 3 2 1
2.0 2.5
8
6
6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128
F1
3.0 3.5 4.0 4.5 5.0 5.5 120 100 80 60 40 20 ppmOH
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS88 % of Base Peak 223 225
Problem 8.30ACI Reagent gas methane 100251 253 143 159 177 179 50 194 263 265
10069
50 0
50 100
100
m/z
150
230
IR
240 250 m/z
260
%Transmittance
502870 2939 1736 1458 1188 1034
400011 H
3000
H NMR 300 MHz NMR 600 MHz
2000 Wavenumber (cm-1)
1000
8
7
6
2
5
3
4
4.013 13 C/DEPT
3.5
3.0
2.5
2.0
1.5
ppm
NMR 600 MHz C/DEPT NMR 75.5 MHz
Br
6
5
4
3
2
1
O
7
8
2,6,5 7
4 3 8
O
1
Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.30B
ppm 1.0
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm 1.0
COSY 300 MHz8 4 3 5 2
1.5
1.5
2.0
2.0
F1
2.51 1
2.5
3.0
3.06
3.5
3.57
4.07
4.0
F2 2 6 5 4 3
8
HETCOR 75.5 MHz HETCO 300 MHz1.0
ppm 1.0Br6 5 3 1
4
2
O
7
8
8 4 3 5 2
O 1.5 Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222 2.0
1.5
2.0
F1 2.53.0
2.5
3.06
3.5
3.57
4.0 60 55 50 45 40 35 30 25 20 15
4.0 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.31A134
10041 94
50
65
77
91 105
119
40
50
60
70
80
IR100 %Transmittance
m/z
90
100
110
120
130
502866 2916 3032 3066 1496 1601 1242 690 752
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz3 4 2 5
3680
3660
Hz 3300
3280
Hz 3220
3200
Hz
2760
2740
Hz
6
7
7.413 13
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
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz5 1 2 6 7
OCH2CH=CH2
3 4 1 6 7
24
3
Allylphenyl ether C9H10O Mol. Wt.: 134
5
160
150
140
130
120
110
100
90
80
70
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.31B
ppm 7.5 4.5
7.0
6.5
6.0
5.5
5.0
4.5
ppm 4.5
COSY 600 MHz
5.0
5.0
5.5
5.5
F16.0 6.0
6.5
6.5
7.0
7.0
3
4
2 65 6 7
F2
ppm 70 80 90 1004
7
5
HMQC 600 MHz
OCH2CH=CH21 2 3
70 80 90 100diastereotopic
5
Allylphenyl ether C9H10O Mol. Wt.: 134
F1 110120 130 140 150
1102
120 1306
7
4 3
140 1501
7.5
7.0
6.5
6.0
5.5
5.0
4.5
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.32A
MASS% of Base Peak 95 x 20
100 5055 67 110 109 121 139 136 154
50
60
70
80
90
IR100 %Transmittance
100 m/z
110
120
130
140
150
50
3317
2877 2951
1712
1365
1227
1057
829
40001
3000
H NMR 600 MHz
2000 Wavenumber (cm-1) 3
1000
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
4.013 13
3.5
3.0
2.5
2.0
1.5
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz10 9
H 3C6 5 4
CH37 1
8 2
CH3
3 OH
2
Borneol C10H18O Mol. Wt.: 154
4
3
5
6
9 10
8
1 7
75
70
65
60
55
50
45
40
35
30
25
20
15 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.32B
ppm
4.0
3.5
3.0
2.5
7 2.0
1.5
1.0
ppm
COSY 600 MHz9.10,8 3 5 6
1.0 1.5 2.0
1.0 1.5 2.010 9
OH 5 6 3
4
F12.5 3.05
H 3C6 4
CH37 1
2.5 3.0 3.5 4.02
8 2
CH3
3 OH
3.5 4.0
Borneol C10H18O Mol. Wt.: 154
F2ppm ppm 20 15 30 20 40 25 0.90diastereotopic
HMQC 600 MHz8
20 30 40 50 60 702 7 1
10 9 6 5
3 4
F150 60 70
0.85
ppm
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS85 % of Base Peak
Problem 8.33A
100 50
57
70
114
50
60
70
IR100
m/z
80
90
100
110
656
2885 2970
1358 1466
%Transmittance
972
50
1180
1774
40001
3000
H NMR 600 MHz6 5 3 4 2 1
2000 Wavenumber (cm-1)
1000
6
4
O
O
2 3 3 5 5
-Caprolactone C6H10O2 Mol. Wt.: 114
4.013 13
3.5
3.0
2.5
2.0
1.5
1.0
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
2 4
5
3 6
1
29
28
ppm
180
160
140
120
100
80
60
40
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.33B
ppm 4.5 1.0 1.5 2.0
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm 1.0 1.53
COSY 600 MHz6
5
2.03
F1 2.56
2.53 4 5 2 1
2
3.0 3.5 4.0
O
O
3.0 3.5 4.04
-Caprolactone C6H10O2 Mol. Wt.: 114
F2ppm 10 20 30diastereotopic
HMQC 600 MHz6
10 20 30ppm
40
403 5 22.5 2.0 1.5 ppm
F1 5060 70 80
28
50 60 70 804
30
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS41 % of Base Peak
Problem 8.34A69 55 81 95 109 123 138 156
100 50
40
50
60
70
80
90
IR100 %Transmittance
m/z
100
110
120
130
140
150
160
503332 2924 1381 1450 1057 833
40001
3000HO1
H NMR 600 MHz
2000 9 10 Wavenumber (cm-1) CH3 CH36 2 3 4 5 7
1000
9
8 10
CH38
Citronellol C10H20O Mol. Wt.: 156
6
1
5 OH3.5 3.0 2.5 2.0
3
2
4
5.013 13
4.5
4.0
1.5
1.0
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
6 7
9
5 1 24 3
8
1026 25 ppm
130
120
110
100
90
80
70
60
50
40
30
20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.34B
ppm 5.5 1.0 1.5 2.0 2.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
COSY 600 MHz10 4 2 OH 5 3 8 9
1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0
F1
3.0 3.5 4.0 4.5 5.0
1
6
F2ppmHO1 2 10 9 6
HMQC 600 MHz10
20 CH33
CH37
20
8 95 3 4 2
40 4 5 Citronellol C10H20O Mol. Wt.: 156 60
CH38
40
60 ppm
1
F1 8020 100 30 40 2.0 1.5 1.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm 1.0
80
100
120
1207
6
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS95 % of Base Peak
Problem 8.35A81 41 55 69 108 152 137
100 50
50
60
70
80
IR100 %Transmittance
90 100 m/z9
110
120
130
140
150
H3C 7 CH35 6 1 10CH3 4 3
8
1273
748
1450
2
1041
502954
O1743
Camphor C10H16O Mol. W 152 t.:
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz
8 9
10
3
4 52.2 2.1 2.0 1.9
3 61.8 1.7 1.6 1.5
61.4
5
2.413 13
2.3
1.3
1.2
1.1
1.0
0.9
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
4 3 2 1 7
6
5
9
8
10
220
ppm
55
50
45
40
35
30
25
20
15
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35B
ppm 0.6 0.8 1.0 1.2
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm 0.6 0.8 1.0 1.2 1.4 1.6
COSY 600 MHz
10 9 8 5 6 6
F1
1.4 1.6 1.8 2.0 2.2 2.4
1.8 2.0 2.2 2.43 5 4
3
F2ppm 10 10
HMQC 600 MHz
10
20
20
8 9 5 6
30
9
F140
H3C 7 CH35 6 1 10CH3 4 3 2
8
30
40O
4 3 7
50
Camphor C10H16O Mol. W 152 t.:
501
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35C
INADEQUATE 150.9 MHz INADAQUATE 150.9 MHz2Hz9 8
1
3
-20000 -15000 -10000 -5000
H3C 7 CH35 6 1 10CH3 4 3 2
-20000 -15000 -10000
O
F1 05000 10000 220 Hz
Camphor C10H16O Mol. W 152 t.:
-5000 0 5000 10000 ppm
200
180
160
140
120
F2
100
80
60
40
20
1-25000 -24000 -23000 -22000
7 43
6
5
9 8
10-25000 -24000 -23000 -22000 -21000 -20000 -19000 -18000 -17000 ppm
F1-21000 -20000 -19000 -18000 -17000 65 60 55 50 45 40 35
F2
30
25
20
15
10
5
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 43
Problem 8.36Ax 30 70 55 115 130
100 50 40 50
60
70
80
IR100
m/z
90
100
110
120
130
1373 1466
%Transmittance
2877 2962
1041
50 4000 3000 2000 Wavenumber (cm-1) 1
1242
1743
1
1000 7 is doublet
H NMR 600 MHz
6 is triplet
2350 Hz
2300 Hz
1000 Hz
850
Hz
700
Hz
550
Hz
3
In the above insets each tick mark is 10 Hz 4 51.5
5ppm
3.513 13
3.0
2.5
2.0
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
O3
H3C 2 O1
4
5
6
CH3
7 CH3
3 5 4 1 7 6
2
2-Methylbuty acetate C7H14O2 Mol. Wt.: 13090 80 70 60 50 40
170 160 150 140 130 120 110 100
30
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.36B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
COSY 600 MHz6
1.0 1.5 2.0
1.0 1.5 2.0 2.5 3.0 3.53 5 5 4 1 7
F12.5 3.0 3.5 4.0
4.0
F2ppm 10ppm 10
HMQC 600 MHz
106
6 7 1 5
20 30 4015
20 30
70.95 0.90 0.85 ppm
4
40 504 5 6
F150 60 701
O3
H3C 2 O
CH3
7 CH3
60 703
2-Methylbuty acetate C7H14O2 Mol. Wt.: 130
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS111 % of Base Peak
Problem 8.37Am/z 151 (M-1) 152 (M) 153 (M+1) 154 (M+2) %M 37.5 100.0 12.7 5.2
100 5069 83
152
50
60
70
80
90
IR1003008 3093
m/z
100
110
120
130
140
150
%Transmittance
1057
501419 1234 1651
957
725
40001
3000
2000 Wavenumber (cm-1)
1000
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
7.513 13
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
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHzO S1 2 3 4
C5
6 8
7
1 5180 160
3
2
cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152
7 8 6
4140 120 100 80 60 40 20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.37B
ppm 1 2 3 4 5 6 7 8
8
7
6
5
4
3
2
1
ppm 1 2
COSY 600 MHz87
6
3 4 5 6 7 82 1 3
F1
F2ppm
HMQC 600 MHz
20S4 3
O C5 6 8 1 2 7
20
6
78
40
40
60
F180
cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152
60
80
100
100
120
1202 3 1
8
7
6
5
4
3
2
1
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS% of Base Peak 121
MASS100103 77 91
Problem 8.38A164 136
60
70
80
90
100
m/z
110
120
130
140
150
149
65
50
160
IR%Transmittance
1002870 663 764
949
3201
2962
1265 1412 1473 1550 1612
50
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz3 6
7
5
8
9 10
3940
3920
Hz
3880
3860 Hz
3720
Hz
1280
Hz
320
300
Hz
OH
913
8
7
6
5
4
3
2
1
ppm
C/DEPT NMR 150.9 MHz7 6 5 1
O2 3 4
OH
2
1 6 537
H 3C 810
CH39
9 8
10
171.5
171.0 ppm
4
-Thujaplicin C10H12O2 Mol. Wt.: 164
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.38B
ppm
7
6
5
4
3
2
1
ppm
COSY 600 MHz9 10O
1 2 3
ppm 6.8
6.6
6.4
6.2
ppm
15 7
6.2 6.4 6.6
2 3
86
7
1 2 3 4
OH
F14 5 6 7
36
5
4 5 6 7
H 3C 810
CH39
-Thujaplicin C10H12O2 Mol. Wt.: 164
F2ppm 20 40 60ppm
HMQC 600 MHz
209 10
407 3 5
8
125 130
60 80
F1 80100 120 140 7
135
6140 6.8 6.6 6.4 6.2 ppm
100 120 140
7 3 5 6
6
5
4
3
2
1
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.38C
INADEQUATE 600 MHz INADEQUATE 150.9 MHz4Hz -20000 -15000 -10000 -5000 -20000 -15000 -10000 -5000 0 5000 10000 15000 20000 160 2 1 Hz 0 0 140 120 4 100 80 60 40 3 7 20 ppm
8
9 10
F1
0
5000 10000 15000 20000
F2
6
5
5000
5000
F110000 10000
150007 6 1
O2 3 4
15000
OH20000
200005
175
170
165
160
155
H C 8 CH3 150 3 10 145 140 135 9
F2 -Thujaplicin
130
125
120
115
ppm
C10H12O2 Mol. Wt.: 164
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.39A123 83 55 151 69 95 110 232 230
100 5041
50
100
m/z
150
200
IR100 %Transmittance 90 802954 1219 1365 1442 1473 1034
70
1751
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz8
10 9
2800
Hz
1350
1300
1250
1200
1150
1100
1050
1000
950
900
850
Hz
3
4
5
5
6
6
4.513
4.0
3.5
3.09 8 7
2.5
2.0
1.5
ppm
C/DEPT NMR 150.9 MHz
H3 C5 6
CH34 3
1 10
2
Br
8
9
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230
3
4
6
5
10
2
20.0
19.9
19.8
ppm
1
7ppm
200
180
160
140
120
100
80
60
40
20
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39Bppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
COSY 600 MHz
1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5
1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5
9 8 6 6 5 5 4
10
F1
3
F2ppm 109 8 7
HMQC 600 MHz
H3 C5 6
CH34 3
10
10
20
1 10
2
20Br
89 5 6
30
F140
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230
30
40
750 50
4 3 1
60 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
60 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39C
INADEQUATE 150.9 MHz INADEQUATE 600 MHz2Hz
13
-20000 -15000 -10000
-20000 -15000 -10000 -5000 0 5000
F1-5000 0 5000
200
1Hz
180 3
160 4
140
120
7
F2
100 6
80
60
40
5
20 10
ppm
-25000 -24000 -23000 -22000
-25000 -24000 -23000 -220009 8 7
F1-21000 -20000
H3 C5 6
CH34 3
-21000 -20000 -19000 -18000 -17000 ppm
1 10
2
Br
-19000 -18000 -17000 60 55 50 45 40 35
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230
F2
30
25
20
15
10
5
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
Problem 8.40A108 81 71 93 111 139 55 136FM (found) = 154.1351 154
100
50
50
60
70
80
90
IR100
m/z
100
110
120
130
140
150
841
%Transmittance
1373 1466
1080
1219
502970
987
40001
3000
H NMR 600 MHz
2000 Wavenumber (cm-1)
1000
8,9 4,6 3,7
10
3,7
4,6 2
2.113 13
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.1
1.0 ppm
C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz6 7 4 3 2 5 1 10
CH3 O CH38
9 CH3
4,6 2
8,9 10
3,7 7
1
5
Cineole C10H18O M Wt.: 154 ol.
75
70
65
60
55
50
45
40
35
30
25
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.40B
ppm 2.2 1.0
2.0
1.8
1.6
1.4
1.2
1.0
ppm 1.0
COSY 600 MHz10
1.2
1.22
8,9
1.4
1.4
3,7 4,6
4,6
F11.6 1.6
1.8
1.83,7
2.01 4 5 6
2.0
F2ppm
HMQC 600 MHz
22 246 7 10
223,7
24 26
CH31 O 2
264
5 3
CH38
F1 2830 32 34 2.2 2.0
10
9 CH3
28 30
Cineole C10H18O M Wt.: 154 ol.
8,9
4,6
322
34 1.8 1.6 1.4 1.2 1.0 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.41A
MASS82 % of Base Peak
10054
67
CI Reagent gas methane155
100110
FM (found) = 155.0711 by CI
50 50 160183 195
50
IR100
m/z
100
170 180 m/z
190
1450
%Transmittance
2862 2947
50
1859 1790
1219
903
40001
30003 4
H NMR 600 MHz2
2000 Wavenumber (cm-1) O2 1
1000
4
O O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. W 154 t.:
3
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 1.413 13
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
2 3 1 4
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS 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
F12.5 2.5
3.0
3.0
2
F2ppm
HMQC 600 MHz
4 3
25O2 1
25
3
30
4
30O
F135O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. W 154 t.:
35
40
40
2
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
45 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42A
MASS104 % of Base Peak
100121
5065
77
91
131 164 146
50
60
70
80
906
IR100 %Transmittance7
100 110 m/z5 4 9 8 1 3 2
120
130
140
150
160
1720
OH
502831 2939 3402
OCH31350 1466 972
10
1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
748
1088
40001
3000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz8 6 7 5
10
4400
4350
Hz
2750
2700
Hz 2000
1950
Hz
1650
1600 Hz
1
2
3
OH
3
7.013 13
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
ppm
C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz
9
4
6
7
8
5 1
2 10
3
140
130
120
110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42B
ppm 7.5 3.0
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
ppm
COSY 600 MHz3 OH 3 10
5 6 4 7 8 9 1 3 2
3.0 3.5OH
3.5 4.0 4.5
OCH3
10
4.0 4.5 5.0 5.5 6.0 6.5 7.05 7 6 8 2 1
F1
5.0 5.5 6.0 6.5 7.0
1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
F2ppm 40 ppm58126
HMQC 600 MHz3
407 10
60
128 130
6067.4 7.3 7.2 ppm
80
801
2
F1100 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
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42C 8 6 7 5 1 2 3 OH 3 10
HMBC 600 MHz
ppm 40
7.5
7.4
7.3
7.2
7.1 ppm
4.5
4.0
3.5
3.0
ppm ppm 403
50
5 6 4 7 9 8 1 3 2
5010OH
F16070
OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
10
60
702
80
801
90
90 ppm
F1ppm
125
125
5
8 7
130
130
6
135
135
140
140
94
145 7.5 7.4 7.3 7.2 7.1 ppm 4.5 4.0 3.5 3.0
145 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak 43
Problem 8.43Ax 30 85 95 131 109 182 185 200
100 50 50
100
IR100 90 %Transmittance 80 701 C O 9 10
m/z
150
200
HO
3518
2978
1728
1373 1458
1188
1034
887
H3C 3 11 41
2 5
O 4000
3000
H NMR 600 MHz 68
2000 Wavenumber (cm-1)
1000
7
10
11 8
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
9 7
1260
1240
Hz
780
760
740 Hz
2 OH 5
4
4.513 13
4.0
3.5
3.0
2.5
2.0
1.5
ppm
C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz
7 3 1 6
9
2
4
5 11
8
10
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.40A
ppm 5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
COSY 600 MHz11 10 4 5 2 8
1.5 2.0 2.5
1.5 2.0 2.5 3.06
F1
3.0 3.5 4.0 4.5
3.5 4.0
OH
9
4.57
F2ppm
HMQC 600 MHz10
20 40 60 80HO H3C 3 11 4 2 5 6 7 8 1 C O O 9 10
2011
8 5 4 2 9 3
40 60 80 100 120 140 1601 6
F1 100120 140 160
7
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.43C
HMBC 600 MHz7 9 8 OH 2 5 4 10 11
ppm10
20 30 40 50 60 709 11
8 5 4 2
3
F180F1
90 100 110 120 130 140
HO H3C 3 11 4 2 5 6 7 8 1 C O O 9
10
7
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
6
150 160 1701
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
CHAPTER 8 ASSIGNED PROBLEMS
MASS121 % of Base Peak
Problem 8.44A
100136
50
65
93
149
178
50
100
IR100 %Transmittance
m/z
150
50
3325
2962
1597 1658
1173 1211 1281
841
40001
3000
H NMR 600 MHz3 2
2000 Wavenumber (cm-1)
1000
9 7 6 OH
8
8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm13 13
3.0
2.5O5 1 2 3 4 6 7
2.08 9
1.5
ppm
C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz
2 5 4
3 1
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
6
8 7
9
200
180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44B
ppm 1 2 3 4 5 6 7 8
8
7
6
5
4
3
2
1
ppm 1
COSY 600 MHz9 8 7 6
O5 1
6 7 2 3 4
8 9
2 3 4 5 6OH
F1
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
7 8
3 2
F2ppm
HMQC 600 MHz9
20
207 6
8
40
40
60
60
F1 80100
80
1003
120
1202
8
7
6
5
4
3
2
1
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44C 2 3 6 OH 7 8
HMBC 600 MHz9
ppm
8.0
7.5
7.0
ppm
3.0
2.5
2.0
1.5
1.0
ppm ppm
15O6 5 1 2 7 8 9
15
9
20
208
F1254
3
257
30
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
30
35
356
ppm 120 130 140 150 160 170 180 190 200 210 8.0 7.5 7.0 ppm 3.0 2.5 2.0 1.5 1.0
ppm 120 130 140 150 160 170 180 190 200 210 ppm5 4 1
3
2
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS68 % of Base Peak
Problem 8.45A
100108
50 0
53 79 93 125 153 151 168
50 100
IR
100 m/z
150
%Transmittance
50
2893 2962 3078
2669
1705
1412 1442
1242
887 933
30001
H NMR 600 MHz7 3
2000 Wavenumber (cm-1) 5,4 7 4
1000
5 1 10
2900
2850
Hz
1600
1550
Hz
1200
1150
1100
1050
Hz
x64
9
OH
1213 13
ppmH
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
9 C/DEPTC C/DEPT NMR 150.9 MHz H2 NMR 600 MHz 3 1 7 8 2 6 10 5 4
HO
CH3
O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 Mol. Wt.: 168 8
9
3
7 6
5 10 4 1
2
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.45B
ppm
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
COSY 600 MHz10
1.5 2.0 2.5
1.5 2.0 2.53 54 5,4 7 7
1
F1 3.03.5 4.0 4.5 5.0
3.0 3.5 4.0 4.59
5.0
F2ppm 20 409
HMQC 600 MHz204 1 10 5 7 3
H2C1 7 8 2
H3 6 10 4 5
40 60 801 10
O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid ppm 80 C10H16O2 M Wt.: 168 ol.
HO 60
CH3
F1
100 120 140 160
20
100 120 140 160
9
30
40
50
1803.0 2.5 2.0 1.5 ppm
180
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.45C
HMBC 600 MHz9 3ppm 5.0 4.8 ppm
1 72.4 2.2
10
7
5,4
41.8
51.6 1.4 1.2 ppm
2.6
2.0
420
1259
H2C 301 7 8 2
10H3 6 10 4 5
5
HO 35
CH3
F1 O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 40 Wt.: 168 Mol.6
7
45
50
3
ppm
9 2 85.0 4.8 ppm 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm
150
F2
CHAPTER 8 ASSIGNED PROBLEMS
MASS% of Base Peak
105
Problem 8.46A
100 5053 65 91 122 133 151 148 166
77
50
60
70
80
90
100
110 m/z
120
130
140
150
160
IR%Transmittance
100787
1365 1466
503332 2916
1049
40001
3000
H NMR 600 MHz4
2000 Wavenumber (cm-1)
1000
10 9 9 5 1
2180
2160 Hz
1440
1420
1400
1380
1360
1340
1320
1300
1280
1260
1240
1220 Hz
7 3 11 OH 4
8
5.013
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
C/DEPT NMR 150.9 MHz10 11
CH2CH2OH2 1 8 9 5 6 7 4 3
3 2
11
Nopol C11H18O M Wt.: 166 ol.
1
5 10
9
4 7 8
6
140
130
120
110
100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.46B
ppm 5.5 1.0 1.5 2.0 2.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
COSY 600 MHz8
1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.54
4 7 5 10 9
F1 3.03.51 OH
11
4.0 2 4.5 5.0 5.5
3
F2ppm 201 10 11
HMQC 600 MHz
CH2CH2OH2 3 8 9 5 6 7 4
206
8 7
40
40
1
60
F180
Nopol C11H18O M Wt.: 166 ol.
60ppm 30
11
4 9 6 10 52.5 2.4 2.3 2.2 2.1 ppm
80
35
10040
100
120 5.5 2OH
120 ppm
3
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.46CINADEQUATE 600 MHz INADEQUATE 150.9 MHz
2Hz -15000 -10000 -5000
3
11
1
-15000 -1000010 11
CH2CH2OH2 1 8 6 5 7 4 9 3
-5000 0 5000 10000 15000
F1
0
5000 10000 15000 140 130 120 110 10
Nopol C11H18O M Wt.: 166 ol.100 90 80 70 60 7 50 40 30 20
1Hz -16000 -14000 -12000 -10000 -8000 -6000
5
6
F2
ppm
9 4
8
-16000 -14000 -12000 -10000 -8000 -6000 -4000 -2000 0 2000 4000 45 40 35 30 25 20 ppm
F1-4000 -2000 0 2000 4000
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47A
MASS% of Base Peak
105
CI Reagent gas methane277
100 100 5077 136 154
FM (found) = 277.1083 by CI305 317
50 200 250
50
100
150
IR100
m/z
m/z
300
2877 2939
%Transmittance
3456
50
717
1072
1712 1751
1281
40001
3000
H NMR 600 MHz3 4
2000 Wavenumber (cm-1)
1000
2
6
9
12
10 10OH
7
4800
4700
4600
4500 Hz 3300
3200 OO 13
3100
3000 Hz
1500
1400
1300
Hz
11
8 12
O10
9 8 6 7 11
12
C O O O C 51
O O2250 2200 Hz 1750 1700 Hz
CH2OH
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
CHAPTER 8 ASSIGNED PROBLEMS 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 2.5O O 13
ppm
COSY 600 MHZ7
3O
9 10 6 8 7 11
12
311
4 14 3
C O 52
CH2OH
4
F1 5-(Benzoyloxy)hexahydro-4(hydroxymethyl)C15H16O5 Mol. Wt.: 276
5
5
9 6
6O C O O HOH2C O
6
7
74 3 2
8
8
ppm 2.5 2.5
COSY 600 MHZ7 10 12 10 12 8
3.0
3.0
3.5
3.511
F14.0 4.0
4.5
4.5
5.0
5.0
9 6
5.5 5.5 5.0 4.5 4.0 3.5 3.0 2.5
5.5 ppm
F2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47C13
C/DEPT NMR 150.9 MHz
1130 129 ppm
2 3 477.5 77.0 ppm
9
6
11
7
8 1012
13180
5170
2
160 3
150
140
130
120
110
100
90
80
70
60
50
40 ppm
4
6
9
11
HMQC 600 MHz7
ppmO
409
O 1310 8 6 7
O O O O
C
12 8 10 13 7 11 13 6 12 8 12 10 10 9
12
50O
60 704 3
C O 51 2
11
CH2OH
OH HOH2C
F1 5-(Benzoyloxy)hexahydro-480 (hydroxymethyl)C15H16O5 Mol. Wt.: 276
90 100 110
ppm 35
12 10 83.0 2.9 2.8 2.7 2.6 2.5 2.4 ppm
40
120
3 2 4
130
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
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47D 2 4
HMBC 600 MHz3 6 9 11 12 8 10 7 OH
ppm
8.2
8.0
7.8
7.6
7.4 ppm
5.0
4.5
4.0
3.5
3.0
2.5
ppm
40O 139
O
12 10 8
50O C
10 6 5 O
12 8 7 11
7 11
CH2OH
604
1 2 3
70
5-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276
6 9
80
F1ppm 130
1 4
3 2
140
150
160
5170
13180 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