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

 CHAPTER 8 ASSIGNED PROBLEMS
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
H NMR
H NMR 300 MHz 7
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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
2
1
Br 4
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

 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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

 CHAPTER 8 ASSIGNED PROBLEMS
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
 CHAPTER 8 ASSIGNED PROBLEMS
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