CHAPTER 8 ASSIGNED PROBLEMS
MASS Problem 8.1
68
55
% of Base Peak 100
41 112
84
50
97
40 50 60 70 80 90 100 110
m/zO
IR
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)
1 1H
NMR 300 MHz 4
H NMR
2
3
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
1313C/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 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
C7H8O2
3398
3005
2947
2839
1601
1493
1284
1149
1041
945
837
768
687
Mol. Wt.: 124
4000 3000 2000 1000
Wavenumber (cm-1)
11H
NMR 300 MHz
H NMR 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
C/DEPT NMR 75.5 MHz
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
MASS Problem 8.3
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
H2C C C CH2
1 2 3
5 CH3
CDCl3 2-Pentyn-ol
3 C5H8O 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
MASS Problem 8.4
75
CI Reagent gas methane
% of Base Peak 100 111 x 30
110
49 M 100 113
99 112 146
61 77 148
50 97 148 75 150
114
50 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 C 3H 5Cl 3
Mol. Wt.: 146
3016
2962
1435
1288
1219
910
717
663
4000 3000 2000 1000
11
Wavenumber (cm-1) 1+3
H
H NMR
NMR 300 MHz
2
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
2
75 70 65 60 55 50 45 ppm
MASS Problem 8.1
68
55
% of Base Peak 100
41 112
84
50
97
40 50 60 70 80 90 100 110
m/zO
IR
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)
1 1H
NMR 300 MHz 4
H NMR
2
3
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
1313C/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 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
C7H8O2
3398
3005
2947
2839
1601
1493
1284
1149
1041
945
837
768
687
Mol. Wt.: 124
4000 3000 2000 1000
Wavenumber (cm-1)
11H
NMR 300 MHz
H NMR 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
C/DEPT NMR 75.5 MHz
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
MASS Problem 8.3
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
H2C C C CH2
1 2 3
5 CH3
CDCl3 2-Pentyn-ol
3 C5H8O 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
MASS Problem 8.4
75
CI Reagent gas methane
% of Base Peak 100 111 x 30
110
49 M 100 113
99 112 146
61 77 148
50 97 148 75 150
114
50 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 C 3H 5Cl 3
Mol. Wt.: 146
3016
2962
1435
1288
1219
910
717
663
4000 3000 2000 1000
11
Wavenumber (cm-1) 1+3
H
H NMR
NMR 300 MHz
2
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
2
75 70 65 60 55 50 45 ppm
