8.33 C6H10O2
8.34 C10H20O
8.41 C8H10O3
8.42 C10H12O2
8.44 C11H14O2
Problem 8.33A
MASS
% of Base Peak
85
100
50
57
70
70
60
50
IR
114
m/z
110
100
90
80
656
1180
1774
4000
1
972
50
1358
1466
2885
2970
%Transmittance
100
3000
H NMR 600 MHz
3.5
4.0
3.0
2000
Wavenumber (cm-1)
1000
1.0
1.5
2.0
2.5
ppm
13
13
C/DEPTNMR
NMR150.9
600 MHz
C/DEPT
MHz
29
180
160
140
120
100
80
28
60
p pm
40
20
ppm
Problem 8.33B
ppm 4.5
4.0
2.5
3.0
3.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
F1 2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
F2
HMQC 600 MHz
ppm
10
10
20
20
30
30
40
40
ppm
F1 50
50
28
60
60
30
2.0
2.5
1.5 ppm
70
70
80
80
4.5
4.0
3.5
2.5
3.0
F2
COSY 600 MHz
2.0
1.5
1.0
ppm
Problem 8.34A
MASS
% of Base Peak
41
69
100
81
55
95
50
123
109
IR
m/z
100
110
120
130
140
1057
90
156
1381
1450
80
70
60
50
40
138
150
160
50
4000
1
3000
H NMR 600 MHz
2.5
3.0
3.5
4.0
4.5
5.0
2000
Wavenumber (cm-1)
833
2924
3332
%Transmittance
100
1000
1.0
1.5
2.0
ppm
13
13
C/DEPTNMR
NMR 150.9
600 MHz
C/DEPT
MHz
26
130
120
110
25
100
ppm
90
80
70
60
50
40
30
20 ppm
Problem 8.34B
ppm 5.5
5.0
4.5
4.0
3.0
3.5
2.5
2.0
1.5
1.0
ppm
1.0
1.0
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
5.0
5.0
F2
HMQC 600 MHz
ppm
20
20
40
40
60
60
ppm
F1 80
80
20
100
100
30
40
120
120
ppm
2.0 1.5 1.0
5.5
5.0
4.5
4.0
3.5
3.0
F2
COSY 600 MHz
2.5
2.0
1.5
1.0
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
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
COSY 600 MHz
F1
F2
HMQC 600 MHz
ppm
25
25
30
30
35
35
40
40
F1
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
F2
45
ppm
Problem 8.42A
MASS
% of Base Peak
104
100
121
50
131
91
77
164
65
50
60
146
90
80
70
IR
120
100 110
m/z
140
130
160
150
1720
50
4400
4350
Hz
2750
6.0
6.5
7.0
2700
2000
Wavenumber (cm-1)
Hz 2000
5.5
748
H NMR 600 MHz
972
1
3000
1088
4000
1350
1466
2831
2939
3402
%Transmittance
100
1950
5.0
Hz
1000
1650
1600 Hz
3.0
3.5
4.0
4.5
ppm
13
13
C/DEPTNMR
NMR150.9
600 MHz
C/DEPT
MHz
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
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
F1 5.0
5.0
5.5
5.5
6.0
6.0
6.5
6.5
7.0
7.0
F2
HMQC 600 MHz
ppm
40 ppm
40
126
60
60
128
130
7.4
80
7.3
7.2
ppm
80
F1
100
100
120
120
7.5
7.0
6.5
6.0
5.5
5.0
F2
COSY 600 MHz
4.5
4.0
3.5
3.0
ppm
Problem 8.42C
HMBC 600 MHz
ppm
7.5
7.4
7.3
7.2
7.1 ppm
4.5
4.0
3.5
3.0
ppm
ppm
40
40
50
50
60
60
70
70
80
80
90
90
F1
ppm
ppm
125
125
130
130
135
135
140
140
145
7.5
7.4
7.3
7.2
7.1 ppm
F2
4.5
4.0
3.5
3.0
145
ppm
Problem 8.44A
MASS
% of Base Peak
121
100
136
50
93
65
100
50
178
149
IR
150
m/z
50
2000
Wavenumber (cm-1)
8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm
1000
2.0
2.5
3.0
841
H NMR 600 MHz
1173
1211
1281
1
3000
1597
1658
4000
2962
3325
%Transmittance
100
1.5
ppm
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
200
180
160
140
120
100
80
60
40
ppm
Problem 8.44B
ppm
F1
8
7
6
5
4
3
2
1
ppm
1
1
2
2
3
3
4
4
5
5
6
6
7
7
8
8
F2
HMQC 600 MHz
ppm
20
20
40
40
60
60
F1 80
80
100
100
120
120
8
7
6
5
F2
COSY 600 MHz
4
3
2
1
ppm
Problem 8.44C
HMBC 600 MHz
ppm
8.0
7.5
7.0
ppm
3.0
2.5
2.0
1.5
1.0
ppm
ppm
15
15
20
20
25
25
30
30
35
35
F1
ppm
ppm
120
120
130
130
140
140
150
150
160
160
170
170
180
180
190
190
200
200
210
210
ppm
8.0
7.5
7.0
ppm
F2
3.0
2.5
2.0
1.5
1.0

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