Exercise plus Solution Quick overview
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118120122124126128130132134136138140142144
ppm13
C
117.95
122.76
136.59
136.97
137.25
140.12
ppm
C
10
H
8
measured in CDCl
3
Deduce the structure!
13
C{
1
H} NMR spectrum
measured at 125.70{488.84} MHz
2.15
2.00
1.08
0.98
2.08
Inte-
gral
7.17.27.37.47.57.67.77.87.98.08.18.28.38.4 ppm1
H
3576.56
3586.40
3596.15
3702.67
3706.41
3786.59
3796.53
3806.38
3956.38
3960.13
3963.83
4175.41
4184.71
Hz
1
H NMR spectrum
measured at 488.84 MHz
7.27.47.67.88.08.28.4
ppm
1
H
120
125
130
135
140
13
C
136.2
136.4
136.6
137.0
137.2
137.4
137.6
137.8
138.0
13
C
7.67.77.87.98.08.28.38.4
1
H
ppm
1
H/
13
C HSQC
measured at 499.84/125.70 MHz
120
125
130
135
140
13
C
7.17.27.37.47.57.67.87.98.08.18.28.38.4
1
H
ppm
1
H/
13
C HMBC
measured at 499.84/125.7 MHz
7.27.47.67.88.08.28.4
1
H
ppm
7.2
7.4
7.6
7.8
8.0
8.2
8.4
1
H
1
H TOCSY
measured at 499.84 MHz
80ms mixing time
Usually one gets stuck with the solution
“naphthalene” quickly after seeing the molecular
formula C
10
H
8
.
The real challenge here is to break out of this
mental cage.