The proton NMR spectrum of a compound with formula C8H14O2 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows medium-sized bands at 3055, 2960, 2875, and 1660 cm-1 and strong bands at 1725 and 1185 cm-1 . Draw the structure of this compound and assign the carbon peaks.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
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Problem 59GP: The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this...
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The proton NMR spectrum of a compound with formula C8H14O2 is shown. The
DEPT experimental results are tabulated. The infrared spectrum shows
medium-sized bands at 3055, 2960, 2875, and 1660 cm-1
and strong bands at
1725 and 1185 cm-1
. Draw the structure of this compound and assign the
carbon peaks.

60
6.8
6.7
4.2
41
40
1.9
1.8
1.7
1.6
15
1.4
1.3
1.2
1.1
10
0.9
Transcribed Image Text:60 6.8 6.7 4.2 41 40 1.9 1.8 1.7 1.6 15 1.4 1.3 1.2 1.1 10 0.9
Assignment
The proton NMR spectrum of a compound with formula C3H14O2 is shown. The
DEPT experimental results are tabulated. The infrared spectrum shows
-1
medium-sized bands at 3055, 2960, 2875, and 1660 cm and strong bands at
1725 and 1185 cm. Draw the structure of this compound and assign the
carbon peaks.
Normal Carbon
DEPT-135
DEPT-90
10.53 ppm
Positive
No peak
No peak
No peak
No peak
12.03
Positive
14.30
Positive
22.14
Negative
No peak
No peak
65.98
Negative
No peak
128.83
136.73
Positive
Positive
168.16
No peak
No peak (C=0)
0.97
2.05
7.92
2.96
65
60
5.5
5.0
4.5
4.0
3.5
3.0
25
20
15
1.0
Transcribed Image Text:Assignment The proton NMR spectrum of a compound with formula C3H14O2 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows -1 medium-sized bands at 3055, 2960, 2875, and 1660 cm and strong bands at 1725 and 1185 cm. Draw the structure of this compound and assign the carbon peaks. Normal Carbon DEPT-135 DEPT-90 10.53 ppm Positive No peak No peak No peak No peak 12.03 Positive 14.30 Positive 22.14 Negative No peak No peak 65.98 Negative No peak 128.83 136.73 Positive Positive 168.16 No peak No peak (C=0) 0.97 2.05 7.92 2.96 65 60 5.5 5.0 4.5 4.0 3.5 3.0 25 20 15 1.0
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