A compound with molecular formula C7H140 exhibits the following 13C NMR spectra: Broadband-decoupled 220 200 180 160 140 120 100 80 60 40 20 0 DEPT-90 220 200 180 160 140 120 100 80 60 40 20 0 DEPT-135 220 200 180 160 140 120 100 80 60 40 20 0 Chemical Shift (ppm) Several structures are consistent with these spectra. To determine which structure is correct, a 'H NMR spectrum was acquired which exhibits six signals. One of those signals is a singlet at 1.9 ppm with an integration of 3, and another of the signals is a doublet at 0.9 ppm with an integration of 6. Using this information, identify the correct structure of the compound.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter13: Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
Problem 13.27P: The 13C-NMR spectrum of 3-methyl-2-butanol shows signals at 17.88 (CH3), 18.16 (CH3), 20.01 (CH3),...
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A compound with molecular formula C7H140 exhibits the following 13C NMR spectra:
Broadband-decoupled
220
200
180
160
140
120
100
80
60
40 20
0
DEPT-90
220
200
180
160
140
120
100
80
60
40 20 0
DEPT-135
220
200
180 160
140
120
100
80
60
40
20
0
Chemical Shift (ppm)
Several structures are consistent with these spectra. To determine which structure is correct,
a 'H NMR spectrum was acquired which exhibits six signals. One of those signals is a singlet at
1.9 ppm with an integration of 3, and another of the signals is a doublet at 0.9 ppm with an
integration of 6. Using this information, identify the correct structure of the compound.
Transcribed Image Text:A compound with molecular formula C7H140 exhibits the following 13C NMR spectra: Broadband-decoupled 220 200 180 160 140 120 100 80 60 40 20 0 DEPT-90 220 200 180 160 140 120 100 80 60 40 20 0 DEPT-135 220 200 180 160 140 120 100 80 60 40 20 0 Chemical Shift (ppm) Several structures are consistent with these spectra. To determine which structure is correct, a 'H NMR spectrum was acquired which exhibits six signals. One of those signals is a singlet at 1.9 ppm with an integration of 3, and another of the signals is a doublet at 0.9 ppm with an integration of 6. Using this information, identify the correct structure of the compound.
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