Compound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below. (a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum. (b) Based on the information provided, determine the structure of compound D.

Principles of Instrumental Analysis
7th Edition
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Chapter19: Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
Problem 19.23QAP
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Compound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below.

(a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum.

(b) Based on the information provided, determine the structure of compound D.

3H
1H NMR Spectrum
1H
2H
1H
(ppm)
Expansion of H NMR Spectrum
Mule
Ppm)
epm)
(Ppm)
Expansion of 'H NMR Spectrum
(Ppm)
(Ppm)
678.37
2808.72
06'949
SS'699
663.30
657.41
2048.35
16'SS9
2042.10
90'O59
648.22
2035.15
2032.54
2026.66
202041
295.25
68'L87
280.54
Transcribed Image Text:3H 1H NMR Spectrum 1H 2H 1H (ppm) Expansion of H NMR Spectrum Mule Ppm) epm) (Ppm) Expansion of 'H NMR Spectrum (Ppm) (Ppm) 678.37 2808.72 06'949 SS'699 663.30 657.41 2048.35 16'SS9 2042.10 90'O59 648.22 2035.15 2032.54 2026.66 202041 295.25 68'L87 280.54
IR Spectrum
1600 cm"
波数/cm
DEPT-135
DEPT-90
C NMR Spektrumispectrum
CDa,
100
100
100
100
100
100
Ppm
-8
Transcribed Image Text:IR Spectrum 1600 cm" 波数/cm DEPT-135 DEPT-90 C NMR Spektrumispectrum CDa, 100 100 100 100 100 100 Ppm -8
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