(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
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(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.

(b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.

(c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.

20-
3500
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1000
Wavenumber (cm-1)
19.4
65.7
22,7
144.0
COMPOUND C
100.7
13C-NMR spectrum
zdo Tdu
to
2H
COMPOUNDC
1H-NMR spectrum
4H
1H
1H
to
100
90
80-
COMPOUND C
70-
Mass spectrum
60-
50
83
40-
30-
20-
69
10-
27
41
15
04
10
15
20 25
30
35
40
45
50
55
60
65
70
75
80
85
90
MIZ
1238
-1644
Transcribed Image Text:20- 3500 3000 2500 2000 1500 1000 Wavenumber (cm-1) 19.4 65.7 22,7 144.0 COMPOUND C 100.7 13C-NMR spectrum zdo Tdu to 2H COMPOUNDC 1H-NMR spectrum 4H 1H 1H to 100 90 80- COMPOUND C 70- Mass spectrum 60- 50 83 40- 30- 20- 69 10- 27 41 15 04 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 MIZ 1238 -1644
50-
40-
30-
20-
COMPOUNDB
IR spectrum
10-
3500
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Wavenumber (cm-1)
|130.0
COMPOUND B
13C-NMR spectrum
191.4
139.9
zdo
to
COMPOUND B
1H-NMR spectrum
100-
80-
COMPOUND C
60-
IR spectrum
40-
20-
3500
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1500
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Wavenumber (cm-1)
Transmittance
Transmittance
1450
Transcribed Image Text:50- 40- 30- 20- COMPOUNDB IR spectrum 10- 3500 3000 2500 2000 1500 1000 Wavenumber (cm-1) |130.0 COMPOUND B 13C-NMR spectrum 191.4 139.9 zdo to COMPOUND B 1H-NMR spectrum 100- 80- COMPOUND C 60- IR spectrum 40- 20- 3500 3000 2500 2000 1500 1000 Wavenumber (cm-1) Transmittance Transmittance 1450
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