An unknown compound A with molecular formula C6H1004 shows significant fragment peaks at m/z 146, 115, 87 and 59 (base peak) in its mass spectrum. (a). Analyse the following spectrocopic data with appopriate explanations. Η ΝMR (200 MHz, CDCI3) °C NMR (50 MHz, CDCI3) IR DEPT-135 (v, cm*) 1.23, d, 3H 3.31, q, 1H 13.5 (positive) 47.2 (positive) 53.5 (positive) 13.5 47.2 1737 3.82, s, 6H 53.5 171.8 (b). Propose the fragmentation that indicates the base peak at m/z 59 of compound A (c). With aid of the data in (a)., give the most plausible structure of compound A

Organic Chemistry
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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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An unknown compound A with molecular formula C6H1004 shows significant
fragment peaks at m/z 146, 115, 87 and 59 (base peak) in its mass spectrum.
(a). Analyse the following spectrocopic data with appopriate explanations.
Η ΝMR
(200 MHz, CDCI3)
T°C NMR
(50 MHz, CDCI3)
IR
DEPT-135
(v, cm1)
1.23, d, 3H
3.31, q. 1Н
3.82, s, 6H
13.5 (positive)
47.2 (positive)
53.5 (positive)
13.5
47.2
1737
53.5
171.8
(b). Propose the fragmentation that indicates the base peak at m/z 59 of
compound A
(c). With aid of the data in (a)., give the most plausible structure of compound
A
Transcribed Image Text:An unknown compound A with molecular formula C6H1004 shows significant fragment peaks at m/z 146, 115, 87 and 59 (base peak) in its mass spectrum. (a). Analyse the following spectrocopic data with appopriate explanations. Η ΝMR (200 MHz, CDCI3) T°C NMR (50 MHz, CDCI3) IR DEPT-135 (v, cm1) 1.23, d, 3H 3.31, q. 1Н 3.82, s, 6H 13.5 (positive) 47.2 (positive) 53.5 (positive) 13.5 47.2 1737 53.5 171.8 (b). Propose the fragmentation that indicates the base peak at m/z 59 of compound A (c). With aid of the data in (a)., give the most plausible structure of compound A
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