CH3 A, C3H180 CH2 CH CDCI3 TMS 220 200 180 160 140 120 100 80 60 40 20 8c (ppm)

Chemistry In Focus
6th Edition
ISBN:9781305084476
Author:Tro, Nivaldo J., Neu, Don.
Publisher:Tro, Nivaldo J., Neu, Don.
Chapter18: The Chemistry Of Food
Section: Chapter Questions
Problem 51E
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Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens’ test. The IR

spectrum of A has a strong band near 1710 cm−1 . The broadband carbon NMR spectrum of A is given below.

  1. a)Propose a structure for A and explain how your structure fits the spectral data.
  1. b) Propose a mechanism for this reaction.
CH3
A, C3H1;0
CH2
CH
CDCI3
TMS
220
200
180
160
140
120
100
80
60
40
20
8c (ppm)
Transcribed Image Text:CH3 A, C3H1;0 CH2 CH CDCI3 TMS 220 200 180 160 140 120 100 80 60 40 20 8c (ppm)
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