ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 28, Problem 28.51AP
Interpretation Introduction
Interpretation:
In 1985, two researchers at the University of California, Riverside, carried out the reaction given in Fig. P28.51.The equilibrium mixture contained compound A (22%), a single stereoisomer of B (47%), and a single stereoisomer of C (31%).The stereochemistry of compounds B and C at the carbon marked with the asterisk (*) is to be predicted.
Concept introduction:
Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement. Notably, [3, 3] sigmatropic reaction of allyl vinyl ether is termed as Claisen rearrangement.
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Part II. two unbranched ketone have molecular formulla (C8H100). El-ms showed that
both of them
have a molecular ion peak at m/2 =128. However ketone
(A) has a fragment peak at m/2 = 99 and 72
while ketone (B) snowed a
fragment peak at m/2 = 113 and 58.
9) Propose the most plausible structures for both ketones
b) Explain how you arrived at your conclusion by drawing the
Structures of the distinguishing fragments for each ketone,
including their fragmentation mechanisms.
Chapter 28 Solutions
ORGANIC CHEM +SG +SAPLING >IP<
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Prob. 28.3PCh. 28 - Prob. 28.4PCh. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29APCh. 28 - Prob. 28.30APCh. 28 - Prob. 28.31APCh. 28 - Prob. 28.32APCh. 28 - Prob. 28.33APCh. 28 - Prob. 28.34APCh. 28 - Prob. 28.35APCh. 28 - Prob. 28.36APCh. 28 - Prob. 28.37APCh. 28 - Prob. 28.38APCh. 28 - Prob. 28.39APCh. 28 - Prob. 28.40APCh. 28 - Prob. 28.41APCh. 28 - Prob. 28.42APCh. 28 - Prob. 28.43APCh. 28 - Prob. 28.44APCh. 28 - Prob. 28.45APCh. 28 - Prob. 28.46APCh. 28 - Prob. 28.47APCh. 28 - Prob. 28.48APCh. 28 - Prob. 28.49APCh. 28 - Prob. 28.50APCh. 28 - Prob. 28.51APCh. 28 - Prob. 28.52APCh. 28 - Prob. 28.53APCh. 28 - Prob. 28.54APCh. 28 - Prob. 28.55AP
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