When 2-methyleyclohexanone is treated with pyrrolidine, two isomeric enamines are formed. H* + H20 A (85%) В (15%) Why is enamine A with the less substituted double bond the thermodynamically favored product? (You will find it helpful to examine the models of these two enamines.)

When 2-methyleyclohexanone is treated with pyrrolidine, two isomeric enamines are formed. H* + H20 A (85%) В (15%) Why is enamine A with the less substituted double bond the thermodynamically favored product? (You will find it helpful to examine the models of these two enamines.)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 59AP

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When 2-methyleyclohexanone is treated with pyrrolidine, two
isomeric enamines are formed.
H*
+ H20
A (85%)
В (15%)
Why is enamine A with the less substituted double bond the
thermodynamically favored product? (You will find it helpful to
examine the models of these two enamines.)

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