SN2 reactions takes place with inversion of configuration, while SN1 reaction takes place with racemization. The following substitution reaction however, occurs with complete retention of configuration. Propose a mechanism. CH, CH, но 1. 1% NAOH, H,0 он Br HO 2. Н,о

SN2 reactions takes place with inversion of configuration, while SN1 reaction takes place with racemization. The following substitution reaction however, occurs with complete retention of configuration. Propose a mechanism. CH, CH, но 1. 1% NAOH, H,0 он Br HO 2. Н,о

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.31P

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

SN2 reactions takes place with inversion of configuration, while SN1 reaction
takes place with racemization. The following substitution reaction however,
occurs with complete retention of configuration. Propose a mechanism.
CH3
CH3
HO
1. 1% NaOH, H,0
OH
Br
но
2. Н,о

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