The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. CI CO Na+ COH NaOH NaOH HCI THF THF H,O A proposed intermediate It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropa- none shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid.

The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. CI CO Na+ COH NaOH NaOH HCI THF THF H,O A proposed intermediate It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropa- none shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...

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