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.

Question

Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate.

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.
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Transcribed Image Text

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.

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