A rather interesting example of the Wolff rea | vedclass

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Question

(A) The reaction is an intramolecular Wolff rearrangement. When $2$-diazocyclohexanone is irradiated with light,it loses nitrogen gas $(N_2)$ to form

Vedclass · Accepted Answer

Cyclopentanecarboxylic acid methyl ester

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(A) The reaction is an intramolecular Wolff rearrangement. When $2$-diazocyclohexanone is irradiated with light,it loses nitrogen gas $(N_2)$ to form a carbene intermediate. This carbene undergoes a ring contraction via a $1,2$-alkyl shift to form a ketene intermediate (cyclopentylketene). Subsequently,the nucleophilic attack of methanol $(CH_3OH)$ on the ketene carbonyl carbon leads to the formation of the final product,which is methyl cyclopentanecarboxylate (cyclopentanecarboxylic acid methyl ester).

$A$ rather interesting example of the Wolff rearrangement with $2$-diazocyclohexanone in methanol is given below. Identify the major product.

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