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Chapter 22: Q22-62E (page 752)

Ketones react slowly with benzene selenenyl chloride in the presence of HCl to yield a-phenyl seleno ketones. Propose a mechanism for this acid-catalyzed a-substitution reaction.

Short Answer

Expert verified

The reaction mechanism starts with keto-enol tautomerism and ends with the loss of a proton.

Step by step solution

01

Acid-catalyzed enol formation

The alpha hydrogen of the ketone participates in enolisation in the presence of acid HCl.

Acid catalysed enolisation

02

Explanation

The attack at enol 蟺 electrons on benzene selenenyl chloride with loss of

Cl-ith the loss of proton by the attack of Base in the solution.

The final product

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