Chapter 19.SE, Problem 53MP

Interpretation Introduction

Interpretation:

An epoxyketone is converted into an allylic alcohol when treated with hydrazine in Wharton reaction. A mechanism for the reaction is to be proposed.

Concept introduction:

The reaction involves the formation of hydrazone, abstraction of a proton by a base, opening of epoxide ring and protonation of the oxyanion to yield an enol intermediate. The abstraction of a proton from the intermediate, loss of nitrogen and protonation of the carbanion formed will lead to the product required.

To show:

A mechanism for the Wharton reaction in which an epoxyketone is converted into an allylic alcohol when treated with hydrazine.