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.

Question

1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

Answer 1

Question

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.

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