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

1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]

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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