Propose a mechanism for both parts of the Wolff-Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base catalyzed reduction with evolution of nitrogen gas.

Short Answer

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Cyclohexanone is first converted to hydrazone, which then undergoes base catalyzed reduction to give the cyclohexane.

Step by step solution

01

Wolf-Kishner Reduction

The compound that cannot resist treatment with hot acids can be deoxygenated (loss of oxygen) by using Wolf Kishner reduction. Aldehydes and ketones on being heated with hydrazine H2N-NH2and a strong base like potassium hydroxideKOH at the temperature range of140-200°C form hydrocarbon.

02

Mechanism of Wolf-Kishner Reduction

The mechanism part is shown below.

Step (a) Formation of hydrazone from cyclohexanone.

Step (b) Base catalyzed reduction of hydrazone to cyclohexane with the evolution of nitrogen gas.

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