Wolff-Kishner reduction
Abstract
The Wolff-Kishner reaction enables the reduction of ketones or aldehydes into alkanes using hydrazine and a strong base such as potassium hydroxide.
Keywords
Reduction, Ketone, Aldehyde, Alkane
Category
Aldehyde/Ketone
Mechanism
First, the ketone (or aldehyde) reacts with hydrazine to form the corresponding hydrazone. Secondly, the base deprotonates the hydrazone to generate an anionic intermediate. Electron rearrangement then leads to the protonation of the carbon in the α-position of the hydrazone by water. Repetition of the hydrazone deprotonation and α-carbon protonation results in the formation of the corresponding alkane with elimination of nitrogen gas.
