Wolff-Kishner Reduction: Carbonyl to Alkane

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The ketone is first converted to a hydrazone via the hydrazine (H₂NNH₂) reagent. Click here to view this mechanism. This then undergoes reduction by hot concentrated sodium hydroxide. The reaction works due to the thermodynamic stability of N₂.

H. H. Szmant, H. F. Harnsberger, T. J. Butler and W. P. Barie, J. Am. Chem. Soc., 1952, 74, 2724–2728.