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Klein and Straumanis Guided
20: Aldehydes and Ketones
20.15: 20.7a Nucleophilic Addition of Hydrazin - The Wolff-Kishner Reaction

20.15: 20.7a Nucleophilic Addition of Hydrazin - The Wolff-Kishner Reaction

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Objectives

After completing this section, you should be able to

write an equation to illustrate the Wolff‑Kishner reduction of an aldehyde or ketone.
identify the product formed from the Wolff‑Kishner reduction of a given aldehyde or ketone.

Key Terms

Make certain that you can define, and use in context, the key term below.

Wolff‑Kishner reduction

Study Notes

After studying this section, you can add yet another method of reducing organic compounds to your growing list of reduction reactions.

Aldehydes and ketones can be converted to a hydrazine derivative by reaction with hydrazine. These "hydrazones" can be further converted to the corresponding alkane by reaction with base and heat. These two steps can be combined into one reaction called the Wolff-Kishner Reduction which represents a general method for converting aldehydes and ketones into alkanes. Typically a high boiling point solvent, such as ethylene glycol, is used to provide the high temperatures needed for this reaction to occur. Note! Nitrogen gas is produced as part of this reaction.