Wolff-Kishner Reduction: Definition, Mechanism, Synthetic Applications, Limitations

Wolff-Kishner reduction
Wolff-Kishner reduction

Wolff-Kishner reduction was discovered by Nicolai Kishner in 1911 and Ludwig Wolf in 1912. It involves heating carbonyl compounds with hydrazine and base to convert them to hydrocarbons. In this reaction, aldehyde and ketone react with hydrazine to produce hydrocarbon in presence of base.

Wolff Kishner reduction

Mechanism of Wolff Kishner reduction

Step 1: The electrophilic addition of hydrazine to C=O to produce hydrazone.

Wolff-Kishner reduction

Step II: Addition of base

Wolff-Kishner reduction
Step III: Removal of nitrogen
Wolff-Kishner reduction

Applications of Wolff Kishner reduction

Wolff Kishner reduction is used for,

  1. Production of hydrocarbon from carbonyl compounds
  2. Synthesis of long-chain alkyl chain to the benzene ring
  3. Polycyclic aromatics and aromatics with side hydrocarbon chains

Some examples of sythetic applications

I. Synthesis of camohor from camphane

Synthesis of camohor from camphane

II. Synthesis of pyrrole

Synthesis of pyrrole


  1. Wolff-Kishner reduction reaction needs high temperature.
    • Sometimes double bond migration occurs instead of the expected mechanism of the reaction to give undesirable products like alpha, and beta-unsaturated carbonyl compounds.


  1. Morrison, R. T., & Boyd, R. N., Organic chemistry, Allyn and Bacon, Inc. 1987.
  2. March, J., Advanced Organic Chemistry, Wiley Eastern Limited, 1986.
  3. Skyes, P., A Guide Book to Mechanism in Organic Chemistry, Second edition, Orient Longman Ltd., 1988

About Author

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Kabita Sharma

Kabita Sharma is a graduate student from the central department of chemistry, Tribhuvan University. She has been actively involved in research related to natural products, computational chemistry, and nanochemistry. She is currently working on enzyme assay, molecular docking, and molecular dynamic simulation.

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