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Wolff-Kishner Reduction

Wolff-Kishner Reduction (Reduction.) Converts c1ccc(C(=O)C)cc1 to c1ccc(CC)cc1 using NH₂NH₂ (hydrazine), KOH, heat. Conditions: High temperature, ethylene glycol.

Reduction

Reaction details

Name

Wolff-Kishner Reduction

Type

Reduction

Starting Material

c1ccc(C(=O)C)cc1

Product

c1ccc(CC)cc1

Reagents

  • NH₂NH₂ (hydrazine)

  • KOH

  • heat

Conditions

High temperature, ethylene glycol

Mechanism
  1. Smiles

    c1ccc(C(=O)C)cc1

    Description

    Acetophenone

  2. Smiles

    c1ccc(C(=NN)C)cc1

    Description

    First forms hydrazone

  3. Smiles

    c1ccc(CC)cc1

    Description

    Then loses N₂ under base/heat

Tips

  1. Basic conditions - alternative to Clemmensen

  2. Use for base-stable, acid-sensitive compounds

  3. Mechanism: hydrazone → loss of N₂

Related Reactions

  • clemmensen-reduction

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Reactions

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Substitution

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