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Wittig Reaction

Wittig Reaction (Carbonyl.) Converts CC=O to CC=C using Ph₃P=CH₂ (ylide).

Carbonyl

Reaction details

Name

Wittig Reaction

Type

Carbonyl

Starting Material

CC=O

Product

CC=C

Reagents
  • Ph₃P=CH₂ (ylide)

Mechanism
  1. Smiles

    CC=O

    Description

    Acetaldehyde

  2. Smiles

    CC=O

    Description

    Ylide attacks carbonyl carbon

  3. Smiles

    CC=C

    Description

    Propene formed, Ph₃P=O byproduct

Tips
  1. Converts C=O to C=C

  2. Ylide made from: Ph₃P + R-X, then base

  3. Stereochemistry controlled by ylide type (stabilized vs unstabilized)

Related Reactions
  • grignard-addition

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