Wittig reaction

 
   
 

The Wittig reaction is an organic reaction used to convert a primary or secondary alkyl halide and aldehyde or ketone to an olefin using triphenylphosphine and base.

 
  Mechanism  
 
  • The alkyl halide is attacked by PPh3 and releases the halogen anion and forms a phosphonium ion.
  • The base is then deprotonated in the alpha position to give a phosphorus ylide. Subsequently, Wittig's reagent attacks the aldehyde or ketone.
  • The oxygen anion attacks the phosphorus atom in an intramolecular attack.
  • Oxophosphetane decomposes to produce an alkene and triphenylphosphine oxide. The formation of a strong P=O bond is the driving force for this reaction.