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Wittig Reaction

 A property of carbonyl compounds
 Involves the conversion of aldehydes
and ketones to alkenes with the help of
phosphorous ylides
Carbonyl   Ylide   Alkene
compound
Ylide
• A molecule with adjacent opposite
  charges
• Prepared from alkyl halides with
  triphenylphosphene
Mechanism
• Step 1-The negative carbon of the ylide
  attaches with carbonyl carbon to form
  betaine, a molecule with non-adjacent
  opposite charges

   +S -S         + -                     -
   C==O + C6H5)3 P----CR2           C----O
                                       +
                                  R2C--P(C6H5)3
• Step 2
  Betaine undergoes elimination of triphenyl
  phosphine oxide to give alkene
        -                      C-----O
   C----O
      +                      R2C------P(C6H5)3
 R2C--P(C6H5)3




                    (C6H5)3P==O   +      C==CR2
Applications
• Preparation of alkenes from aldehydes and
  ketones e.g. acetone recats with ylide to form 2,
  methyl propene

     CH3
                          +   -
           C==O + C6H5)3 P----CH2
    CH3



                                           CH3


                    (C6H5)3P==O      +     C==CH2
                                     CH3

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Wittig reaction

  • 1. Wittig Reaction  A property of carbonyl compounds  Involves the conversion of aldehydes and ketones to alkenes with the help of phosphorous ylides
  • 2. Carbonyl Ylide Alkene compound
  • 3. Ylide • A molecule with adjacent opposite charges • Prepared from alkyl halides with triphenylphosphene
  • 4. Mechanism • Step 1-The negative carbon of the ylide attaches with carbonyl carbon to form betaine, a molecule with non-adjacent opposite charges +S -S + - - C==O + C6H5)3 P----CR2 C----O + R2C--P(C6H5)3
  • 5. • Step 2 Betaine undergoes elimination of triphenyl phosphine oxide to give alkene - C-----O C----O + R2C------P(C6H5)3 R2C--P(C6H5)3 (C6H5)3P==O + C==CR2
  • 6. Applications • Preparation of alkenes from aldehydes and ketones e.g. acetone recats with ylide to form 2, methyl propene CH3 + - C==O + C6H5)3 P----CH2 CH3 CH3 (C6H5)3P==O + C==CH2 CH3