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Wittig reaction

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  • 1. Wittig Reaction A property of carbonyl compounds Involves the conversion of aldehydesand ketones to alkenes with the help ofphosphorous ylides
  • 2. Carbonyl Ylide Alkenecompound
  • 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

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