Determine Products of Oxidative Cleavage

 

 

← Back to Alkenes

 

  1. Cleave the C=C
  2. Add O at the end of each dangling C=
  3. Check for H bonded to C on C=O (i.e. aldehydes); Add an O to each H directly bonded to C=O (i.e. convert the aldehyde to a carboxylic acid). If the C on C=O is directly bonded to 2H i.e. H2C=O, the fragment is oxidized completely to CO2
  4. If the conditions for the oxidation is alkaline (i.e. KMnO4/OH–), convert all –COOH to –COO– and CO2 to CO32–

 

Example: Determine the products when 2-methyl-but-2-ene, (CH3)2C=CHCH3 is reacted with hot alkaline KMnO4.