Determine Products of Side Chain Oxidation

 

 

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  1. Benzylic C (C next to the benzene ring) is oxidized to benzoic acid (or benzoate under alkaline conditions)
  2. All other C in the side chain are oxidized to CO2 
  3. For side chain oxidation to occur, the benzylic C must contain at least 1 H atom
  4. K2Cr2O7 (H+ or OH) cannot cause side chain oxidation

 

Example:

 

Question. What happens when there exist C=C in the side chain.

 

Answer. It is relatively easier to oxidise a C=C than the benzene side chain. Hence, you have to first perform an oxidative cleavage of the C=C and write down the oxidized product of the fragment not attached to the benzene ring.

Then perform a side chain oxidation to oxidise the remaining fragment to give benzoic acid and CO2.

 

Example: