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JEE Main levelSingle correct optionDifficulty 2 of 3ro025

Benzoic acid is subjected to Birch reduction (Na, liquid , ethanol), then acidified. The product is

  1. Acyclohexa-1,4-diene-1-carboxylic acid
  2. Bcyclohexa-2,4-diene-1-carboxylic acid
  3. Ccyclohexa-2,5-diene-1-carboxylic acid
  4. Dcyclohexanecarboxylic acid

Answer: C

An electron-withdrawing group ends up on an sp3 carbon (the ipso carbon is protonated and the para carbon also receives H). The double bonds are at C2-C3 and C5-C6: cyclohexa-2,5-diene-1-carboxylic acid.
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