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JEE Main levelSingle correct optionDifficulty 2 of 3ro240

The compound shown is subjected to Birch reduction (, liquid , ethanol) and then neutralised. Which structure is the major product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The compound is benzoic acid. An electron-withdrawing group such as is attached to an sp3 carbon in the Birch product (reduction at the ipso and para carbons), giving cyclohexa-2,5-diene-1-carboxylic acid. The isomers with the acid on a vinyl carbon are the donor-substituent pattern.
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