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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro181

Which of the following statements about the Birch reduction (Na, liquid , ethanol) are correct?

  1. ABenzene gives cyclohexa-1,4-diene.
  2. BIn the product from anisole the OMe group is on a double-bond carbon.
  3. CIn the product from benzoic acid the carbon bearing COOH is .
  4. Dtert-Butylbenzene gives 1-tert-butylcyclohexa-2,5-diene as the main product.

Answer: A, B, C

Benzene gives the 1,4-diene, donors like OMe remain on sp2 carbons, and the acceptor COOH ends up on an sp3 carbon. An alkyl group such as tert-butyl is a donor, so it stays on a double-bond carbon and the product is 1-tert-butylcyclohexa-1,4-diene. Hence option 4 is wrong.
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