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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro179

Anisole is reduced with Na in liquid and ethanol, and the crude product is then stirred briefly with cold, dilute aqueous oxalic acid so that no double-bond migration occurs. The major product is

  1. Aphenol
  2. Bcyclohexanone
  3. Ccyclohex-2-en-1-one
  4. Dcyclohex-3-en-1-one

Answer: D

Birch reduction gives 1-methoxycyclohexa-1,4-diene, an enol ether. Mild acid hydrolysis converts the enol ether carbon to C=O, leaving the other double bond at the position originally 1,4 to it, which is the beta,gamma-unsaturated ketone cyclohex-3-en-1-one. Only strong acid with heat would isomerise it to the conjugated cyclohex-2-en-1-one.
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