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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro243

The compound shown is treated with Birch conditions (, liquid , ethanol) and the crude diene is stirred with dilute aqueous acid at room temperature (mild hydrolysis only, no isomerisation of the double bonds). Which structure is the final organic product?

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

Answer: C

The compound is 4-methylanisole. Birch reduction leaves both donor groups on sp2 carbons, giving 1-methoxy-4-methylcyclohexa-1,4-diene. Mild acid hydrolyses the enol ether to the ketone and the other double bond stays in the ring, giving 4-methylcyclohex-3-en-1-one. Strong acid would isomerise it to the conjugated enone (the second option), and the saturated ketone and phenol need extra steps.
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