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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro031

Anisole is reduced by Na/liquid /ethanol and the product is warmed with aqueous HCl, which hydrolyses the enol ether and also conjugates the double bond. The final product is

  1. Acyclohex-3-en-1-one
  2. Bcyclohexanone
  3. Ccyclohex-2-en-1-one
  4. Dphenol

Answer: C

Birch gives 1-methoxycyclohexa-1,4-diene. Acid hydrolysis of the enol ether gives cyclohex-3-en-1-one, which isomerises under the stronger acidic conditions to the conjugated cyclohex-2-en-1-one.
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