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JEE Advanced levelSingle correct optionDifficulty 3 of 3el272

The compound shown is refluxed with dilute aqueous hydrochloric acid. Which pair of products forms (ignoring protonation state of the amine)?

  1. A4-Ethoxybenzoic acid and ammonia
  2. B4-Ethoxyaniline and acetic acid
  3. C4-Aminophenol and ethyl acetate
  4. DParacetamol and ethanol

Answer: B

The compound shown is phenacetin, an N-aryl acetamide with an aryl ethyl ether. Dilute acid cleaves the amide, which gives 4-ethoxyaniline (as its hydrochloride) and acetic acid. An aryl ether is not cleaved by dilute HCl, so the ethoxy group remains.
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