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JEE Advanced levelSingle correct optionDifficulty 3 of 3el274

The drug shown is boiled with excess aqueous NaOH, then the cooled mixture is acidified with dilute HCl. Which structure shown is the aromatic compound that separates?

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

Answer: B

The compound shown is aspirin. NaOH hydrolyses the ester and forms the disodium salt of salicylic acid (plus sodium acetate). Acidification re-protonates both groups, so salicylic acid is released and separates as a solid. Aspirin is not regenerated, no decarboxylation to phenol occurs, and the anion is not present after acidification.
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