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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro268

The compound shown is heated with aqueous (excess), then acidified with . Select ALL correct statements.

  1. APhenol is obtained after acidification.
  2. BEthanoic acid is obtained after acidification.
  3. CMethanol is formed.
  4. DTwo moles of are consumed per mole of the compound, because the phenol produced is acidic.

Answer: A, B, D

The compound is phenyl acetate. Saponification cleaves the acyl-oxygen bond: acetate and phenoxide form, and the phenol (pKa about 10) is deprotonated by a second mole of , so 2 mol of base are used. Acidification liberates ethanoic acid and phenol. No methanol is involved because the alkoxy part is phenol, not a methyl group.
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