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JEE Advanced levelSingle correct optionDifficulty 3 of 3si013

A compound is neutral to litmus, gives no effervescence with and no colour with neutral . Boiling with aqueous NaOH and then acidifying gives benzoic acid, and the alcohol formed does not give iodoform test but its oxidation product gives a silver mirror with Tollens reagent. The compound is

  1. Amethyl benzoate
  2. Bphenyl ethanoate
  3. C4-methylbenzoic acid
  4. Dbenzyl methanoate

Answer: A

A neutral, FeCl3-negative ester excludes the acid and phenolic compounds (phenyl ethanoate would release phenol and 4-methylbenzoic acid effervesces). Benzoic acid as the acid part leaves as the alcohol part, which is not iodoform positive and is oxidised to methanal, which reduces Tollens reagent. So the ester is .
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