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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro053

Which statements about ester hydrolysis are correct?

  1. AAlkaline hydrolysis is effectively irreversible because the carboxylic acid formed is converted to its carboxylate.
  2. BAcid-catalysed hydrolysis of ethyl acetate is reversible.
  3. CIn BAC2 hydrolysis the reaction proceeds through a tetrahedral intermediate.
  4. DAlkaline hydrolysis of ethyl 4-methylbenzoate is faster than that of ethyl 4-nitrobenzoate.

Answer: A, B, C

The carboxylate cannot be attacked by alkoxide, so base hydrolysis goes to completion (A). Acid hydrolysis equals the reverse of Fischer esterification (B). BAC2 proceeds through addition-elimination (C). The nitro group makes the carbonyl carbon more electrophilic and speeds attack, so D is false.
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