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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro272

The ester shown is heated with aqueous and then acidified. Which structure is the chiral alcohol obtained?

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

Answer: B

The compound is (R)-sec-butyl acetate. Saponification proceeds by attack of hydroxide on the carbonyl carbon and cleavage of the acyl-oxygen bond; the C-O bond at the stereocentre is never broken, so the configuration is retained and (R)-butan-2-ol forms (the priority order O > ethyl > methyl > H is unchanged). Inversion (the enantiomer) would require attack at the alkyl carbon, which does not happen.
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