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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3090

Sodium -2-bromopropanoate, , is hydrolysed in dilute aqueous alkali. Assume that the rate-determining step is intramolecular displacement of bromide by the carboxylate oxygen (forming a three-membered alpha-lactone, with inversion), followed by SN2 opening of the lactone by water or hydroxide at the same carbon (another inversion). The net stereochemical result, the CIP descriptor of the lactate product, and the dependence of the rate on are

  1. Aretention; -lactate; rate independent of
  2. Binversion; -lactate; rate independent of
  3. Cretention; -lactate; rate proportional to
  4. Dinversion; -lactate; rate proportional to

Answer: A

Neighbouring-group participation involves two successive inversions at the same carbon, so the net result is retention. The priorities in the bromo compound are and in lactate , the same order, so retention keeps the label: -lactate. Because the slow step is the unimolecular ring closure, the rate does not depend on hydroxide concentration.
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