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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3161

Optically pure (S)-2-bromopropanoate ion is hydrolysed in aqueous NaOH. Select the correct statement(s).

  1. AAt high the direct SN2 attack by external hydroxide competes and the proportion of (R)-lactate formed increases.
  2. BAt low the main product is (S)-lactate, formed with net retention.
  3. CRetention arises because hydroxide displaces bromide from the front side in a single SNi step.
  4. DThe retention arises from two successive SN2 inversions: carboxylate displaces bromide to give an alpha-lactone, and the lactone is then opened by water or hydroxide.

Answer: A, B, D

Low hydroxide concentration favours the intramolecular route (two inversions, retention). High hydroxide concentration allows bimolecular attack of on the C-Br carbon, which inverts; so some (R)-lactate forms. A front-side single-step displacement is not a viable path, so the last statement is false.
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