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Question

(R)-2-Bromobutane is allowed to react with NaI in acetone. The product formed is :


  1. trans-2-butane

  2. (±)-2-iodobutane

  3. (S)-2-iodobutane

  4. (R)-2-iodobutane


Solution

The correct option is C

(S)-2-iodobutane


I is a capable nucleophile. The given substrate - a secondary alkyl bromide - has a good enough leaving group. The solvent is polar aprotic and overall everything is conducive for an SN2. Now let us explore the stereochemical implications; in SN2 reactions, at the carbon where substitution happens, inversion of configuration occurs because of the concerted nature of the mechanism. Therefore (R)-2-Bromobutane on treatment with NaI in acetone gives (S)-2-iodobutane.

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