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JEE Main · 2024 · 27 Jan 2024 · Shift 1 · Haloalkanes and Haloarenes

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The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is ;
  1. (A)Retention occurs in reaction and inversion occurs in reaction.
  2. (B)Racemisation occurs in reaction and retention occurs in reaction.
  3. (C)Racemisation occurs in both and reactions.
  4. (D)Racemisation occurs in reaction and inversion occurs in reaction.✓ Correct

Answer: (D)

Solution

In , the leaving group departs first to give a planar carbocation, which the nucleophile can then attack from either face with roughly equal probability — this gives racemisation. In , the nucleophile attacks in a single step from the side opposite the leaving group, forcing inversion of configuration (Walden inversion). So racemisation occurs in and inversion in .

JEE Main · 2024 · 27 Jan 2024 · Shift 1 · Single correct option

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