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KCET2026ChemistryHaloalkanes and Haloarenes

In S _ N 1 reaction, the alkyl halide that on hydrolysis produces racemic mixture is

Options

  1. ATertiary butyl bromide
  2. B2-bromobutane
  3. CIsopropyl bromide
  4. DMethyl bromide

Correct answer

B. 2-bromobutane

Step-by-step solution

In an S _ N 1 reaction, the formation of a racemic mixture occurs only if the product formed has a chiral center. Tertiary butyl bromide on hydrolysis gives tertiary butyl alcohol, which is achiral. 2-bromobutane on hydrolysis forms a planar secondary carbocation intermediate. The nucleophile (water) can attack from either face of the planar carbocation with equal probability, leading to the formation of d and l enantiomers of 2-butanol. Since 2-butanol has a chiral carbon, a racemic mixture is produced. Isopropyl

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