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🧪 Chemistry  ·  Haloalkanes & Haloarenes  ·  NEET & JEE

When optically active 2-bromooctane is hydrolysed under S<sub>N</sub>1 conditions, the product is:

Answer: a largely racemised mixture.

  • A a single product with full retention
  • B a single product with full inversion
  • C a largely racemised mixture
  • D an achiral meso product

Correct answer: C. a largely racemised mixture

Explanation: The planar carbocation of S<sub>N</sub>1 is attacked from both faces, giving substantial racemisation rather than a single enantiomer.

SN2: one stepNu-CX-backside attackNuC+ X-Inversion of configuration(Walden inversion)SN1: two stepsCX-slow: leaving group exits+CcarbocationNu-Planar intermediate givesracemisation (both faces attacked)

SN2 proceeds in a single step with backside attack and inversion of configuration, while SN1 forms a planar carbocation intermediate first, leading to racemisation.

Concept context

Study carbon-halogen compounds: how they are made, how they react via SN1/SN2 and elimination, their stereochemistry, and their environmental impact.

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