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JEE MainChemistryHaloalkanes and Haloarenes

Given below are two statements : Statement (I) : Nucleophilic substitution of an optically active alkyl halide via the S _ N 1 mechanism always yields a perfectly 50:50 racemic mixture with zero net optical rotation. Statement (II) : In an S _ N 1 reaction, the departing halide ion can temporarily shield the front side of the carbocation, leading to a slightly higher yield of the inverted product compared to the reta

Options

  1. ABoth Statement I and Statement II are true
  2. BStatement I is false but Statement II is true
  3. CBoth Statement I and Statement II are false
  4. DStatement I is true but Statement II is false

Correct answer

B. Statement I is false but Statement II is true

Step-by-step solution

Statement I is false because S _ N 1 reactions of optically active alkyl halides rarely yield a perfect 1:1 racemic mixture. They typically show a slight net optical activity due to an excess of the inversion product. Statement II is true. This occurs due to the formation of an intimate ion-pair, where the leaving group temporarily blocks the front-side attack of the nucleophile before it fully diffuses away into the solvent, thereby slightly favoring back-side attack (inversion). Answer: Statement I is false but S

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