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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3048

Which of the following statements about stereochemistry in the SN1 reaction of an optically active tertiary alkyl halide are correct?

  1. AComplete racemisation is expected only when the product-forming species is a free, symmetrically solvated planar cation.
  2. BProduct of retained configuration can arise from nucleophilic capture of the contact ion pair on the side from which the leaving group departed.
  3. CSubstrates that give more stable (longer-lived) carbocations show a higher degree of racemisation.
  4. DA tertiary substrate in a nucleophilic solvent always gives 100% inversion.

Answer: A, B, C

Statements 1-3 summarise the ion-pair picture: a free cation is attacked equally on both faces; a tight ion pair shields the departure face, so inversion predominates and retention arises from front-side capture; long-lived cations escape the ion pair and racemise. Statement 4 is false, since SN1 does not give complete inversion.
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