MDCAT Chemistry MCQ #620

When (S)-2-bromobutane undergoes a strictly SN2 reaction with a cyanide ion, what is the specific stereochemical outcome observed in the product?

MDCAT Chemistry MCQ #620

  1. Question 1

    Q1. When (S)-2-bromobutane undergoes a strictly SN2 reaction with a cyanide ion, what is the specific stereochemical outcome observed in the product?

    • A) Complete retention of the original molecular configuration.
    • B) A 50/50 mixture of two different enantiomeric forms.
    • C) Partial racemization with slight excess of retention.
    • D) Complete inversion of the original molecular configuration.

    Answer: Complete inversion of the original molecular configuration.

    Explanation: SN1 involves a planar carbocation intermediate leading to racemization, while SN2 involves back-side attack causing 100% inversion of configuration.