MDCAT Chemistry MCQ #627

Comparing the hydrolysis of methyl bromide and tert-butyl bromide in aqueous medium, which mechanism is preferred by the tertiary halide and why?

MDCAT Chemistry MCQ #627

  1. Question 1

    Q1. Comparing the hydrolysis of methyl bromide and tert-butyl bromide in aqueous medium, which mechanism is preferred by the tertiary halide and why?

    • A) Methyl bromide reacts via SN1 because of high methyl stability.
    • B) Tert-butyl bromide reacts via SN2 due to low steric hindrance.
    • C) Tert-butyl bromide reacts via SN1 due to stable carbocation formation.
    • D) Methyl bromide reacts via E1 because it lacks beta-hydrogens.

    Answer: Tert-butyl bromide reacts via SN1 due to stable carbocation formation.

    Explanation: Tertiary alkyl halides favor SN1/E1 because the carbocation is stable, while primary halides favor SN2/E2 due to lack of steric hindrance.