Q.Explain only reaction mechanism for alkaline hydrolysis of tert-butylbromide.
You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.
Start your 14-day free trial to unlock the full solution →A tertiary halide ionises first (rate-determining step, stabilised carbocation), then the nucleophile attacks the planar cation in a fast second step.
tert-Butyl bromide, , being a tertiary alkyl halide, undergoes alkaline hydrolysis by the (substitution, nucleophilic, unimolecular) mechanism, in two steps:
Step 1 (slow, rate-determining): the polarised C–Br bond breaks heterolytically without any assistance from the incoming nucleophile, generating a planar tertiary carbocation (stabilised by hyperconjugation and the electron-donating inductive effect of the three methyl groups) and a bromide ion:
Step 2 (fast): the hydroxide ion, a strong nucleophile, rapidly attacks the planar, electrophilic carbocation (from either face, since it's planar/sp² at the reacting carbon), giving the alcohol product:
…
Unlock everything free for 14 days
- Full step-by-step solutions
- Concept-first explanations
- Methods, shortcuts & mistakes
- PYQ mapping + timed mock tests
Full access for 14 days. No credit card required.