1‑Bromoisobutane (tert‑butyl bromide, $(C H_{3})_{3} C B r$ ) is refluxed with excess aqueous NaOH. Write the major organic product formed and explain the type of mechanism involved.

easy 1 mark Class 12 · Chemistry · Haloalkanes and Haloarenes

Answer

tert‑Butanol,

(C H_{3})_{3} C O H

The correct answer is tert‑Butanol, $(C H_{3})_{3} C O H$ — Deprotonation of the attached water gives the neutral alcohol $(C H_{3})_{3} C O H$ , which is the major product.

Step-by-step solution

The substrate is a tertiary haloalkane, so nucleophilic substitution proceeds by the SN1 mechanism.
In SN1, the C–Br bond breaks first to give a tertiary carbocation $(C H_{3})_{3} C^{+}$ and Br⁻.
Water (or OH⁻ from NaOH) then attacks the carbocation, forming $(C H_{3})_{3} C - O H$ .
Deprotonation of the attached water gives the neutral alcohol $(C H_{3})_{3} C O H$ , which is the major product.

Common mistake: Assuming an SN2 pathway for a tertiary substrate

Concept tested: SN1 hydrolysis of tertiary haloalkane

Published 16 September 2026 · How this solution was prepared and checked

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1‑Bromoisobutane (tert‑butyl bromide, (CH3​)3​CBr) is refluxed with excess aqueous NaOH. Write the major organic product formed and explain the type of mechanism involved.

Step-by-step solution

1‑Bromoisobutane (tert‑butyl bromide, $(C H_{3})_{3} C B r$ ) is refluxed with excess aqueous NaOH. Write the major organic product formed and explain the type of mechanism involved.