1‑Chloro‑2‑methylpropane is refluxed with excess aqueous $\mathrm{NaOH}$. Name the major organic product and briefly explain the mechanism.

Step-by-step solution

1. 1. Identify the substrate: 1‑chloro‑2‑methylpropane is a primary alkyl chloride.
2. 2. $\mathrm{NaOH}$ in aqueous medium is a strong nucleophile and base.
3. 3. Primary chlorides react with $\mathrm{NaOH}$ mainly by an “S${}_{\mathrm{N}}$(2)” substitution mechanism.
4. 4. The ${\mathrm{OH}}^{-}$ ion attacks the electrophilic carbon bearing the chloride, displacing ${\mathrm{Cl}}^{-}$ in a single concerted step.
5. 5. The resulting alkoxide ion immediately protonates with water to give the alcohol.
6. 6. Hence the major product is 2‑methylpropan‑1‑ol.

Concept tested: SN2 substitution of primary alkyl halides

Published 7 September 2026 · Last updated 16 September 2026 · How this solution was prepared and checked