1‑Chloropropane ($\mathrm{C}{\mathrm{H}}_3\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{Cl}$) is refluxed with excess aqueous NaOH. Which compound is obtained as the major product?

Step-by-step solution

1. Identify the substrate: 1‑chloropropane is a primary alkyl halide.
2. In aqueous NaOH, the nucleophile is $\mathrm{O}{\mathrm{H}}^{-}$, a strong nucleophile.
3. Primary halides undergo bimolecular nucleophilic substitution (SN2) because steric hindrance is minimal.
4. In SN2 the nucleophile attacks the carbon bearing the leaving group from the backside, displacing $\mathrm{C}{\mathrm{l}}^{-}$.
5. The product of substitution is $\mathrm{C}{\mathrm{H}}_3\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{OH}$, i.e., propan-1-ol.

Concept tested: SN2 substitution of primary haloalkane

Published 15 September 2026 · How this solution was prepared and checked