JEE Main · 2023 · 01 Feb 2023 · Shift 1 · Haloalkanes and Haloarenes

Aqueous potassium hydroxide favours nucleophilic substitution, so 1-bromopropane with $\mathrm{KOH}(\mathrm{aq})$ correctly gives propan-1-ol. Friedel-Crafts acylation of chlorobenzene with acetyl chloride and anhydrous $\mathrm{AlC}{\mathrm{l}}_3$ correctly gives chloroacetophenone, and chlorobenzene heated with sodium hydroxide at $623\mathrm{K}$ and $300\mathrm{atm}$ followed by acidification correctly gives phenol by the Dow process. The remaining change, neopentyl bromide with alcoholic KOH written to yield neopentyl alcohol, is wrong, because alcoholic KOH promotes elimination rather than substitution and the neopentyl framework in any case has no $\beta$-hydrogen and resists clean substitution. The incorrectly represented conversion is the neopentyl bromide reaction.