QuestionOrganic / side-chain halogenation
The product formed by the reaction of toluene with chlorine in the presence of sunlight is:
- (a) o-chlorotoluene
- (b) 2,4-dichlorotoluene
- (c) p-chlorotoluene
- (d) benzylchloride
Answer: (d) benzylchloride
Cl₂ in sunlight (hν), no Lewis acid → free-radical substitution at the benzylic C–H → benzyl chloride C₆H₅CH₂Cl → (d). With FeCl₃ (dark) → o/p-chlorotoluene.