Out of chlorobenzene and benzyl chloride, which one gets easily hydrolysed by aqueous NaOH, and why?
Solution
Benzyl chloride (CHCHCl) hydrolyses readily: the CH–Cl bond breaks to give the resonance-stabilised benzyl carbocation (or undergoes easy S2), so aqueous NaOH converts it to benzyl alcohol.
In chlorobenzene the chlorine lone pairs are delocalised into the ring; the C–Cl bond acquires partial double-bond character and the carbon is sp — the bond is shorter, stronger and resistant to nucleophilic attack.
In chlorobenzene the chlorine lone pairs are delocalised into the ring; the C–Cl bond acquires partial double-bond character and the carbon is sp — the bond is shorter, stronger and resistant to nucleophilic attack.
CBSE Class 12 Board · 2018 · Subjective