Question

Which one of the following halogen compounds is difficult to be hydrolysed by $S_{N}1$ mechanism?

• A. Tertiary butyl chloride
• B. Isopropyl chloride
• C. Benzyl chloride
• D. Chlorobenzene
• E. Allyl chloride

Answer 1

Answer: (D)

Chlorobenzene

$C-Cl$ bond in chloro benzene is stable due to delocalisation of electrons by resonance. Also, $(C-Cl)$ bond posses a double bond character due to which it is very difficult to hydrolyse it by $S_{N}1$ mechanism.