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NEET levelSingle correct optionDifficulty 1 of 3hx147

Chlorobenzene is far less reactive than ethyl chloride towards nucleophilic substitution mainly because

Athe $C - Cl$ bond in chlorobenzene has partial double-bond character due to resonance and involves an $s p^{2}$ carbon
Bchlorine is absent in the ring
Cthe benzene ring has no pi electrons
Dthe $C - Cl$ bond in chlorobenzene is longer than in ethyl chloride

Answer: A

In chlorobenzene the lone pair of

Cl

delocalises into the ring, and carbon is

s p^{2}

hybridised. The

C - Cl

bond is therefore shorter and stronger than in ethyl chloride, and the phenyl cation that would form in

S_{N} 1

is unstable, so substitution is difficult.

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