Question

Why is chlorobenzene resistant to nucleophilic substitution reactions?

Hint:

The electron-withdrawing effect of the chlorine atom and the resonance stabilization in chlorobenzene make it resistant to nucleophilic substitution reactions, unlike alkyl halides where such substitution is easier.

Answer 1

Chlorobenzene is resistant to nucleophilic substitution due to the electron-withdrawing effect of the chlorine atom, which decreases the electron density on the benzene ring. This makes the carbon attached to the chlorine less electrophilic, which reduces its ability to undergo nucleophilic attack. Additionally, the resonance stabilization of the chlorine atom with the aromatic ring further makes the carbon-chlorine bond stronger, thus making nucleophilic substitution less favorable.