Question

Why is chlorobenzene resistant to nucleophilic substitution reaction?

Hint:

The resonance effect in aromatic systems increases bond strength and decreases reactivity towards nucleophilic substitution.

Answer 1

Chlorobenzene is resistant to nucleophilic substitution due to the resonance stabilization of the C–Cl bond in the aromatic ring. The lone pair of electrons on the chlorine atom delocalizes into the benzene ring, making the carbon–chlorine bond stronger and less susceptible to attack by nucleophiles.