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Explain why C – X bond in the haloarenes is extremely less reactive towards nucleophilic substitution than in haloalkanes.

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Reactions due to:

(i) Resonance effect: C – X bond acquires a partial double bond character and it becomes difficult to break C – X bond.

(ii) In C – X bond, C atom attached to halogen is sp2 hybridised. The sp2 hybridised carbon with a greater s character is more electronegative and can hold the electron pair of C – X bond more tightly than sp3 hybridised carbon in haloalkane with less 5- character. 

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