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Question
Discuss the nature of C – X bond in the haloarenes.
Solution
Resonance effect: Because the C – X bond has the characteristics of a partial double bond, it is extremely difficult to break.
(i) The C – X bond in haloarenes is extremely less reactive to nucleophilic groups.
(ii) The C atom linked to the halogen is sp2 hybridised in the C – X bond. Carbon that has been sp2 hybridised with a higher s-character is more electronegative in nature and can retain the electron pair of the C – X bond more tightly than carbon that has been sp3 hybridised with a lower s-character in haloalkanes.
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