Why do electrophilic substitution reaction occur slowly in haloarenes?
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- Haloarenes have sp2 hybridized carbon atoms bonded to the halogen atoms, which have more s-character and hence, are more difficult to break than bonds formed by haloalkanes' carbon atoms with halogen atoms.
- Haloarenes have partial double-bond character in their carbon-halogen bond, due to resonance of the lone-pairs present on the halogen atoms.
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Also, the halogen atom has -I effect because it is a electron withdrawing group. As a result, it tends to deactivate the benzene ring. Therefore, the electrophilic substitution reactions of chlorobenzene occur slowly and under drastic conditions compared to benzene.
VedaantArya:
I would argue though, that the benzene ring as compared to an aliphatic substrate has higher electron density. A deactivating group may reduce it, but probably not enough to make haloarenes less reactive than haloalkanes.
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