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Explain as to why haloarenes are much less reactive than' haloalkanes towards nucleophilic substitution reactions?

Answer»

Solution :Haloarenes are much LESS reactive than haloalkanes towards nucleophilic substitution reactions due to the following reasons:
(i) RESONANCE effect: In haloarenes the electron pair on the halogen atom is in conjugation with the T-electrons of the ring and the following resonating structures are possible.

C-CI bond ACQUIRES a partial double bornd character due to resonance. As a result. the bond cleavage in haloarenes is difficult than in case of haloalkanesand therefore they are less reactive towards nucleophilic substitution reactions.
(ii) The C-Cl bond length in haloalkanes is 177 pm while in haloarenes it is 169 pm. Since it is difficult to break shorter bond than a longer bond. Therefore, haloarenes are less reactive than haloalkanes towards nucleophilic substitutión reactions.


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