The bond length of C–Cl bond is larger in haloalkanes than that in haloarenes. Why?
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The C-Cl bond in haloarene is shorter than haloalkenes.
-In case of haloalkane,the carbon attached to halogen atom is sp³ hyhybridised where as in case of haloarenes,the carbon attached to the halogen atom is sp² hydridised.In sp²hybridisation,s character is 33% whereas in case of sp³ hybridisation,s character is 25%.We know higher is the s character higher will be the hybridisation is more electronegative & hence the bond pair of electron would be more closer to carbon,which results in the shortening of the C-Cl bond.
-In case of haloarenes,the lone pair of halogen atom participate in resonance with the benzene ring.This it is clearly visible for the above resonating structure that the C-Cl bond has 75% doble bond character&its bond order more than single bond &less than double bond.
-In case of haloalkane,the carbon attached to halogen atom is sp³ hyhybridised where as in case of haloarenes,the carbon attached to the halogen atom is sp² hydridised.In sp²hybridisation,s character is 33% whereas in case of sp³ hybridisation,s character is 25%.We know higher is the s character higher will be the hybridisation is more electronegative & hence the bond pair of electron would be more closer to carbon,which results in the shortening of the C-Cl bond.
-In case of haloarenes,the lone pair of halogen atom participate in resonance with the benzene ring.This it is clearly visible for the above resonating structure that the C-Cl bond has 75% doble bond character&its bond order more than single bond &less than double bond.
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Answer:
The lone pair of electron on chlorine atom undergoes resonance with benzene ring. Due to which, C-Cl bond acquires partial double bond character (169 pm) as compared to 170 pm haloalkane where C atom is hybridised.
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