Discuss the nature of $C-X$ bond in the haloarenes.
CBSE DELHI - SET 3 2016
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In haloarenes, $C-X$ bond acquires a partial double bond character due to resonance.
As a result, the bond cleavage in haloarene is difficult than haloalkane and therefore, they are less reactive towards nucleophilic substitution reaction.
In haloalkane, the carbon atom attached to halogen is $sp^3$ hybridised while in case of haloarene, the carbon atom attached to halogen is $sp^2-$hybridised.
The $sp^2$ hybridised carbon with a greater $s-$character is more electronegative and can hold the electron pair of $C-X$ bond more tightly than $sp^3$ hybridised carbon in haloalkane with less $s-$character.
Thus, $C-Cl$ bond$-$length in haloalkane is $177 \ pm$ while in haloarene is $169 \ Pm.$
As a result, the bond cleavage in haloarene is difficult than haloalkane and therefore, they are less reactive towards nucleophilic substitution reaction.
In haloalkane, the carbon atom attached to halogen is $sp^3$ hybridised while in case of haloarene, the carbon atom attached to halogen is $sp^2-$hybridised.
The $sp^2$ hybridised carbon with a greater $s-$character is more electronegative and can hold the electron pair of $C-X$ bond more tightly than $sp^3$ hybridised carbon in haloalkane with less $s-$character.
Thus, $C-Cl$ bond$-$length in haloalkane is $177 \ pm$ while in haloarene is $169 \ Pm.$
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