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Aryl halides are less reactive towards n...

Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to

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Aryl halides are less reactive towards nucleophilic substitution reaction due to the following reasons
() In haloarenes the lone pair of electron on halogen are in resonance with benzene ring So, C-Clbond acquires partial double bond character which strengthen C-Cl bond Therefore, they are less reactive towords nucleophilic substitution reaction.

(i) In haloarenes, the carbon atom attached to halogen is `sp^(2)` hybridised. The `sp^(2)` hybridised carbon is more electronegative than `sp^(3)` hybridised carbon. This `sp^(2)`-hybridised carbon in haloarenes can hold the electron pair of C-X bond more tightly and make this C-CI bond shorter than C-Cl bond of haloalkanes
Since, it is difficult to break a shorter bond than a longer bond, therefore, haloarenes are less reactive than haloarenes
In haloarenes, the phenyl cation will not be stabilised by resonance therefore `S_(N)1` mechanism ruled out
(iv) Because of the repulsion between the nucleaphile and electron rich arenes, aryl halides are less reactive than alkyl halides
The reactivity of aryl halides can be increased by the presence of an electron withdrawing group `(-(NO_(2))` at ortho and para positions. However, no effect on reactivity of haloarenes is observed by the presence of electron withdrawing group at meta-position. Mechanism of the reaction is as depicted with `""^(-)OH` ion.


From the above resonance, it is very clear that electron density is rich at orto and para positions. So, presence of EWG will fascilitate nucleophilic at ortho and para positions not on meta position.
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Knowledge Check

  • Aryl halides are less reactie towards nucleophilic substitution reaction as compared to alkyl halides due to ________.

    A
    the formation of less stable carbonium ion
    B
    resonance stabilisation
    C
    longer carbon halogen bond
    D
    the inductive effect
  • Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alyl halides due to

    A
    The formation of less stable carbonium ion
    B
    Resonance stabilization
    C
    The inductive effect
    D
    `sp^(2)` hybridised carbon attached to the halogen
  • Aryl halide are less reactive towards nucleophilic substitution reaction as compared to alkyl halie due to

    A
    The formation of less stable carbonium ion
    B
    Resonance stabilization
    C
    Longer carbon halogen bond
    D
    `sp^(2)`-hybridized carbon attached to the halogen
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