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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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NCERT EXEMPLAR-HALOALKANES AND HALOARENES-Haloalkanes And Haloarenes
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  4. Match the structures of compounds given in Column I with the classes o...

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  5. Match the reactions given in Column I with the types of reactions give...

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  6. Match the structures given in Column I with the names in Column II

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  7. Match the reactions given in Column I with the names givn in Column II...

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  8. Assertion ( A) Phosphorus chlorides ( tri and penta) are preferred ove...

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  9. Assertion( A) The boiling points of alkyl halides decrease in the orde...

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  10. Assertion( A) KCN reacts with methyl chloride to give methyl isocyanid...

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  11. Assertion (A) tert-butyl bromide undergoes Wurtz reaction to give 2,2,...

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  12. Assertion (A) Presence of a nitro group at ortho or para position incr...

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  13. Assertion: In monohaloarenes, further electrophilic substitution occur...

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  14. Assertion: Aryl iodides can be prepared by reaction of arenes with iod...

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  15. Assertion: It is difficult to replace chlorine by -OH in chlorobenzene...

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  16. Assertion (A) Hydrolysis of (-)-2-bromooctane proceeds with inversion ...

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  17. Assertion (A) Nitration of chlorobenzene leads to the formation of m-n...

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  18. Some alkyl halides undergo substitutionn whereas some undergo eliminat...

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  19. Some halogen containing compounds are useful in daily life. Some compo...

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  20. Aryl halides are less reactive towards nucleophilic substitution react...

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