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Arylhalides are less reactive towards Nucleophilic substitution reactions than halo alkanes. Explain?

Arylhalides are less reactive towards Nucleophilic substitution reactions than halo alkanes. Explain?

Grade:12

1 Answers

vamshi
199 Points
8 years ago
Arylhalides are less reactive towards Nucleophilic substitution reactions than haloalkanes due
to the following reasons:
(i) Resonance Effect: In Arylhalides, the electron pairs on halogen atom are in conjugation
with π -electrons of the ring. It consists of the following resonating forms:
C-Cl bond acquires a partial double bond character due to resonance. So this bond cleavage is
difficult.
(ii) Hybridization of carbon atom in C-X bond: Carbon atom being sp2 hybridized has
greater s-character and more electro negativity in Aryl halides. While in haloalkanes C-atom
is sp3 hybridized and less electronegative. So C-X bond in Arylhalides is shorter and
stronger than it is in halo alkanes.
(iii) Instability of phenyl cation: In Arylhalides, the phenylcation is not stabilized by
resonance.
 

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