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Question: Answered & Verified by Expert
Although chlorine is an electron withdrawing group, yet it is ortho-, para- directing in electrophilic aromatic substitution reactions. Why?
ChemistryHaloalkanes and HaloarenesNEET
Options:
  • A Chlorine donates electrons to the benzene ring, increasing electron density at the ortho and para positions.
  • B Chlorine's electron-withdrawing effect enhances the nucleophilic attack of the electrophile at the ortho and para positions.
  • C The inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends to oppose the inductive effect for the attack at ortho- and para positions and hence makes the deactivation less for ortho- and para- attack.
  • D Chlorine's electron-donating effect on the benzene ring makes it a meta-directing group in electrophilic aromatic substitution.
Solution:
2441 Upvotes Verified Answer
The correct answer is: The inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends to oppose the inductive effect for the attack at ortho- and para positions and hence makes the deactivation less for ortho- and para- attack.
Correct Option is : (C)
The inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends to oppose the inductive effect for the attack at ortho- and para positions and hence makes the deactivation less for ortho- and para- attack.

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