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MHT CET202526 Apr 2025Morning ShiftChemistryHaloalkanes and HaloarenesActual

Identify the product when chlorobenzene is heated with nitrating mixture.

Options

  1. AOnly 1-chloro-4-nitrobenzene
  2. BOnly 1-chloro-2-nitrobenzene
  3. CMixture of 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene
  4. D2,4,6-trinitrochlorobenzene

Correct answer

C. Mixture of 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene

Step-by-step solution

Nitration of chlorobenzene proceeds via electrophilic aromatic substitution with the nitronium ion NO₂+ . The chloro substituent exhibits both inductive electron-withdrawing and mesomeric electron-donating effects, rendering it ortho-para directing while deactivating the ring. Attack occurs at both ortho and para positions relative to chlorine. This yields two isomeric products: 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene . The para isomer predominates due to reduced steric hindrance compared to the ortho p

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