MHT CET202526 Apr 2025Morning ShiftChemistryHaloalkanes and HaloarenesActual
Identify the product when chlorobenzene is heated with nitrating mixture.
Options
- AOnly 1-chloro-4-nitrobenzene
- BOnly 1-chloro-2-nitrobenzene
- CMixture of 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene
- 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