Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

The nitration of chlorobenzene gives major product as:

Options:

1-Chloro-2,4-nitrobenzene

1-Chloro-2-nitrobenzene

1-Chloro-4-nitrobenzene

1-Chloro-3-nitrobenzene

Correct Answer:

1-Chloro-4-nitrobenzene

Explanation:

The correct answer is Option (3) → 1-Chloro-4-nitrobenzene

Reason:

In chlorobenzene (C₆H₅Cl), the –Cl group is:

  • Ortho-para directing (due to +R effect of lone pair on chlorine)
  • Deactivating (due to –I effect and partial double bond character in C–Cl)

During electrophilic aromatic substitution (nitration), the incoming nitro (NO₂⁺) group prefers the para position over ortho because:

  • Para position faces less steric hindrance
  • Ortho position has steric repulsion between –Cl and incoming –NO₂
  • Although both ortho and para are activated relative to meta, para product dominates

Product distribution (typical):

  • para-nitrophenol: ~70–75% (major product)
  • ortho-nitrophenol: ~25–30%
  • meta: negligible (because –Cl is not meta-directing)

Thus, the major product of nitration of chlorobenzene is: 1-Chloro-4-nitrobenzene (p-nitrochlorobenzene)