Question

Identify the product when chlorobenzene is heated with nitrating mixture.

• A. Only 1-chloro-4-nitrobenzene
• B. Only 1-chloro-2-nitrobenzene
• C. Mixture of 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene
• D. 2,4,6-trinitrochlorobenzene

Hint:

Halogens are uniquely paradoxical in organic chemistry: they are the ONLY functional groups that are Deactivating overall but still heavily Ortho/Para-directing!

Answer 1

The Correct Option is C

Step 1: Understanding the Concept:
Chlorine is an ortho/para directing group in electrophilic aromatic substitution because of its $+R$ effect, despite being deactivating due to its $-I$ effect.

Step 2: Formula Application:
$\text{Chlorobenzene} + \text{conc. } HNO_3/\text{conc. } H_2SO_4 \to \text{Nitration}$.

Step 3: Explanation:
The reaction produces a mixture of ortho and para substituted products. 1-chloro-4-nitrobenzene (para) is the major product due to less steric hindrance, while 1-chloro-2-nitrobenzene (ortho) is the minor product.

Step 4: Final Answer:
A mixture of 1-chloro-2-nitrobenzene and 1-chloro-4-nitrobenzene is formed.