Question

What is the product obtained on the reaction of chlorobenzene with concentrated HNO3?

• A. Para nitro chloro benzene
• B. Ortho nitro chloro benzene
• C. Mixture of ortho and para nitro benzene
• D.

Hint:

When working with aromatic substitution reactions, remember that the position of substitution is influenced by the nature of the substituent on the ring. Chlorine, being an electron-donating group, directs substitution to the ortho and para positions.

Answer 1

The Correct Option is C

Nitration of chlorobenzene with concentrated nitric acid proceeds via electrophilic aromatic substitution. The nitronium ion (\( \text{NO}_2^+ \)), generated from nitric acid, functions as the electrophile. The chlorine atom, via resonance, donates electron density to the benzene ring, activating it for substitution. This electron-donating effect directs the nitronium ion to attack predominantly at the ortho and para positions relative to the chlorine atom. Consequently, the reaction yields a mixture of ortho and para nitro chlorobenzene.
Step 1: Reaction mechanism- The benzene ring is attacked by the nitronium ion (\( \text{NO}_2^+ \)).- The chlorine group's electron-donating resonance effect directs this attack to the ortho and para positions relative to itself.
Step 2: ConclusionReaction of chlorobenzene with concentrated nitric acid produces a mixture of ortho and para nitro chlorobenzene. Therefore, the correct answer is \( \boxed{\text{Mixture of ortho and para nitro benzene}} \).