Question

Identify the product obtained when toluene reacts with chlorine in the presence of \(\text{FeCl}_{3}\).

• A. benzyl chloride
• B. m-Chloro toluene
• C. chlorobenzene
• D. o-Chlorotoluene and p-Chlorotoluene

Hint:

With a Lewis acid catalyst chlorination occurs on the ring, and the methyl group directs to the ortho and para positions.

Answer 1

The Correct Option is D

Step 1: Understanding the Concept
Chlorine with \(\text{FeCl}_{3}\) in the dark is electrophilic aromatic substitution on the ring, not on the side chain.

Step 2: Directing effect
The \(-\text{CH}_{3}\) group is electron donating through +I and hyperconjugation. It activates the ring and directs the incoming \(\text{Cl}^{+}\) to the ortho and para positions.

Step 3: Conclusion
The products are o-chlorotoluene and p-chlorotoluene. Benzyl chloride would form only by free-radical side-chain chlorination in sunlight or at high temperature.

Final Answer:
The products are o-chlorotoluene and p-chlorotoluene. \[ \boxed{\text{(D) }\text{o-Chlorotoluene and p-Chlorotoluene}} \]