Question

Identify the product obtained when toluene is brominated in the presence of iron in dark.

• A. Mixture of o-Bromotoluene and p-Bromotoluene
• B. o-Bromotoluene
• C. p-Bromotoluene
• D. Benzyl bromide

Hint:

With Fe in the dark, the reaction is electrophilic substitution on the ring, directed by the methyl group to ortho and para positions.

Answer 1

The Correct Option is A

Step 1: Understanding the Concept
Bromine with iron (a Lewis acid) in the dark brominates the benzene ring, not the side chain.

Step 2: Directing Effect
The methyl group is electron donating and activates the ring. It directs the incoming electrophile to the ortho and para positions.

Step 3: Products
Both o-bromotoluene and p-bromotoluene form, so the product is a mixture.

Step 4: Conclusion
Benzyl bromide forms only in light or at high temperature by a free radical route. The answer is option (A).

Final Answer:
The product is a mixture of o-bromotoluene and p-bromotoluene. \[ \boxed{\text{(A) }\text{Mixture of o-Bromotoluene and p-Bromotoluene}} \]