What is the major product formed when chlorobenzene is treated with methyl chloride in the presence of anhydrous (Friedel-Crafts alkylation)?
Answer and explanation
Correct answer: B. 1-Chloro-4-methylbenzene
- Step 1: In chlorobenzene, the chlorine atom has non-bonding lone pairs that direct incoming electrophiles to ortho and para positions through resonance stabilization.
- Step 2: Methylation introduces a methyl carbocation electrophile () onto the aromatic ring.
- Step 3: Due to steric hindrance at the ortho position, the para-isomer (1-chloro-4-methylbenzene) is obtained as the major product.
Answer
1-Chloro-4-methylbenzene (p-chlorotoluene).
Why not the others: m-Chlorotoluene is not formed because halogens are exclusively ortho/para directing; Toluene would require reductive removal of the chlorine atom; Benzyl chloride is a side-chain halogenated compound.
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