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When toluene is treated with Cl2 in the presence of Fe in dark, the product formed is

  • A.Benzyl chloride
  • B.mixture of o- & p-Chlorotoluene
  • C.2,4,6-Trichlorotoluene
  • D.2,4-Dichlorotoluene
  • E.Benzal dichloride

Answer: B

The product is a mixture of o- and p-chlorotoluene.

With a Lewis acid catalyst (Fe, which forms FeCl3) and in the dark, chlorine substitutes on the ring by electrophilic aromatic substitution. The methyl group is ortho-para directing, so 2-chlorotoluene and 4-chlorotoluene are formed.

Benzyl chloride and benzal dichloride are side-chain products, formed by free radical chlorination in sunlight or on heating without a catalyst. Di- and trichlorotoluenes need excess chlorine, not the simple monochlorination asked about.

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