The reaction of toluene with $\mathrm{Cl}_{2}$ in presence of $\mathrm{FeCl}_{3}$ gives predominantly

JEE Main · 2007 · 29 Apr 2007 · Offline · Hydrocarbons

The reaction of toluene with

Cl_{2}

in presence of

FeCl_{3}

gives predominantly

(A)benzoyl chloride
(B)benzyl chloride
(C)o-and p-chlorotoluene✓ Correct
(D)m-chlorotoluene

Answer: (C)

Solution

In the presence of the Lewis acid

FeC l_{3}

the chlorine acts as an electrophile and attacks the aromatic ring rather than the side chain. The methyl group of toluene is an ortho, para-directing activator, so substitution takes place mainly at the positions ortho and para to it. The products that predominate are therefore o- and p-chlorotoluene.

JEE Main · 2007 · 29 Apr 2007 · Offline · Single correct option

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