The reaction of toluene with Cl _2 in presence of FeCl _3 gives 'X' and reaction in presence of light gives 'Y'. Thus, 'X' and 'Y' are:

NEET 2010 Chemistry question

The reaction of toluene with in presence of gives 'X' and reaction in presence of light gives 'Y'. Thus, 'X' and 'Y' are:

(1)X = Benzal chloride, Y = o-chlorotoluene
(2)X = m-chlorotoluene, Y = p-chlorotoluene
(3)X = o- and p-chlorotoluene, Y = Trichloromethyl benzeneCorrect
(4)X = Benzyl chloride, Y = m-chlorotoluene

Answer: (3)

Solution

With (a halogen carrier, no light) electrophilic substitution occurs on the ring. The group is an ortho/para director, so X is a mixture of o-chlorotoluene and p-chlorotoluene. In the presence of light (or heat) free-radical substitution occurs on the side chain:

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Question ID VK-090513