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Question

The chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH gives:

A
o–Cresol
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B
p–Cresol
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C
2,4–Dihydroxy toluene
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D
Benzyl alcohol
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Solution

The correct option is D Benzyl alcohol
Chlorination in the presence of heat and light proceeds through free radical mechanism. Since the free radical is stabilised more at the benzylic position, chlorination takes places preferentially at the benzylic position.

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