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  • Monochlorination of toluene in sunlight followed by hydrolysis with aq.{NaOH} yields. (i) o-Cresol (ii) m-Cresol (iii) 2, 4-Dihydroxytoluene (iv) Benzyl alcohol

Monochlorination of toluene in sunlight followed by hydrolysis with aq. \text {NaOH} yields.

(i) o-Cresol

(ii) m-Cresol

(iii) 2, 4-Dihydroxytoluene

(iv) Benzyl alcohol

Answers (1)

The answer is the option (iv). The monochlorination of toluene in sunlight results in halogenation that follows a free radical pathway and the product will react with the alkyl group forming haloalkyl.

And in the alkaline medium, the substitution reaction will take place resulting in the deduction of a hydrogen atom from the haloalkyl group. The end product formed will be alcohol; therefore, the monochlorination of toluene in light in the presence of aq. NaOH forms benzyl alcohol. So, option (iv) is the correct answer.

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