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

<p><span data-teams="true">This is a multiple choice answer as classified in NCERT Exemplar</span></p><p> (IV) Benzyl alcohol</p><p>The chlorine atom is substituted by the hydrogen atom of&nbsp; methyl hydrocarbon present in toluene to form benzyl chloride on monochlorination of toluene in&nbsp; presence of sunlight by free radical pathway.</p><p>C₆H₅CH₃&nbsp; &nbsp; + &nbsp; Cl₂ &nbsp;<img src="https://images.shiksha.com/mediadata/images/articles/1746522802php4IBYQP.jpeg" alt="" width="82" height="40"> C₆H₅CH₂Cl</p><p>Toluene&nbsp; Benzyl Chloride</p><p>Benzyl chloride (monochlorinated toluene product) on hydrolysis with aq. NaOH yields benzyl alcohol by substituting the chloride ion by OH^- ion by nucleophilic substitution reaction.</p><p>C₆H₅CH₂Cl <img src="https://images.shiksha.com/mediadata/images/articles/1746522802php4IBYQP.jpeg" alt="" width="48" height="40"> C₆H₅CH₂OH</p><p>Benzyl&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Benzyl</p><p>Chloride&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Alcohol</p>

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