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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. NaOH yields. (i) o-Cresol (ii) m-Cresol (iii) 2, 4-Dihydroxytoluene (iv) Benzyl alcohol
Alcohols, Phenols, and Ethers | CBSE | Chemistry | Class 12 | ncert exemplar
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

Option (iv) is the answer.

Explanation:

In the presence of light, halogenation follows the free radical pathway, and therefore reacts with the alkyl group to produce halo alkyl.

In the presence of an alkaline media, the produced haloalkyl will undergo a substitution process, forming an alcohol by replacing the halogen atom in the haloalkyl group.

The toluene reaction can be represented as:

$\underset{\text { toluene }}{\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3} \stackrel{\mathrm{Cl}_{2}, \mathrm{hv}}{\rightarrow}} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl} \stackrel{\text { aq.NaOH }}{\rightarrow} \underset{\text { benzvl alcohol }}{\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}}$
benzyl alcohol

i

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