Which reaction will occur? o-cresol [ ] Conc. HCl ? vs o-cresol [ aq. NaOH ] -Cl ?

JEE Main Chemistry question

Which reaction will occur? -cresol ? vs -cresol ?

(A)Conc. HCl with heat causes no useful reaction on the phenolic ring (phenols resist electrophilic halogenation by HCl alone)
(B)Phenoxide displaces chloride from chlorobenzene (aryl-aryl ether formation, disfavoured since aryl halides resist nucleophilic substitution without activation)
(C)-Cresol's reacts with /aq. NaOH to O-methylate the ringCorrect
(D)None of these

Answer: (C)

Solution

Simple aqueous HCl (even with heat) cannot halogenate an unactivated phenol ring without a separate electrophilic halogen source, and aryl halides like chlorobenzene resist nucleophilic displacement by phenoxide under these mild conditions (no strong

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Question ID VK-148618