JEE Main Chemistry question

Which of the following (each bearing an *ortho*-methyl group alongside the stated second substituent) is most reactive towards electrophilic reagents?

(A)*o*-Cresol (–OH, –CH₃)Correct
(B)2-Methylbenzyl alcohol (–CH₂OH, –CH₃)
(C)*o*-Acetamidotoluene (–NHCOCH₃, –CH₃)
(D)*o*-Methylanisole (–OCH₃, –CH₃)

Answer: (A)

Solution

Among –OH, –CH₂OH, –NHCOCH₃ and –OCH₃, the free phenolic –OH is the strongest ring-activating group (best lone-pair resonance donation, with no competing

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Question ID VK-140109