3-hydroxybenzyl alcohol (resorcinol-type ring with -CH_2OH and -OH) is treated with (i) K_2CO_3 and (ii) CH_3I. The product A is

JEE Main Chemistry question

3-hydroxybenzyl alcohol (resorcinol-type ring with and ) is treated with (i) and (ii) . The product is

(A)The phenolic ring with ring methylated to , while the side-chain is left unchangedCorrect
(B)The side-chain methylated while ring is unchanged
(C)Both groups methylated
(D)Neither group methylated

Answer: (A)

Solution

is a mild base strong enough to deprotonate the more acidic phenolic (forming a phenoxide) but not the much less acidic, alcoholic side-chain ; the phenoxide then undergoes

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Question ID VK-148534