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JEE Main Chemistry question

ChemistryAldehydes, Ketones and Carboxylic AcidsJEE Main

An aromatic compound X with molecular formula C₉H₁₀O gives the following chemical tests: (I) forms a 2,4-DNP derivative, (II) reduces Tollens' reagent, (III) undergoes Cannizzaro reaction, and (IV) on vigorous oxidation gives 1,2-benzenedicarboxylic acid. X is

Answer: (A)

Solution

X is an aldehyde (positive 2,4-DNP and Tollens') with no α-hydrogen on the carbonyl carbon (it undergoes Cannizzaro's reaction, so it must be an aromatic aldehyde, not an aliphatic one with α-H). Vigorous oxidation giving 1,2-benzenedicarboxylic (phthalic) acid means the ring bears a

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Question ID VK-149164