JEE Main Chemistry question

Between *p*-nitrophenol and salicylaldehyde, solubility in aqueous base is

(A)Almost nil in both cases
(B)Higher in *p*-nitrophenolCorrect
(C)Higher for salicylaldehyde
(D)Equal in nature

Answer: (B)

Solution

*p*-Nitrophenol's phenolic –OH is strongly acidified by the *para* –NO₂ group (pKₐ ≈ 7.2), so it deprotonates and dissolves readily in base. Salicylaldehyde's *ortho* –OH and –CHO form

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Question ID VK-140357