JEE Main Chemistry question

[IIT 2009] Among a chlorophenol (I), an isomeric chlorophenol (II), a chlorobenzoic acid (III) and a methylbenzoic (toluic) acid (IV), the correct order of decreasing acidity is

(A)III > IV > II > ICorrect
(B)IV > III > I > II
(C)III > II > I > IV
(D)II > IV > I > III

Answer: (A)

Solution

Carboxylic acids (pKa ≈ 4) are intrinsically far more acidic than phenols (pKa ≈ 10), even a chlorine-substituted one, so both benzoic-acid derivatives (III, IV) must rank ahead of both chlorophenols (I, II). Within the carboxylic-acid pair, the electron-withdrawing chloro

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Question ID VK-140203