JEE Main Chemistry question

[AIEEE 2012] *o*-Nitrophenol is less soluble in water than its *m*- and *p*-isomers because

(A)*o*-Nitrophenol shows intramolecular hydrogen bondingCorrect
(B)*o*-Nitrophenol shows intermolecular hydrogen bonding
(C)The melting point of *o*-nitrophenol is lower than those of the *m*- and *p*-isomers
(D)*o*-Nitrophenol is more volatile in steam than the *m*- and *p*-isomers

Answer: (A)

Solution

In *o*-nitrophenol the –OH and –NO₂ groups are close enough to form a strong intramolecular (chelated) hydrogen bond; this "uses up" the –OH's hydrogen-bonding capacity internally, leaving less

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Question ID VK-140394