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ortho-Nitrophenol is less soluble in water than p- and m-nitrophenols because:

1. o-Nitrophenol is more volatile steam than those of m- and p-isomers.
2. o-Nitrophenol shows intramolecular H-bonding
3. o-Nitrophenol shows intermolecular H-bonding
4. Melting point of o-nitrophenol is lower than those of m- and p-isomers.

Correct answer: o-Nitrophenol shows intramolecular H-bonding

Solution

In o-nitrophenol the OH and NO2 groups are adjacent and form an intramolecular hydrogen bond (chelation), so the molecule cannot hydrogen-bond effectively with water and is less soluble than the m- and p-isomers.

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