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Why is ortho-nitrophenol less soluble in water than the meta- and para-nitrophenol isomers?

1. It is more volatile in steam than the meta and para isomers.
2. It forms intramolecular hydrogen bonding.
3. It forms intermolecular hydrogen bonding.
4. Its melting point is lower than that of the meta and para isomers.

Correct answer: It forms intramolecular hydrogen bonding.

Solution

Ortho-nitrophenol has a hydroxyl group and a nitro group positioned close together, allowing it to form intramolecular hydrogen bonds, which stabilizes the molecule and reduces its ability to interact with water, making it less soluble compared to the meta and para isomers.

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