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Ch.13 - Solutions
Chapter 13, Problem 1

Examine the structures of phenol and naphthol shown here and explain why phenol is so much more soluble in water at 25 °C (87 g/L) compared to naphthol (0.74 g/L).

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1
<Phenol (C6H5OH) and naphthol (C10H7OH) are both aromatic compounds with a hydroxyl group (-OH) attached to their benzene rings.>
<The solubility of a compound in water is influenced by its ability to form hydrogen bonds with water molecules.>
<Phenol has a single benzene ring, which allows the hydroxyl group to interact more effectively with water, forming hydrogen bonds.>
<Naphthol, on the other hand, has two fused benzene rings, which makes the molecule bulkier and reduces the accessibility of the hydroxyl group to water molecules, thus limiting hydrogen bonding.>
<The increased hydrogen bonding capability of phenol compared to naphthol results in its higher solubility in water.>