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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).

Verified step by step guidance
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.