At 25 °C, three structural isomers of butanol are available: 1-butanol, 2-butanol,…
CHEMISTRY · Multi-part · AP · Chemistry · Properties of Substances and Mixtures · Properties of Substances and Mixtures
Problem
At 25 °C, three structural isomers of butanol are available: 1-butanol, 2-butanol, and tert-butanol. Each is placed in excess distilled water, and the mixtures are allowed to reach equilibrium with the undissolved liquid phase present.
(a) Rank the isomers from most soluble to least soluble in water.
(b) Provide a mechanistic explanation for the trend, citing specific intermolecular interactions between each isomer and water as well as any steric or entropic considerations that influence the extent of dissolution.