AP Chemistry
3.9 Separation of Solutions and Mixtures
3.1 Intermolecular and Interparticle Forces
A student uses liquid column chromatography to separate an equimolar mixture of two constitutional isomers: diethyl ether (\(\text{CH}_3\text{CH}_2\text{OCH}_2\text{CH}_3\), molar mass \(74.12 \text{ g/mol}\)) and butan-1-ol (\(\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OH}\), molar mass \(74.12 \text{ g/mol}\)). The column is packed with silica gel, a polar stationary phase with abundant surface silanol groups (\(\text{–Si–OH}\)), and the mobile phase is nonpolar hexane (\(\text{C}_6\text{H}_{14}\)). Based on the structural features and relative intermolecular attractions of the compounds, which compound will elute from the column first, and what is the correct justification?
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