---
title: "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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url: "https://nerd-notes.com/ubq/123642/"
date_modified: "2026-09-28T12:01:53+00:00"
---

# 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?

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?

- **A.** Diethyl ether will elute first, because butan-1-ol forms stronger hydrogen bonds with the surface silanol groups of the stationary phase, causing it to be retained longer in the column.
- **B.** Diethyl ether will elute first, because its greater polarizability allows it to establish stronger London dispersion forces with the hexane mobile phase than butan-1-ol can.
- **C.** Butan-1-ol will elute first, because its hydroxyl group interacts more favorably through dipole-dipole attractions with the nonpolar hexane mobile phase than diethyl ether does.
- **D.** Butan-1-ol will elute first, because the two lone pairs on the ether oxygen in diethyl ether create stronger dipole-dipole attractions with the stationary phase than the single hydroxyl group in butan-1-ol.

*The answer key and step-by-step explanation are available to logged-in users at https://nerd-notes.com/ubq/123642/*