---
title: "A student investigates the physical properties of three structural isomers with the molecular formula \\(\\text{C}_4\\text{H}_{10}\\text{O}\\). The structural formulas and molar masses of the compounds are shown in the table below.  | Compound | Structural formula | Molar mass (g/mol) | | :— | :— | :— | | X | \\(\\text{CH}_3\\text{CH}_2\\text{OCH}_2\\text{CH}_3\\) | 74.12 | | Y | \\((\\text{CH}_3)_3\\text{COH}\\) | 74.12 | | Z | \\(\\text{CH}_3\\text{CH}_2\\text{CH}_2\\text{CH}_2\\text{OH}\\) | 74.12 |  Which of the following correctly ranks the compounds in order of increasing normal boiling point, and provides the best explanation?"
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url: "https://nerd-notes.com/ubq/119543/"
date_modified: "2026-08-21T05:03:18+00:00"
---

# A student investigates the physical properties of three structural isomers with the molecular formula \(\text{C}_4\text{H}_{10}\text{O}\). The structural formulas and molar masses of the compounds are shown in the table below.

| Compound | Structural formula | Molar mass (g/mol) |
| :— | :— | :— |
| X | \(\text{CH}_3\text{CH}_2\text{OCH}_2\text{CH}_3\) | 74.12 |
| Y | \((\text{CH}_3)_3\text{COH}\) | 74.12 |
| Z | \(\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OH}\) | 74.12 |

Which of the following correctly ranks the compounds in order of increasing normal boiling point, and provides the best explanation?

A student investigates the physical properties of three structural isomers with the molecular formula \(\text{C}_4\text{H}_{10}\text{O}\). The structural formulas and molar masses of the compounds are shown in the table below.

| Compound | Structural formula | Molar mass (g/mol) |
| :--- | :--- | :--- |
| X | \(\text{CH}_3\text{CH}_2\text{OCH}_2\text{CH}_3\) | 74.12 |
| Y | \((\text{CH}_3)_3\text{COH}\) | 74.12 |
| Z | \(\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OH}\) | 74.12 |

Which of the following correctly ranks the compounds in order of increasing normal boiling point, and provides the best explanation?

- **A.** Compound \(Z < Y < X\), because Compound \(X\) contains a polar ether group that maximizes dipole-dipole attractions, whereas Compound \(Z\) exhibits weaker hydrogen bonding.
- **B.** Compound \(Z < X < Y\), because the compact, branched geometry of Compound \(Y\) concentrates electron density into a stronger net dipole than the extended chain of Compound \(Z\).
- **C.** Compound \(X < Z < Y\), because although both Compound \(Y\) and Compound \(Z\) form hydrogen bonds, the spherical shape of Compound \(Y\) allows for more efficient molecular packing and stronger London dispersion forces than the elongated chain of Compound \(Z\).
- **D.** Compound \(X < Y < Z\), because Compound \(X\) cannot form intermolecular hydrogen bonds, and the linear chain of Compound \(Z\) provides a larger surface area of contact for London dispersion forces than the branched structure of Compound \(Y\).

*The answer key and step-by-step explanation are available to logged-in users at https://nerd-notes.com/ubq/119543/*