---
title: "A student compares the relative solubilities of four alcohols in water, \\(\\text{H}_2\\text{O}\\), and hexane, \\(\\text{C}_6\\text{H}_{14}\\), at \\(25^\\circ\\text{C}\\). A small amount of each alcohol is added to a separate vial containing equal volumes of water and hexane. After each mixture reaches equilibrium, the student determines the ratio \\(R\\).  \\[ R=\\dfrac{[\\text{alcohol}]_{\\text{water}}}{[\\text{alcohol}]_{\\text{hexane}}} \\]  | Alcohol | Condensed structural formula | |———|——————————| | Methanol | \\(\\text{CH}_3\\text{OH}\\) | | Ethanol | \\(\\text{CH}_3\\text{CH}_2\\text{OH}\\) | | 1-Butanol | \\(\\text{CH}_3(\\text{CH}_2)_3\\text{OH}\\) | | 1-Hexanol | \\(\\text{CH}_3(\\text{CH}_2)_5\\text{OH}\\) |  Which choice correctly ranks the expected values of \\(R\\) from greatest to least?"
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url: "https://nerd-notes.com/ubq/119505/"
date_modified: "2026-08-19T12:40:51+00:00"
---

# A student compares the relative solubilities of four alcohols in water, \(\text{H}_2\text{O}\), and hexane, \(\text{C}_6\text{H}_{14}\), at \(25^\circ\text{C}\). A small amount of each alcohol is added to a separate vial containing equal volumes of water and hexane. After each mixture reaches equilibrium, the student determines the ratio \(R\).

\[
R=\dfrac{[\text{alcohol}]_{\text{water}}}{[\text{alcohol}]_{\text{hexane}}}
\]

| Alcohol | Condensed structural formula |
|———|——————————|
| Methanol | \(\text{CH}_3\text{OH}\) |
| Ethanol | \(\text{CH}_3\text{CH}_2\text{OH}\) |
| 1-Butanol | \(\text{CH}_3(\text{CH}_2)_3\text{OH}\) |
| 1-Hexanol | \(\text{CH}_3(\text{CH}_2)_5\text{OH}\) |

Which choice correctly ranks the expected values of \(R\) from greatest to least?

A student compares the relative solubilities of four alcohols in water, \(\text{H}_2\text{O}\), and hexane, \(\text{C}_6\text{H}_{14}\), at \(25^\circ\text{C}\). A small amount of each alcohol is added to a separate vial containing equal volumes of water and hexane. After each mixture reaches equilibrium, the student determines the ratio \(R\).

\[
R=\dfrac{[\text{alcohol}]_{\text{water}}}{[\text{alcohol}]_{\text{hexane}}}
\]

| Alcohol | Condensed structural formula |
|---------|------------------------------|
| Methanol | \(\text{CH}_3\text{OH}\) |
| Ethanol | \(\text{CH}_3\text{CH}_2\text{OH}\) |
| 1-Butanol | \(\text{CH}_3(\text{CH}_2)_3\text{OH}\) |
| 1-Hexanol | \(\text{CH}_3(\text{CH}_2)_5\text{OH}\) |

Which choice correctly ranks the expected values of \(R\) from greatest to least?

- **A.** \(\text{CH}_3(\text{CH}_2)_5\text{OH} > \text{CH}_3(\text{CH}_2)_3\text{OH} > \text{CH}_3\text{CH}_2\text{OH} > \text{CH}_3\text{OH}\), because the larger nonpolar portions strengthen dispersion forces with hexane, increasing \(R\).
- **B.** \(\text{CH}_3(\text{CH}_2)_5\text{OH} > \text{CH}_3(\text{CH}_2)_3\text{OH} > \text{CH}_3\text{CH}_2\text{OH} > \text{CH}_3\text{OH}\), because each additional \(\text{C-H}\) bond provides another site for hydrogen bonding with water.
- **C.** \(\text{CH}_3\text{OH} > \text{CH}_3\text{CH}_2\text{OH} > \text{CH}_3(\text{CH}_2)_3\text{OH} > \text{CH}_3(\text{CH}_2)_5\text{OH}\), because London dispersion forces between an alcohol and water become weaker as the carbon chain length increases.
- **D.** \(\text{CH}_3\text{OH} > \text{CH}_3\text{CH}_2\text{OH} > \text{CH}_3(\text{CH}_2)_3\text{OH} > \text{CH}_3(\text{CH}_2)_5\text{OH}\), because each molecule has one hydroxyl group, while increasing carbon-chain length increases affinity for nonpolar hexane relative to water.

*The answer key and step-by-step explanation are available to logged-in users at https://nerd-notes.com/ubq/119505/*