Arrange the compounds in Exercise 13.74 in order of...

Arrange the compounds in Exercise 13.74 in order of decreasing boiling point. Explain your answer.

$$
\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2-\mathrm{OH} \quad \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3 \quad \mathrm{CH}_3 \mathrm{CH}_2-\mathrm{O}-\mathrm{CH}_3
$$

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Key Concepts

Intermolecular Forces

Intermolecular forces are the attractions between molecules that impact their physical properties, such as boiling points. In a boiling point comparison, stronger intermolecular forces (like hydrogen bonding) require more energy to overcome, leading to higher boiling points.

Hydrogen Bonding

Hydrogen bonding is a particularly strong type of intermolecular force that occurs when a hydrogen atom covalently bonded to an electronegative atom such as oxygen interacts with another electronegative atom. Its presence in a molecule can significantly elevate the boiling point compared to similar compounds lacking this interaction.

Polarity

Polarity refers to the uneven distribution of electron density in a molecule, resulting in a positive end and a negative end. Polar molecules experience dipole-dipole interactions, which add to the overall intermolecular attractions and can lead to higher boiling points compared to nonpolar molecules.

Molecular Structure

Molecular structure, including aspects such as molecular size, shape, and the presence of functional groups, directly influences the types and strengths of intermolecular forces that operate. Structural differences can determine whether a molecule is capable of hydrogen bonding or mainly exhibits London dispersion forces, ultimately affecting its boiling point.

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