Arrange these compounds in order of increasing boiling...

Arrange these compounds in order of increasing boiling point. Values in ${ }^{\circ} \mathrm{C}$ are $0,11,$ and 97 . (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$ (b) $\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}$ (c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Arrange these compounds in order of increasing boiling point. Values in ${ }^{\circ} \mathrm{C}$ are $0,11,$ and 97 .
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Key Concepts

Functional Groups

Functional groups are specific groups of atoms within molecules that dictate the molecules' chemical properties and reactivities. In the context of boiling point, different functional groups (like hydroxyl groups in alcohols, ether linkages in ethers, or alkyl groups in alkanes) influence the molecule's polarity and ability to form hydrogen bonds, which in turn affects their boiling points.

Molecular Polarity

Molecular polarity results from an unequal distribution of electron density, leading to permanent dipoles in a molecule. Polar molecules can engage in dipole-dipole interactions, which increase the energy required for the molecules to separate during boiling, thereby raising the boiling point.

Intermolecular Forces

Intermolecular forces are the attractions between individual molecules. These forces, which include hydrogen bonding, dipole-dipole interactions, and London dispersion forces, largely determine a substance's physical properties, such as its boiling point. Molecules with stronger intermolecular forces generally exhibit higher boiling points.

Hydrogen Bonding

Hydrogen bonding is a specific type of strong dipole-dipole interaction that occurs when a hydrogen atom bonded to a highly electronegative atom (such as oxygen) interacts with another electronegative atom in a neighboring molecule. This significantly enhances the boiling point compared to molecules that cannot hydrogen bond.

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