Which of the following compounds would be expected to form...

Which of the following compounds would be expected to form intermolecular hydrogen bonds in the liquid state? (a) $\mathrm{CH}_{3} \mathrm{OCH}_{3}$ (dimethyl ether) (b) $\mathrm{CH}_{4}$ (c) HF (d) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ (acetic acid) (e) $\mathrm{Br}_{2}$ (f) $\mathrm{CH}_{3} \mathrm{OH}$ (methanol)

Which of the following compounds would be expected to form intermolecular hydrogen bonds in the liquid state?
(a) $\mathrm{CH}_{3} \mathrm{OCH}_{3}$ (dimethyl ether)
(b) $\mathrm{CH}_{4}$
(c) HF
(d) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ (acetic acid)
(e) $\mathrm{Br}_{2}$
(f) $\mathrm{CH}_{3} \mathrm{OH}$ (methanol)

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Key Concepts

Hydrogen Bonding

Hydrogen bonding is a type of intermolecular force that occurs when a hydrogen atom is covalently bonded to a highly electronegative atom such as oxygen, nitrogen, or fluorine, making the hydrogen partially positive and capable of interacting with a lone pair on another electronegative atom in a neighboring molecule.

Electronegativity and Bond Polarity

Electronegativity differences between atoms in a molecule create polar bonds, which are essential for hydrogen bonding. When hydrogen is bonded to an electronegative atom, the resulting bond polarity facilitates the attraction between that hydrogen and the lone pairs of electronegative atoms in nearby molecules.

Hydrogen Bond Donors and Acceptors

For hydrogen bonding to occur, a molecule must have a hydrogen bond donor (a hydrogen atom attached to an electronegative atom) and a hydrogen bond acceptor (a lone pair on an electronegative atom). Molecules that have these characteristics can form intermolecular hydrogen bonds, which significantly affect their physical properties.

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