Which of the following correctly describes the relationship between hydrogen bonding and molecular solubility?

The correct understanding of the relationship between hydrogen bonding and molecular solubility lies in the principle of "like dissolves like." Substances that engage in hydrogen bonding typically interact well with other molecules that can also form hydrogen bonds. This strong interaction leads to enhanced solubility in polar solvents, particularly water.

When considering the role of hydrogen bonding, it is important to recognize that increased hydrogen bonding usually enhances solubility in solvents that can also form hydrogen bonds. For instance, compounds that can form hydrogen bonds with water—such as alcohols, acids, and amines—generally exhibit higher solubility in water.

If a substance exhibits strong hydrogen bonding but is mixed with a nonpolar solvent, the solubility of the substance will be hindered. In this context, the assertion that increased hydrogen bonding decreases solubility would apply when evaluating interactions with nonpolar solvents, where the lack of compatible interactions leads to poor solubility.

Thus, when analyzing solubility in a broader sense, the type of solvent and the corresponding intermolecular forces play a crucial role, and hydrogen bonding is a significant factor in the solubility of many substances in polar solvents.