Which member of each of the following pairs would you expect...

Which member of each of the following pairs would you expect to be more soluble in water? Briefly explain your choices.
a. butane or 2-butanol
b. 2-propanol or 2-pentanol
c. 2-butanol or 2,3-butanediol

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Key Concepts

Hydrogen Bonding

Hydrogen bonding refers to the attractive interaction between a hydrogen atom in a molecule containing a polar bond (such as O–H) and an electronegative atom with a lone pair (such as oxygen in water). Molecules capable of hydrogen bonding with water are generally more soluble since these interactions help integrate the solute into the solvent’s structure.

Polarity and Hydrophilic Functional Groups

Polarity in molecules arises from differences in electronegativity between atoms, which results in partial charges. Hydrophilic functional groups, like hydroxyl groups, are polar and can interact favorably with water molecules, enhancing solubility. The presence or absence of these groups is critical in determining whether a molecule will dissolve in water.

Effect of Alkyl Chain Length

The length of the alkyl chain in a molecule influences its solubility in water because longer nonpolar chains increase hydrophobic character. Even when a molecule contains polar groups, a sufficiently long nonpolar section can reduce overall solubility as the hydrophobic interactions tend to dominate over polar interactions with water.

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