Question

What compounds can alkanes hydrogen bond with?

Answer 1

The simple answer is none, as alkanes do not engage in hydrogen bonding.

Explanation:

Hydrogen bonding is an intermolecular phenomenon, and occurs when hydrogen is bound to a strongly electronegative element, i.e. `F`, `O`, or `N`. In alkanes, the hydrogens are bound to carbon, and there is little difference between the electronegativity of hydrogen and carbon, and hence little bond polarity.

On the other hand, when hydrogen is bound to nitrogen or oxygen, the difference in electronegativity means that the heteroatom polarizes electron density towards itself, and polarity, charge separation can occur with respect to the bond. Such polarity gives rise to an additional intermolecular force that results in the in the elevated boiling points of water, alcohols, and amines.