Question

Why does not hydrogen-bonding occur in diethyl ether?

Answer 1

Because there are no hydrogens bound to a strongly electronegative element in diethyl ether.

Explanation:

Hydrogen bonding occurs where hydrogen is directly bound to a strongly electronegative element, typically oxygen or fluorine. In these circumstances, the electronegative element polarizes electron density towards itself to give bond polarity, which can significantly contribute to intermolecular bonding. The normal boiling points of both water, `100` `""^@C`, and hydrogen fluoride, `19.5` `""^@C`, are both anomalously high, and are the result of the extensive hydrogen bonding network between molecules.

By contrast, in diethyl ether, while the `C-O-C` link provides some polarity, hydrogen bonding does not occur as the `C-H` bond does not have any significant degree of bond polarity, of charge separation. The result? The normal boiling point of diethyl ether is relatively low at `34.6` `""^@C`.