Why does not hydrogen-bonding occur in diethyl ether?

Question

Ellie Andrews · Accepted Answer

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

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#.

Wyatt Adkins · Answer

undefined Hydrogen bonding does not occur in diethyl ether because it lacks hydrogen atoms bonded to highly electronegative atoms such as nitrogen, oxygen, or fluorine, which are necessary for hydrogen bonding to occur.

Jeremiah Adams · Answer

undefined Hydrogen bonding requires a hydrogen atom bonded directly to a highly electronegative atom (such as oxygen, nitrogen, or fluorine) to interact with a lone pair of electrons on another highly electronegative atom. In diethyl ether (CH3CH2OCH2CH3), there are no hydrogen atoms bonded directly to highly electronegative atoms. The hydrogen atoms in diethyl ether are bonded to carbon atoms, which are less electronegative than oxygen, so they do not create the necessary conditions for hydrogen bonding to occur. Therefore, diethyl ether does not exhibit hydrogen bonding.