Skip to content
qorganica.es qorganica.comOrganic Chemistry made transparent Course map Español

Physical and Bond Properties

Structurally speaking, ethers can be considered as derived from water or alcohols, in which two or one hydrogens, respectively, have been replaced by carbon chains.

Geometry of water: angle of 104.5° and boiling point of 100 °CGeometry of methanol: angle of 108.9° and boiling point of 65 °CGeometry of dimethyl ether: angle of 111.7° and boiling point of −25 °C
WaterMethanolDimethyl ether
Hydrogen-bond association decreases from water to methanol and does not exist in the ether

The angular structure of ethers is well explained by assuming that the oxygen is sp3 hybridized and bears two electron lone pairs. Ethers cannot establish hydrogen bonding and hence, they display much lower boiling and melting points than comparable alcohols.

A very special and important case is that of the epoxides (oxiranes), the three-membered cyclic ethers.

The ring is highly strained, similarly to cyclopropane.

The strain and the oxygen make it very reactive.

Molecular model of ethylene oxide
Ethylene oxide
Geometry of cyclopropane: C–C–C angle of 60°, C–C bonds of 1.50 Å and C–H bonds of 1.10 Å, H–C–H angle of 115° and eclipsed hydrogens
Geometry of ethylene oxide: C–C bond of 1.48 Å, C–O bond of 1.44 Å and an angle of 62.2° in the three-membered ring