Ethers
Compounds with an oxygen bonded to two carbons, relatively unreactive solvents.
Compounds with an oxygen bonded to two carbons, relatively unreactive solvents.
Ethers have the general formula R-O-R', with an oxygen atom bonded to two carbon groups, and the C-O-C angle is bent, similar to water. Because they lack an O-H bond, ethers cannot form hydrogen bonds with each other, so they have lower boiling points than alcohols of similar mass. They are poorly reactive and are widely used as aprotic solvents, although they form explosive peroxides on storage when exposed to air. Ethers are cleaved by strong acids such as HI, which breaks the C-O bond.
Key ideas: General formula R-O-R, with a bent C-O-C angle of about 110 degrees; no O-H, so no hydrogen bonding and boiling points close to alkanes (diethyl ether 35 C). Fairly unreactive, used as solvents; cleaved by concentrated HI or HBr. They form explosive peroxides with air over time. IUPAC naming: alkoxyalkane (methoxyethane).
Common mistakes and connections: Students think ethers boil as high as alcohols, or forget the peroxide hazard. Another error is predicting cleavage products wrongly: with an aryl alkyl ether and HI the products are phenol and alkyl iodide, because aryl iodide does not form. Links to functional isomerism with alcohols and Williamson synthesis.
Diethyl ether boils at 308 K, like pentane, and far below isomeric 1-butanol (390 K), because ethers cannot hydrogen bond to themselves. The interactive lesson shows this as a live animation or chart.
Diethyl ether was once used as a general anaesthetic because it is volatile and relatively unreactive.
Compounds with an oxygen bonded to two carbons, relatively unreactive solvents.
Ethers is a intermediate topic in Organic Chemistry. It builds on the vocabulary of beginner topics in this area.
Study these earlier topics in Organic Chemistry first: Lucas Test, Ethanol Production, Phenols.
The next topics in Organic Chemistry are Williamson Ether Synthesis and Aldehydes.
Yes. The interactive lesson includes a self-check question on Ethers, and the Organic Chemistry quiz draws on every topic in this area.
Ethers is topic 70 of 148 in Organic Chemistry.