epoxide

An epoxide is an ether in which the oxygen atom is part of a ring of three or more atoms. This ring is approximately an equilateral triangle, i.e. its bond angles are about 60°, which puts it under strain. The strained ring makes epoxides more reactive than other ethers. A polymer made of epoxide units is called a polyepoxide or an epoxy. Epoxy resins are used as adhesives and structural materials.

Reactions

Synthesis

alkene + percarboxylic acid → epoxide + carboxylic acid

Hydrolysis

epoxide + acid catalyst → trans glycol

Nucleophilic addition

epoxide + nucleophile → open epoxide ring

Reduction

#epoxide + lithium aluminum hydride + water → alcohol

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