Epoxide
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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. Example: epoxyethane
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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