Definitions

epoxide

epoxide

[e-pok-sahyd, ih-pok-]

An epoxide is a cyclic ether containing an oxygen atom attached to two adjacent carbon atoms of a hydrocarbon. Epoxides have greater reactivity than typical ethers. An example is ethylene oxide that acts as a fumigant and makes antifreeze. Industrial epoxides involve converting an alkene to a chlorohydrin, then treating the chlorohydrin with a base to get rid of hydrochloric acid. Acid or base conditions allow epoxides to form a variety of products such as propylene glycol. Epoxides can also assemble polymers such as epoxies, used as powerful adhesives. Epoxy resin comes from the reaction of epichlorohydrin with bisphenol A.

Ring strain causes epoxides' ease of reactivity. When nucleophiles attack the electrophilic carbon atom of the C-O bond, the bond breaks, the ring opens and relieves the ring strain. As a result, 2 alcohols get produced.

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