Lecture29-notes

Lecture29-notes - 1 Epoxides A special group of ethers are...

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Unformatted text preview: 11/2/09 1 Epoxides A special group of ethers are epoxides. Here the oxygen is incorporated into a three- membered ring. We name epoxides commonly by using the name of the parent alkene followed by oxide. Epoxides Alternatively we can use the name of the parent alkane with an “epoxy” prefix Formation of epoxides can be accomplished by a reaction of a peracid with an alkene 11/2/09 2 Epoxides Reaction with hydrogen halides proceeds as with other ethers. Epoxides Reaction with water and alcohols can be accomplished via acid catalysis. 11/2/09 3 Epoxides For unsymmetrical epoxides we have to inspect the individual steps in the reaction more carefully. acidic conditions basic conditions We obtain different results depending on the reaction conditions used. Epoxides Acidic conditions: • First step is the formation of an oxonium species. • Attack of the nucleophile can take place at two positions. 11/2/09 4 Epoxides For the process of breaking the C-...
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Lecture29-notes - 1 Epoxides A special group of ethers are...

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