8.7 Expoxidation, Anti-Dihydroxylation, and Syn-Dihydroxylation of Alkenes | Organic Chemistry

Chad covers three related alkene reactions in this lesson: Epoxidation, Anti-Dihydroxylation, and Syn-Dihydroxylation.  Chad begins by showing how a peroxyacid (such as MCPBA) can be used to convert an alkene to an epoxide including the epoxidation mechanism.  He then shows how subsequent treatment of the epoxide with hydronium opens the epoxide (acid-catalyzed ring opening of an epoxide) with a net result of anti-dihydroxylation including the mechanism.  Chad finally contrasts this with syn-dihydroxylation using either potassium permanganate (KMnO4) or osmium tetroxide (OsO4) both of which go through cyclic metal ester intermediates.

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00:00 Lesson Introduction
00:46 Epoxidation of Alkenes
02:36 Anti-Dihydroxylation of Alkenes
03:32 Epoxidation Mechanism
04:29 Anti-Dihydroxylation Mechanism
06:41 Syn-Dihydroxylation of Alkenes

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