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Oxacyclopropanes, also known as epoxides (11)

Organic chemistry: Oxacyclopropanes, also known as epoxides, oxiranes, or ethylene oxides. Ring strain. Synthesis of oxacyclopropanes with peroxycarboxylic acids (peracids) such as peracetic acid or MCPBA. Acid-catalyzed ring opening; ring opening with anionic nucleophiles; ring opening with lithium aluminum hydride (LiAlH4). Diol (glycol) synthesis--anti dihydroxylation of an alkene via hydrolysis of oxacyclopropane intermediate; syn dihydroxylation of an alkene with osmium tetroxide (OsO4). Effect of a negative formal charge on reactivity. Regiochemistry of oxacyclopropane ring opening—when does the nucleophile attack the more substituted carbon and when does it attack the less substituted carbon? This is a recording of a tutoring session, posted with the students' permission. These videos are offered on a "pay-what-you-like" basis. You can pay for the use of the videos at my website: http://www.freelance-teacher.com/videos.htm For a list of all the available video series, arranged in suggested viewing order, go to my website. For a playlist containing all the videos in this series, click here: http://www.youtube.com/watch?v=bviuiAtWjFw&feature=PlayList&p=87E1D0647B1D8F7B&index=0&playnext=1 (1) Definition of oxacyclopropane. Ring strain. Peroxycarboxylic acids (peracids) such as peracetic acid and MCPBA (2) Peracids continued. Synthesis of oxacyclopropanes with peracids (3) Continued (4) Continued. Acid-catalyzed ring opening (5) Continued (6) Continued (7) Continued (8) Diol (glycol) synthesis--anti dihydroxylation of an alkene via hydrolysis of oxacyclopropane intermediate (9) Diol (glycol) synthesis--syn dihydroxylation of an alkene with osmium tetroxide (OsO4). Oxacyclopropane ring opening with anionic nucleophiles (10) Anionic nucleophiles continued. Effect of a negative formal charge on reactivity. Oxacyclopropane ring opening with lithium aluminum hydride (LiAlH4) (11) LiAlH4 continued. Regiochemistry of oxacyclopropane ring opening—when does the nucleophile attack the more substituted carbon and when does it attack the less substituted carbon? (12) Continued (13) Continued
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