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Lecture 14 - Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis

Lecture 14 - Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis

This video was recorded at CHEM 125b: Freshman Organic Chemistry II. The formation of epoxides and the regiospecificity of their acid- and base-catalyzed ring openings underlines the importance of thinking carefully about how textbooks draw curved arrows and may sometimes read too much into fundamentally inadequate experimental data. The ozonolysis of alkenes begins with several 1,3-dipolar cycloadditions that can be understood in terms of matching HOMOs with LUMOs of the corresponding symmetry. The process continues with acetal hydrolysis and either reduction or oxidation to obtain the desired product. Mechanisms of these typical reactions are analyzed. Although addition to the C=O double bond is usually considered nucleophilic, it can have an important electrophilic component that makes... Show More
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