Lecture 14 - Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: February 2011,   views: 1590
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)
Categories

See Also:

Download Video - generic video source Download yalespan125bs2011_mcbride_lec14_01.mp4 (Video - generic video source 579.1 MB)

Download Video Download yalespan125bs2011_mcbride_lec14_01_640x360_h264.mp4 (Video 148.5 MB)

Download subtitles Download subtitles: TT/XML, RT, SRT


Help icon Streaming Video Help

Related Open Educational Resources

Related content

Report a problem or upload files

If you have found a problem with this lecture or would like to send us extra material, articles, exercises, etc., please use our ticket system to describe your request and upload the data.
Enter your e-mail into the 'Cc' field, and we will keep you updated with your request's status.
Lecture popularity: You need to login to cast your vote.
  Bibliography

Description

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 it mechanistically analogous to the "electrophilic" additions to C=C being discussed in these lectures. The use of metals to access orbitals of the proper symmetry is introduced through alkene dihydroxylation via cycloaddition of OsO4.

Link this page

Would you like to put a link to this lecture on your homepage?
Go ahead! Copy the HTML snippet !

Write your own review or comment:

make sure you have javascript enabled or clear this field: