unit_3_study - Massachusetts Institute of Technology...

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Massachusetts Institute of Technology Organic Chemistry 5.13 October 11, 2006 Prof. Timothy F. Jamison Assignment and Study Guide for Unit III Molecular Orbital Theory, Pericyclic Reactions, and the Woodward-Hoffmann Rules O Me OH O Me H H Me H Me O O Me OH Me H H H Me H H Me H O O H Me OH H H absinthin 2 [4+2] Cycloaddition Diels-Alder Reaction Absinthin is a natural product that is isolated from wormwood. Extraordinarily bitter, it is the chief bitter component of absinthe , an intoxicating beverage that was quite popular in France in the late 19th century, especially in the artist community of that period, e.g. van Gogh and Toulouse-Lautrec. It is quite possible that the final step in the biosynthesis of absinthin involves a Diels-Alder cycloaddition reaction of two identical cyclopentadiene-containing molecules, as shown in the reaction above. Molecule of the Day absinthin Reading Assignments McMurry, Chapter 14 (pp. 464-497) (Also review McMurry, Chapter 15, pp. 498-527) Recommended Problems: Chapter 14:
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