lec17_handout - 17 Massachusetts Institute of Technology...

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Unformatted text preview: 17 Massachusetts Institute of Technology Organic Chemistry 5.13 October 20, 2003 Prof. Timothy F. Jamison Notes for Lecture #17 Sigmatropic Rearrangments Woodward-Hoffmann Rules for Sigmatropic Rearrangments Stereochemical Course # Electrons Thermal Mode Photochemical Mode 4n + 2 [s,s] [s,a] 4n [s,a] [s,s] Continued on next page... Summary of Unit 3 Molecular Orbital Theory, Pericyclic Reactions A. Molecular Orbital Theory 1. Ethylene 2. Allyl cation, radical, anion 3. 1,3-Butadiene 4. Benzene 5. Cyclobutadiene – Frost’s Circle (Polygon Rule) B. Cycloaddition Reactions 1. Diels-Alder Reaction a. Basics – diene + dienophile (electron-poor) b. Only s-cis conformation of diene reacts. c. Cantharidin example d. Stereochemical course – part 1: Always suprafacial with respect to dienophile – stereospecific. e. Diels-Alder is a concerted reaction f. Frontier Molecular Orbital analysis of Diels-Alder reaction. HOMO of diene interacts with LUMO of dienophile. “HOMO/LUMO analysis”. g. Stereochemical course – part 2: Always suprafacial with respect to diene....
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lec17_handout - 17 Massachusetts Institute of Technology...

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