Organic Chemistry 5.13, Notes for Lectures #13 and 14 | Massachusetts Institute of Technology - Edubirdie

University:
Massachusetts Institute of Technology
Course:
5.13 | Organic Chemistry II
Academic year:

2020
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224

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1
Author:

Scarlett Grimes

13 Massachusetts Institute of Technology 14 Organic Chemistry 5.13 October 11 and 13, 2006 Prof. Timothy F. Jamison Notes for Lectures 13 and 14 Electrocyclic Reactions Molecule of the Day vitamin D (biosynthesis) H H H h! H HO H HO 7-dehydrocholesterol Definition: previtamin D3 A pericyclic reaction in which 1 conjugated, overlapping array of orbitals combines. Electrocyclic reactions proceed by way of a cyclic transition state, and 1 sigma bond is formed during the course of the reaction. Conrotatory: Orbitals rotate in the same direction (both clockwise or both counter-clockwise) Disrotatory: Orbitals rotate in opposite directions (one clockwise, one counter-clockwise) Woodward-Hoffmann Rules for Electrocyclic Reactions Stereochemical Course # Electrons Thermal Mode Photochemical Mode 4n + 2 disrotatory conrotatory 4n conrotatory disrotatory

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