CHEM 742

CHEM 742 – Physical Organic Chemistry II

Welcome to physical organic chemistry II. In this course we will discuss the chemistry of reactive intermediates such as free radicals and carbenes. We will cover Hückel molecular orbital theory and quantum chemistry as it pertains to organic reactions and mechanism. We will go in depth into the Woodward-Hoffmann rules for electrocyclic and pericyclic reactions. We will discuss aromaticity and electrophilic substitution. The goal of the course is to provide you with a mastery of mechanistic tools and principles to allow you to understand and predict the course of organic reactions.

Syllabus

Term Paper

Class Notes

Radical Chemistry
Carbenes Chemistry
Pericyclic Reactions and MO Theory
Diels Alder Cycloaddition
Aromaticity and Reactions of Aromatics
Intermolecular Forces

Useful information from around the internets

Radical Chemistry

Radicals: Fundamentals & Applications (Paulo Vital, Evans Group Presentation)
Radicals II: Stereoselective Reactions (Simone Bonazzi, Evans Group Presentation)
Timeless Methods for Radical Cyclization in Total Synthesis (Patricia Zhang, MacMillan Group Presentation)
Enantioselective Free Radical Reactions (Michael Ober, Denmark Group Presentation)
Ketyl Radical Anion in Samarium Iodide (SmI2) Chemistry (Hyung Min Chi, Denmark Group Presentation)
Use of Cp2TiCl in Synthesis (Jeff Kallemeyn, Denmark Group Presentation)

Carbene Chemistry

Chiral N-Heterocyclic Carbene Ligands in Asymmetric Catalysis (Peter Yao, Denmark Group Presentation)
N-Heterocyclic Carbenes: Versatile Organocatalysts and Reagents (Eugene Kwan, Evans Group Presentation)
Nucleophilic Heterocyclic Carbene Catalysis (Nathan Werner, Denmark Group Presentation)
Carbene Mediated C-H Activation (Joseph Carpenter, MacMillan Group)
Recent Developments in Rhodium Carbene and Nitrene Chemistry (Brian Ngo Laforteza, MacMillan Group)

Pericyclic Reactions

Pericyclic Reactions (McGraw-Hill textbook section)
Pericyclic Reactions (CHEM 212, Prof. Blake Peterson, Penn State)
Stereochemistry of Electrocyclic Reactions (Woodward and Hoffmann, JACS 1965, 87, 395)
Woodward-Hoffmann Rules Wikipedia
Woodward-Hoffmann Rules (CHM 242b, Scott Virgil, Cal Tech)
Conservation of Orbital Symmetry (Rob Knowles, MacMillan Group_
MO Description of Diels-Alder Cycloaddition (Youtube, Kevin Shea, Smith College)
Basic MO Theory (Chemogenesis)

Aromatic Chemistry

Electrophilic Aromatic Substitution (Chem 2600, U Lethbridge, Canada)
Short Course in Heterocyclic Chemistry Aromaticity and Tautomerizm (Prof. Alan Katrizky, U. Florida)
Short Course in Heterocyclic Chemistry Electrophilic Substitution (Prof. Alan Katrizky, U. Florida)
Short Course in Heterocyclic Chemistry Nucleophilic Substitution (Prof. Alan Katrizky, U. Florida)
Antiaromaticity (Matthew Burk, Denmark Group)
Aromatic Interactions (Rob Knowles, MacMillan Group)
Pi-stacking Interactions (Larry Wolf, Denmark Group)