InfoCoBuild

Chemistry 201: Organic Reaction Mechanisms I

Chemistry 201: Organic Reaction Mechanisms I (Fall 2012, UC Irvine). Instructor: Professor David Van Vranken. Why is it that organic chemists can't seem to agree on how to draw plausible arrow-pushing mechanisms? In this course we connect frontier molecular orbital theory and mechanistic arrow-pushing in elementary reaction steps. By equating the interactions between filled orbitals and un-filled orbitals with curved arrows, and distinguishing them from Coulombic interactions, we collimate seemingly endless depictions into a plausible few.

Arrow Pushing


Lecture 01 - Arrow Pushing, Part 1
Lecture 01 - Arrow Pushing, Part 2
Lecture 02 - Molecular Orbital Theory
Lecture 02 - Molecular Orbital Theory (cont.), Energy
Lecture 03 - Energy
Lecture 04 - Selectivity
Lecture 05 - Carbocations
Lecture 06 - Carbocation Stabilization by Vicinal Sigma Bonds
Lecture 07 - Non-classical Carbocations (cont.), Neighboring Groups
Lecture 08 - Neighboring Groups in Ionization Reactions and Solvation
Lecture 09 - Addition to Sigma Star: Proton Transfer
Lecture 09 - Addition to Sigma Star: Proton Transfer (cont.), S_N2 Reactions
Lecture 10 - Addition to Sigma Star: S_N2 Reactions (cont.), Migratory Displacements
Lecture 11 - Eliminations
Lecture 11 - Eliminations (cont.), Addition to Pi Star
Lecture 12 - Addition to Pi Star (cont.)
Lecture 12 - Addition to Pi Star (cont.)
Lecture 13 - Anions
Lecture 13 - Anions (cont.), Alkali Organometallics
Lecture 14 - Alkali Organometallics (cont.)
Lecture 14 - Alkali Organometallics (cont.), Electrophilic Addition to C=C
Lecture 15 - Electrophilic Addition to C=C (cont.)
Lecture 15 - Electrophilic Addition to C=C (cont.) & Lecture 16. C-C Bonds
Lecture 17 - Enols, Enamines and Enolates
Lecture 19 - Sulfur Chemistry
Lecture 20 - Phosphorus Chemistry

References
Chemistry 201: Organic Reaction Mechanisms I
Instructor: Professor David Van Vranken. Frontier orbitals and arrow-pushing mechanisms. Course Info. Lectures. Problem Sets. Links.