CH630 Physical Organic Chemistry
Oregon State University
Fall 2009

Instructor: Paul H.-Y. Cheong
Lectures: Weniger 287, MWF 9AM
Office: Gilbert 303
Office Hours: drop in or by appointment
Phone: 737-6760
E-mail: paulc(at)science.oregonstate.edu
Website: http://www.chemistry.oregonstate.edu/cheong/

Course text:
Advanced Organic Chemistry - Structure and Mechanisms (Part A), Francis A. Carey and Richard J. Sundberg, 5th Edition, Kluwer/Plenum: New York, 2007

Objective:
The goal of this class is for you to recognize, rationalize, and understand the fundamental ideas that underly our current understanding of organic chemistry.


Topics:
constructions, trends, generalizations, rules, reactivities, HOMO/LUMO, Frontier Molecular Orbital (FMO) Theory, Hückel MO (HMO), Frost diagrams, symmetries, overlaps, alignment, energies, stereoelectronics, basic Woodward-Hoffman rules
rotational barriers, Boltzman distribution, A-values, stereoelectronics, ring strain, Baldwin's rules for ring closure, effects on reactivity
cations, carbanions, radicals, diradicals, triradicals, carbenes, generation, structure, substituent effects, hybridization effects, reactive pathways
kinetic vs thermodynamic, Lewis, Brönsted, enolizations
electrostatic potentials, formal charges, oxidation numbers
concerted/stepwise, synchronous/asynchronous, classifications
bond dissociation energies (BDE), resonance stabilization energies (RSE), interaction energies
enantiomers, diastereomers, prochiral relationships

Grading policy:

Total = 25% Mid-Term Exam + 25% Paper + 50% Final Exam



Paper:
Due Date: First draft (Nov. 9), Final draft (Nov. 23), Peer review (Dec. 2)
Reference format: JACS style + full titles
Manuscript format: JACS communications template
Schemes and Figures: ACS style
Page lengths: Minimum of 3, Maximum of 5
Sections: History, explanations, discoverer, refs, examples, applications
To be handed in: 1st draft and final, MS Word document format (doc or docx)
Grading method: Peer reviews (25%) x2 + PHYC review (50%)
Paper Topics: Must be pre-approved by PHYC, suggestions below.

Possible topics:
Frontier Molecular Orbital Theory, Relativistic Effects, Torsional Steering, Halogen Bonding, Hydrogen Bonding, Four center two electron bonds, Helical chirality, Axial chirality, Asymmetric Autocatalysis, Nonlinear Effects in Stereoselectivity, Lock and Key Principle, Lipinsky’s Rule, Electrostatic interactions, Steric interactions, van der Waals interactions, Charge transfer, BeMaHaPoThLe, Hard & Soft.


Important dates:
Last day to drop a class by Web: October 9, 11:55 PM
Last day to register or add a class by Web: October 9, 5 PM
Thanksgiving Holiday: November 26–27
Dead week: November 30–December 4
Finals week: December 7–11
End of term: December 11
Final grades due in Registrar’s Office: December 14, Noon
Grades available on Web: December 16