CHEM 769/7690 - Physical Organic Chemistry

Semester: Winter 2021

Professor: A. Schwan | Discipline: Organic | Campus: Guelph

Description

Physical organic chemistry, including a discussion of reactive intermediates, substituent effects, pericyclic reactions, radical chemistry and a basic theoretical description of the bonding in organic molecules.

Method of Presentation: One 2 1/2 hour lecture per week, Tuesday evenings at 7:00 pm by remote, live lectures on TEAMS. First lecture is Tues. Jan. 5, 2021. There will be no lectures during reading week (Feb. 18).

CONTENT OUTLINE

  1. Kinetics and Mechanism

(a)        Transition state theory
(b)       Energy profiles

  1. Substituent Effects on Organic Rates and Equilibria

(a)        Qualitative description of substituent effects

  • Linear free energy relationship: the Hammett equation
  • Acid and Base catalysis
  1. The Hückel Molecular Orbital Method — a tool for appreciating molecular orbitals

(a)        Description of the method
(b)        Regularities in Hückel Molecular Orbitals
(c)        The concept of aromaticity

  1. Aromaticity

(a)        NMR analysis of aromaticity
(b)        Homoaromaticity
(c)        Heterocyclic aromaticity

  1. Orbital Symmetry Control of Concerted Reactions

(a)        FMO analysis of pericyclic reactions
(b)        Introduction to 1,3-dipoles
(c)        Other reactive species in pericyclic reactions

  1. Radical Reactions

(a)        Concepts and BDE’s

  • Prevalence
  • Rearrangements
  1. Evaluation of Some Research Publications

-to take place throughout the year as a class discussion

Materials

Text: Modern Physical  Organic Chemistry, E.V. Anslyn and D.A Dougherty….suggested

The text is a useful reference for most of the topics to be covered in the lectures.  Further references will be given where appropriate.  Supplemental information in the form of class notes are provided.  These will be presented to you in some form in advance of lectures.

Library Reserve List
-due to lack of use in the past, there are no books on reserve in the libraries.

Several useful general texts:
Anslyn and Dougherty as noted above
Felix A. Carroll  Perspectives on Structure and Mechanism in Organic Chemistry
F.A. Carey and R.J. Sundberg    Advanced Organic Chemistry  Part A: Structure and Mechanisms. 5th Ed.
Neil Isaacs Physical Organic Chemistry, 2nd Ed.
T.H. Lowry and K.S. Richardson Mechanism and Theory in Organic Chemistry

Evaluation

The course grade will be based on a final examination, some problem assignments and an essay of one research group’s recent efforts in physical organic or related chemistry. The final examination will be given in April. Regular problem sets will be comprised of a few questions. Several practice problems will be part of the course notes. The absolute final due date for the essay is March 23, 2021.

The final grade will be calculated as follows:

research essay               30%
problem assignments  35%
final examination         35%

Should you wish to drop one of your in-term efforts (once you have completed it and seen your grade) and make the final exam worth the difference, that option is available and should be requested in writing before you write the final.

Lab/Project

Audits: Please understand that an audit is an official entry on your transcript and there are certain course requirements to achieve this. Audit does not mean “sitting-in”. Professor Schwan generally does not recommend the audit or ‘sitting in’ process, since 1. your graduate career will be assessed primarily by the quality of your thesis and 2. a graduate degree means that you can learn things for yourself. It follows that your time should be spent on your research project.

Schedule

  • Tue: 7:00 pm - 9:20 pm in Remote

Office Hours

Office: MacN 336, Guelph Campus. 824-4120 X58781; E-mail: [email protected]; FAX: 1-519-766-1499; Cell: 519-835-8055