CHEMISTRY 534

Advanced Organic Chemistry

Physical Organic Chemistry:

Structure and Mechanism

Fall 2015

 

 

 

Syllabus and Course Schedule.

 

Student Learning Outcomes for Chem 534 (B.S. and M.S. Program):

SLO1(m): Demonstrate basic knowledge in the area of organic chemistry. (Assessment tool: course exams)

SLO2(m): Organize and communicate scientific information clearly and concisely, both verbally and in writing (Assessment tool: final project/presentation).

SLO3(m): Effectively utilize the scientific literature to research a chemistry topic (Assessment tool: final project/presentation)

 

Rules for orbital mixing (QMOT).

 

Practice Problem: LCAO.

 

Bonding & MO Theory: Group Orbitals..

 

Additional Practice Problems on Bonding and MO Theory.

 

 

Conformation, Sterics, and Stereoelectronics.

 

Problems in Conformation, Sterics, and Stereoelectronics.

 

Stereochemistry.

 

Problems in Stereochemistry.

 

 

Further Reading on These Topics:

 

Stereoelectronics:

  1. Stereoelectronic Effects, by A.J. Kirby, Oxford Science, 1996.
  2. Stereoelectronic Effects in Organic Chemistry, by Pierre Deslongchamps, Pergamon, 1983.
  3. Frontier Orbitals and Organic Chemical Reactions, by Ian Fleming, Wiley, 1977.

 

Stereochemistry

  1. Stereochemistry of Organic Compounds, E.L. Eliel, S.H, Wilen, and L.Mander, Wiley, 1994.
  2. Stereoselectivity in Organic Synthesis, by Garry Procter, Oxford Science, 1998.

 

 

Kinetics 1.

 

Problems in Kinetics, 1.

 

Kinetics 2.

 

Problems Kinetics 2.

 

Catalysis.

 

Problems in Catalysis.

 

Additional Reading and References:

 

Linear Free Energy Relationships

 

  1. Williams, A. (2003) Free Energy Relationships in Organic and Bioorganic Chemistry, Royal Soc. Of Chem., Cambridge, England.
  2. Fuchs, R., and Lewis, E.S. in Investigation of Rates and Mechanisms of Reactions, 3rd ed., E.W. Lewis (Ed.), Wiley-Interscience, New York, 1974, pp. 777-824.

 

Tunneling

 

  1. Caldin, E.F. “Tunneling in Proton-Transfer Reactions in Solution.” Chem. Rev. 69, 135 (1969)
  2. Bell, R.P. (1980) The Tunneling Effect in Chemistry Chapman and Hall, London.

 

Mechanistic Analysis

 

  1. Williams, A. “The Diagnosis of Concerted Organic Mechanisms.” Chem. Soc. Rev. 93 (1994).

 

Isotope Effects

 

  1. Melander, L., and Saunders, W.A., Jr. (1980) Reaction Rates of Isotopic Molecules, John Wiley & Sons, New York.
  2. Collins, C.J., and Bowman, N.S. (eds.), Isotope Effects in Chemical Reactions, ACS Monograph 167, Van Nostrand Reinhold, New York, 1970.

 

 

Catalysis

 

  1. Cornils, B., Herrmann, W.A, Schloegl, R., and Wong, C.-H (eds.)(2000) Catalysis from A to Z: A Concise Encyclopedia, Wiley-VCH, Weinheim.

 

General and Specific Acid-Base Catalysis

 

1.   Chem. Rev. , 72, 705 (1972)

  1. Acc. Chem. Res. 9, 425, (1976)
  2. Acc. Chem. Res. 13, 161-169, (1980)
  3. JACS, 94, 4731 (1972)
  4. ACIEE 3, 1-19 (1964)

 

 

 

Solutions and Non-Covalent Binding Forces.

 

Problems for Solutions/Non-Covalent Binding Forces.

 

 

Anionic Mechanism Practice

 

Cationic Mechanism Practice

 

Pericyclic Mechanism Practice

 

Radical Mechanism Practice

 

Organometallic Mechanism Practice

 

Mixed Mechanism Practice

 

Instructions for Final Presentation.

 

Grading Rubric for Final Presentation.