CHEM 202 - Mech II

CHEM 202 - ORGANIC REACTION MECHANISMS II

Instructor:
 David Van Vranken      david.vv@uci.edu
 Office hours:  Tue 1-2 pm, RH 2046D
Associate Instructor:
 Stan Hiew      shiew@uci.edu
 Office hours:  Mon 3-4 PM, NSI 4th floor couch area
MEETING TIMES:
 Class (cc 41402): MWF 11-12 am  RH 190 
 Discussion (cc 41403): W 12-1 pm  MSTB 124 - note the room
TEXTBOOK Fleming, I.  Molecular Orbitals and Organic Chemical Reactions. John Wiley&Sons: New York, 2009. Sundberg, R. J. Advanced Organic Chemistry. Part A: Structure and Mechanisms. Springer.
PROBLEM SETS: Problem sets are due on Wednesday at the beginning of Discussion Section.
DISCUSSION SECTION: Teamwork and communication are essential to organic chemistry.  Discussion sections will be based on team problem solving and presentation of answers in front of the class.  This will give you a chance practice discussing chemistry and help me identify (some of) the gaps in my teaching.   In the end, everyone will benefit.
EXAMS:     Exam times are subject to change
 Midterm 1:      Fri, Feb 2
 Midterm 2:      Fri, Mar 2
 Final Exam:     Fri, Mar 23, 8-10 am (Wednesday? TBD)
GRADING:
 Midterm 1                   25%
 Midterm 2                   25%
 Problem Sets              10%
 D.S. Participation        10%
 Final Exam                  30%

Additional Resources

Videos
2014 Videos of Chem 202 Lectures

Other Versions of Chem 201
My web site for Chemistry 201 in Fall, 2012
The lectures for Chem 201 in Fall, 2012 are on YouTube

On Line Search Tools
SciFinder - the definitive search engine for chemical structures
REAXYS - a powerful search engine for searching starting materials, products, rate constants, spectra, natural products, and biologically active molecles
NIST WebBook - thermodynamic data, IR spectra, mass spectra, and more

ReactionPredictor Pierre Baldi's on line tool for predicting arrow-pushing mechanisms

Free Software
MacMolPlt - free software visualizing MOs and charge distribution
COPASI - free software for modeling reaction kinetics
Avogadro - free software for molecular mechanics
TurboMol Demo version - free demo version 

ORGANIC REACTION MECHANISMS I AND II 
I. Arrow-Pushing and Molecular Orbitals
  A. Rules for arrow-pushing
  B. Molecular Orbital Theory
II. Energy and Selectivity
III. Proton Transfers and Acid-Base Equilibrium
IV. Orbitals and Arrow-Pushing
  A. Addition to Empty p Orbitals
  B. Addition to Empty pi* Orbitals
  C. Addition to Empty sigma* Orbitals
  D. Non-Bonding Orbitals as Nucleophiles
  E. Pi Orbitals as Nucleophiles
  F. Sigma Orbitals as Nucleophiles
V. Chemistry of Third Row Atoms
  A. Chemistry of Phosphorus Functional Groups       (End of Chem 201, Fall 2017)
  B. Chemistry of Sulfur Functional Groups                 (Start of Chem 202, Winter 2018)
VI. Conformations
  A. Conformation and Stereoelectronics
  B. Rings and Cyclizations
VII. Pericyclic Reactions
  A. Cycloaddition reactions
  B. Ene reactions
  C. Electrocyclic reactions
  D. Sigmatropic reactions
VIII. Kinetics
  A. Concentration dependence and rate equations
  B. Selectivity and Free Energy
  C. Transition State Theory, Temperature and Half-Lives
IX. Radical Reactions
X. Electron Transfer Reductions
XI. Photochemistry
XII. Modeling chemical reactions and reactivity