159 Chemistry Research Laboratory
West Virginia Univeristy
joshua.osbourn@mail.wvu.edu
Chemistry 531 - Physical Organic Chemistry
Fall 2019
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Textbook - Modern Physical Organic Chemistry by Anslyn & Dougherty
Supplemental Text - Advanced Organic Chemistry by Carey & Sundberg - eBook*
Not Voodoo - Synthetic Chemistry Lab Techniques
Advanced Organic Chemistry Lecture Notes - Harvard
0. Review of Sophomore Organic Chemistry
- Organic I Review Sheets
- Must Know pKa Values
- Reading: MPOC Appendix 5 - Pusing Electrons
- Homework: Appendix 5 Practice Problems
- Chapter 0 Lecture Notes
I. Bonding & Intro to Molecular Orbital Theory [MPOC Ch 1]
- Reading: MPOC 1.1
- HW: 1, 2, 6, 7, 12, 18
- Reading: Intro to Orbitals
- HW: 3.30, 3.31, 3.33, 3.37, 3.40, 3.41 -- HW Solns
- Reading: Intro to MO Theory
- HW: D.1, D.3, D.5, D.7, D.8 -- HW Solns
- The definitive "Frontier Orbitals" book by Fleming - eBook*
- Stereoelectronic Effects - eBook*
- FMO Handout
- Baldwin's Rules Handout
- Revision of Baldwin's Rules [Chem. Rev. 2011, 111, 6513]
- Felkin-Anh & Cram Chelate Practice Problems --- Answer Key
- Felkin-Anh & Cram Chelate Video
- Chapter 1a (Molecular Structure) Lecture Notes
- Chapter 1b (MO Theory) Lecture Notes
IIa. Thermodynamics [MPOC Ch 2]
- Reading: MPOC 2.1 & 2.2
- HW: 8, 16, 23, 36, 50
- Bond Dissocation Energy Values [Acc. Chem. Res. 2003, 26, 255]
- Bond Dissociation Energies - Simplified List
- Benson's Group Increment Tables
- Chapter 2a (Energy) Lecture Notes
IIb. Conformational Analysis [MPOC Ch 2]
- Reading: MPOC 2.3 & 2.4
- HW: 6, 9, 10, 11, 13, 20, 26, 34, 35
- Reading: Conformational Effects on Reactivity (from C&S)
- Cyclohexane Conformational Analysis
- Chapter 2b (Conformational Analysis) Lecture Notes
III. Acids and Bases [MPOC Ch 5]
- Reading: MPOC 5.1-5.4, 5.6
- HW: 2, 3, 5, 6, 7, 9, 11, 14,19, 21, 22
- Evans pKa Table
- Some Common pKa Values to Know
- Chapter 5 (Acids & Bases) Lecture Notes
IV. Stereochemistry [MPOC Ch 6]
- Sophomore Organic Stereochem Review
- Reading: MPOC 6.1-6.5, 6.9
- HW: 3, 5, 7, 8, 9, 17, 22, 23, 32
- Extra Practice Problems --- Answer Key
- Isomerism Flow Charts: Version A --- Version B
- Stereoselectivity vs Stereospecificity
- Online 3D Model Builder - MolView
- Stereochemistry Workbook eBook*
- Chapter 6 (Stereochemistry) Lecture Notes
V. Reaction Kinetics [MPOC Ch 7]
- Reading: MPOC 7.1 - 7.3, 7.4 (skim), 7.5, 7.6 (skim), 7.8
- HW: 2, 5, 8, 11, 13, 15, 16, 17 (click on 15 & 16 for extra details)
- Practice Problem Set (skip Q6) --- Answer Key
- TS Theory - Example Excel Graph
- Video - ReactIR
- Chapter 7 (Kinetics) Lecture Notes
VI. Experiments to Determine Reaction Mechanisms [MPOC Ch 8]
- Reading: MPOC 8.1.1-8.1.3, 8.2, 8.3, 8.5, 8.8
- HW: 9, 11, 12, 14, 15, 18, 19, 20, 21
- Guide to Deducing a Reaction Mechanism
- Video - Visual Kinetic Isotope Effect
- Sigma Values for Hammett Plots
- Newcomb Radical Clocks
- Radical Clocks - Review Article
- Chapter 8 (Mechanism Experiment) Lecture Notes
VII. Pericyclic Reactions [MPOC Ch 15]
- Reading: MPOC 15.1, 15.2, 15.3.1-15.3.5, 15.4, 15.5
- HW: 2, 7, 10, 11, 15, 17, 26, 27, 32, 33
- Additional Practice Problems --- Answer Key
- Chapter 15 (Pericyclic Reactions) Lecture Notes
VIII. Nucleophilic Substitution Reactions [MPOC Ch 11]
*eBook is available for free access via the WVU Library.
Quizzes
- Quiz 1 --- Answer Key
- Quiz 2 --- Answer Key
- Quiz 3 --- Answer Key
- Quiz 4 --- Answer Key
Past Exams