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Final Exam: Thursday 12/13 from 2-4 pm in Clark 320

Course Syllabus

Textbook - Modern Physical Organic Chemistry by Anslyn & Dougherty

Supplemental Text - Advanced Organic Chemistry by Carey & Sundberg - eBook*

Other Recommended Books

Organic Data Tables

Not Voodoo - Synthetic Chemistry Lab Techniques

Advanced Organic Chemistry Lecture Notes - Harvard

I. Review of Sophomore Organic Chemistry

• Organic I Review Sheets
• Must Know pKa Values
• Reading: MPOC Appendix 5 - Pusing Electrons
• Homework: Appendix 5 Practice Problems

II. 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]

III. 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

IV. 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

V. 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

VI. 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*

VII. 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

VIII. 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
• Video - Visual Kinetic Isotope Effect
• Sigma Values for Hammett Plots
• Newcomb Radical Clocks
• Radical Clocks - Review Article

IX. 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

X. Nucleophilic Substitution Reactions [MPOC Ch 11]

• Reading: MPOC 11.5 and/or Carey & Sundberg Ch 4
  • HW: 1, 5, 13, 14 (what stabilizes + in each), 18, 19, 46, 49, 51, 52a, 52b

*eBook is available for free access via the WVU Library.

Quiz and Exam Answer Keys

• Quiz 1 --- Answer Key
• Quiz 2 --- Answer Key
• Quiz 3 --- Answer Key
• Quiz 4 --- Answer Key
• Exam 1 Answer Key
• Exam 2 Answer Key