I am constantly growing as an educator and continually revising and redeveloping these problem sets. In their most current iteration, which was driven by a personal pedagogical evolution, I’ve moved away from course specific problem sets to a series organized by specific topics. First, topic driving problem sets allow for living documents that can be modified to suite various course layouts and future curricular changes.  Secondly, and more importantly, topic aligned problem sets allow students to asses their understanding on a particular area rather than a series of topic linked together.  This allow students (and me) to more specifically identify areas of disconnect and enhances student learning.  

First Semester Organic Chemistry

  1. Molecular Representation and Bonding (solutions)- Molecular Formulas, Lewis Dot Structures, Condensed Formula, Line-angle (AKA-skeleton notation), Hybridization, Constitutional Isomers and Bonding
  2. Functional Groups and Physical Properties of Organic Molecules (solutions)- Identification of functional groups and how structure affects a molecules boiling and melting points. 
  3. Resonance #1 (solutions) - Introduction into drawing resonance forms and pushing electrons
  4. Resonance #2 (solutions) - More advanced resonance problems
  5. Bronsted-Lowery Acid-Base Chemistry (solutions) - Trends in pKa values and predicting acid-base products and equilibria  
  6. Quiz #1 Review (solutions) - Functional groups, acid/base chemistry, hybridization and bonding
  7. IR Spectroscopy (solutions) - Identifying functional groups from IR spectra
  8. Conformations of Cyclohexane (solutions) - Drawing and Identifying the most stable chair conformations
  9. Relationship Between Molecules (solutions) - Challenge Problems
  10. NMR Problem Set #1 (solutions)- Determining the number of unique hydrogens and carbons in a molecule
  11. NMR Problem Set #2 (solutions)- Predicting the proton spectrum of various organic molecules
  12. NMR Problem Set #3 (solutions)- Structure determination from spectra (proton and carbon NMR)
  13. NMR Problem Set #4 (solutions)- More practice problems, structure determination from spectra (proton and carbon NMR)
  14. Sn1 and Sn2 Reactions (solutions)- looking at the difference between Sn1 and Sn2.  Challenge mechanism.
  15. Sn1 and Sn2 Reactions (solutions)- more practice problems with mechanisms

Second Semester Organic Chemistry

  1. Synthesis Problems (solutions) - Synthesis problems featuring reactions of alcohols, epoxides, and Grignards reagents
  2. Mass Spectrometry (solutions) - Matching mass-spectrum to compounds
  3. NMR and Mass Spec. (solutions) - Determine molecular structure from NMR and MS.
  4. Carboxylic Acts and Derivatives (solutions)- Predict the products, reagents or starting materials, synthesis practice, mechanism practice.