Chemistry 172 » Spring » Full Semester
4 Credits
Freshman Organic Chemistry II
Instructor(s): Joshua L. Goodman

Prerequisites: CHM 171 and CHM 173, coregistration in CHM 210.
Crosslisting: None.

Course Summary:
CHM 172 is a continuation of a one year exploration of the basic observations, concepts and practice of organic chemistry, with a focus on the fundamental relationships among molecular structure and chemical reactivity. The exploration will require that students grapple indepth issues: defining questions, evaluating evidence, weighing arguments, reflecting on epistemological issues, constructing new experiments, etc. The study of organic chemistry (focusing on chemical bonding, structure and stereochemistry, reactions and reaction mechanisms of organic compounds) will be carefully integrated with a review of the key concepts from general chemistry. Freshman Organic is designed for first year students with good preparation in chemistry (e.g., two years of general chemistry and an Advanced Placement score 4 or 5, or equivalent preparation). This sequence fast tracks students to more advanced chemistry courses and the fulfillment of degree requirements in other disciplines. Coregistration in CHM 210 (laboratory and lab/lecture) is required. There are lectures and one workshop per week. The workshop is an informal, interactive two-hour session in which small groups of students work on specially designed problems under the guidance of a trained leader. The purpose of the workshop is to provide a mechanism for students to work actively with the material and with each other. This course uses the Tuesday/Thursday 8:00 - 9:30 am Common Exam time.

Course Topics:
  1. Introduction: Conjugated Dienes
  2. FMO Theory: Dienes and Allylic Systems
  3. The Diels-Alder Reaction
  4. Benzene and Aromaticity: The Huckel4n+2 Rule
  5. Electrophilic Aromatic Substitution/Directing Effects
  6. Friedel-Crafts Reaction and NucleophilicAromatic Substitution
  7. Problem-Solving and Synthetic Strategy
  8. Aldehydes and Ketones:Nucleophilic Addition of H2O
  9. Alcohol NucleophilesKetals and Acetals
  10. Nitrogen Nucleophiles,Conjugate Addition
  11. The Wittig Reaction,Problem-Solving in Synthesis
  12. Carboxylic Acids, Introduction
  13. Carboxylic Acid DerivativesNucleophilic Acyl Substitution
  14. Problem-Solving with Pu
  15. Carboxylic Acid Derivatives: Conclusion
  16. Enols and Enolates: Structure and Reactivity
  17. Aldol Reaction: Examples
  18. The Aldol Reaction in Synthesis
  19. Retrosynthetic Analysis of Complex Molecules
  20. Special Topics I
  21. The Robinson Annulation/ Michael Reaction รข-Dicarbonyl Compounds/The Claisen Condensation
  22. Carbonyl Chemistry/ Problem-Solving
  23. The Mannich Reaction /Problem-Solving
  24. Electrocyclizations
  25. Electrocyclizations and Cycloadditions
  26. Sigmatropic Rearrangements
  27. Strategies for Drug Development
  28. Amino Acids and Proteins
  29. Amino Acid Synthesis/ Protein Synthesis
  30. Enzyme Chemistry/ Covalent Inhibition
  31. Enzymes (Competitive Inhibition); Cofactors

Required Text:
Organic Chemistry: Structure and Function, 6th Edition, K. Peter C. Vollhardt and Neil E. Schore
Guide: Study Guide and Solutions Manual for Organic Chemistry: Structure and Function, 6th Edition

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