Chemistry 204 » Spring » Full Semester
4 Credits
Organic Chemistry II
Instructor(s): Benjamin Hafensteiner

Prerequisites: CHM 203 (w/grade of C- or better) & CHM 207 or equivalent. Coregistration in CHM 208 or CHM 210 is required.
Crosslisting: None.

Course Summary:
A continuation of a two-semester sequence in the study of organic chemistry. Topics covered include the reactivity of various functional groups, approaches to organic synthesis, reactivity of conjugated systems and molecules of biological significance. There are three 50 minute lectures and one workshop per week. Coregistration in CHM 208 or CHM 210. Grade of C - or better in CHM 203 (or equivalent). 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 Nucleophiles: Ketals and Acetals
  10. Nitrogen Nucleophiles: The Wittig Reaction
  11. Nucleophilic Addition to Carbonyl Compounds: Mechanistic Unity
  12. Carboxylic Acids, Introduction
  13. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
  14. Enols and Enolates: Structure and Reactivity
  15. Aldol Reaction: Examples
  16. The Aldol Reaction in Synthesis
  17. Enols and Enolate Chemistry: Mechanisms & Problem-Solving
  18. The Robinson Annulation/ Michael Reaction
  19. Chirality in Reactions of Carbonyl Compounds
  20. b -Dicarbonyl Compounds/The Claisen Condensation
  21. Carbonyl Chemistry/ Problem-Solving
  22. The Mannich Reaction /Problem-Solving
  23. Electrocyclizations
  24. Electrocyclizations and Cycloadditions
  25. Sigmatropic Rearrangements
  26. Amino Acids and Proteins
  27. Amino Acid Synthesis/ Protein Synthesis
  28. Enzyme Chemistry/ The Catalytic Triad
  29. The pharmacology of opiates
  30. Enzyme Chemistry & Drug Discovery
  31. Enzyme Chemistry: Covalent Inhibition
  32. Enzyme Chemistry: Competitive Inhibition

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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