Chemistry 172Q » Spring » Full Semester
4 Credits
Quest Organic Chemistry II
Instructor(s): Bradley L. NilssonPrerequisites: CHM 171Q and CHM 173Q, coregistration in CHM 210.Crosslisting: None.Course Summary:
CHM 172Q 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 Quest 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. Quest 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). 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.
Course Topics:
- Introduction: Conjugated Dienes
- FMO Theory: Dienes and Allylic Systems
- The Diels-Alder Reaction
- Benzene and Aromaticity: The Huckel4n+2 Rule
- Electrophilic Aromatic Substitution/Directing Effects
- Friedel-Crafts Reaction and NucleophilicAromatic Substitution
- Problem-Solving and Synthetic Strategy
- Aldehydes and Ketones:Nucleophilic Addition of H2O
- Alcohol NucleophilesKetals and Acetals
- Nitrogen Nucleophiles,Conjugate Addition
- The Wittig Reaction,Problem-Solving in Synthesis
- Carboxylic Acids, Introduction
- Carboxylic Acid DerivativesNucleophilic Acyl Substitution
- Problem-Solving with Pu
- Carboxylic Acid Derivatives: Conclusion
- Enols and Enolates: Structure and Reactivity
- Aldol Reaction: Examples
- The Aldol Reaction in Synthesis
- Retrosynthetic Analysis of Complex Molecules
- Special Topics I
- The Robinson Annulation/ Michael Reaction รข-Dicarbonyl Compounds/The Claisen Condensation
- Carbonyl Chemistry/ Problem-Solving
- The Mannich Reaction /Problem-Solving
- Electrocyclizations
- Electrocyclizations and Cycloadditions
- Sigmatropic Rearrangements
- Strategies for Drug Development
- Amino Acids and Proteins
- Amino Acid Synthesis/ Protein Synthesis
- Enzyme Chemistry/ Covalent Inhibition
- Enzymes (Competitive Inhibition); Cofactors
Required Text:
Organic Chemistry: Structure and Function, 5th Edition, K. Peter C. Vollhardt and Neil E. Schore
Guide: Study Guide and Solutions Manual for Organic Chemistry: Structure and Function, 5th Edition