Here is a typical carbonium ion question that you should be able to handle by the end of the course. Write out a mechanism for the following transformation

Introduction to Carbonium Ions Carbocation Stabilization Carbocation Structures by X-ray Crystallography Vinyl & Allyl Carbonium Ions Carbocations: Stability & Structure March, Advanced Organic Chemistry

Bonding Considerations: Carbon vs Silicon Chem 206 Bonding Considerations: Carbon vs Silicon

Chemistry 206 Advanced Organic Chemistry Handout 27A Vicinal Elimination Reactions: An Overview Matthew D. Shair Wednesday

Sulfur-Based Activating Groups Sulfur-Ylides Sulfur-Stabilized Carbanions: Structure Sulfone-Based Transformations Pummerer Rearrangement

Krista Beaver Synthetic Applications of α-Diazocarbonyl Derivatives Chem 206 Synthetic Applications of α-Diazocarbonyl Compounds An Evans Group Afternoon Seminar Krista Beaver January 15, 1999 Leading References:

Nitro and Diazo Groups Historical Perspective Charge Affinity Patterns Functional Group Classification Scheme The Chemistry of the –NO2 Group

Leading References: Langer, P. Angew. Chem. Int. Ed. Engl. 2000, 39, 3049-3052. Ciganek, E. Org. React. 1997, 51, 201-350. Basavaiah, D.; et. al. Tetrahedron, 1996, 52, 8001-8062. Drewes, S. E.; Roos, G. H. P. Tetrahedron, 1988, 44, 4653-4670

Double Stereodifferentiating Aldol Reactions The Mukaiyama Aldol Reaction Variant Allylmetal Nucleophiles as Enolate Synthons

Relevant Background Reading Chemistry 206 Advanced Organic Chemistry Lecture Number 28 Ambiphilic Functional Groups–3