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

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

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

Recent Applications of the Prins Reaction in Stereoselective Synthesis Matthew D. Shair Monday

Carey& Sundberg, Part A, CH 4, pp 187-250 Conformational Analysis-4 a Problems of the Day:(To be discussed) Conformational Analysis of C6 >Cg Rings continued Predict the stereochemical outcome of this reaction

Prelog Strain: van der Waals interactions Baeyer Strain: bond angle distortion away from the ideal Pitzer Strain: torsional rotation about a sigma bond Baeyer Strain for selected ring sizes size of ring Ht of Combustion

Beak, P. (1992). “Determinations of transition-state geometries by the endocyclic restriction test: mechanisms of substitution at nonstereogenic atoms.” Acc. Chem. Res. 25: 215. The Primary Literature

Allylic 1-3-Strain as a Controlling Element in Stereoselective Transformations TSO(2C)4 R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 2054-2070 CH2)lOTs Conformation Design of Open-Chain Compounds

Acyclic Conformational Analysis-1 Ethane, Propane, Butane & Pentane Conformations Introduction to Allylic Strain Reading Assignment for week

Stereoelectronic Effects-1 Anomeric and Related Effects Electrophilic & Nucleophilic Substitution Reactions The SN2 Reaction: Stereoelectronic Effects Olefin Epoxidation: Stereoelectronic Effects Baeyer-Villiger Reaction: Stereoelectronic Effects Olefin Bromination: Stereoelectronic Effects