MU Chemistry 210 WS97
Catalog of Things-to-Study
Preparation to Final

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The final is comprehensive. The questions will focus on addition reactions and the chemistry of alkenes & alkynes. Relevant issues studied earlier will come up in that context.

Chemistry is about bonding (covalent, polar covalent, ionic, H-bonding, dispersion). We us bonding models (hybridization, resonance) to talk about bonding and the properties that follow (structure, polarity, dipoles, electrophilicity, nucleophility, basicity, acidity, ...). We use stereochemical descriptors to discuss isomeric forms (cis/trans/gauche conformations, cis and trans geometrical isomers, E/Z isomers, R/S isomers, diastereoisomers, D and L in Fischer projections). Reaction chemistry deals with changes in constitution and its regiochemical and stereochemical aspects. This is the stuff of chemistry and that is what I will ask you about.

A good number of questions in the final will deal with synthesis. To master these questions, you need to know a solid body of reaction chemistry. This aspect was lacking in exam 3 and we need to work on it. Here are some guidelines: (1) For every reaction be very clear about substrate, reagents, workup and product. (2) You need to know the reactions so well that you can say what the product is if given the substrate and the reagent (synthetic knowledge), that you know what substrate and reagent to chose to make a given product (retrosynthetic knowledge), and that you know substrate and product if given a certain reagent. I will only ask "mainstream chemistry" and that is what you should focus on.

Our discussions of reaction chemistry always were organized on the basis of common substrates. In your preparations for the final, you should also consider groups of reactions that lead to the same product. For example, could you list a few reactions that lead to epoxides (intramol. Williamson, epoxidation), to diols (hydroxide cleavage of epoxides, osmium tetroxide oxidations), to alcohols ...

There will be a few questions on NMR spectroscopy but they will be relatively straightforward. Know the basics about the number of signals (chemical and magnetical equivalence), chemical shifts (definition, diamagn. shift parallels the positive charge, know anisotropic effects due to double, triple, and aromatic bonds), about splitting patterns (multiplicity according to n+1 rule), and signal intensity (integration).

Addition Reactions - The Chemistry of Alkenes
Knowledge of Preparations of Alkenes (and Acetylenes)
Requires knowledge of elimination reactions
General Knowledge of Addition Reaction Mechanisms
Knowledge of Regiochemical Issues
Markownikov or anti-Markownikow
1,2 versus 1,4-addition
Knowledge of Stereochemical Issues
Anti or syn addition
Stereospecificity in ring formations
Familiarity with the following reactions
Reductions & Oxidations of Alkenes
Hydrogenations (homo and hetero)
Diol Formations
Epoxide formations (MCPBA)
Oxidative methyl ketone formation
Alkene cleavage (complete, three ways including ozonolysis)
Reactions with Alkenes
Note that epoxidations with peroxy reagents are similar.