Key concepts

Predict the product and show the mechanism for the reaction of methyl vinyl ketone with 2-methylcyclohexane-1,3-dione in the presence of base. The Logic: Michael Addition:

Michael Addition followed by Intramolecular Aldol Condensation. Critical Thinking:

Compare and contrast the mechanisms of the Sharpless Asymmetric Epoxidation (SAE) and the Jacobsen Epoxidation. Which substrate classes are best suited for each method? Draw the transition state for the SAE of geraniol using (+)-DET.

You are staring at a complex pericyclic transition state. Panic sets in. Here is your 15-minute workflow:

Explain why the Hammett ρ value for the solvolysis of substituted benzyl chlorides is -4.5, while for the ionization of substituted benzoic acids it is +1.0.