Summary: CHM 2220 Organic Chemistry 2220 Winter Term 2010
Problem Set #3 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
Teaching Assistant's Name:
1) Illustrate the products A, B and C and outline the important enolates that are formed for dictating
the preferred stereochemistry with mechanistic insights. (Use Newman projection(s)).
2) How would you make each diastereomer of the product from the same alkene? 4 PTS
3) How would you attempt to transform this allylic alcohol into both diastereomers of the epoxide
stereoselectively? You are not expected to estimate the degree of success. 4 PTS
4) Here is an outline of the AstraZeneca synthesis of a thromboxane analogue. Explain the
reactions, giving mechanisms for each step, and explain how the stereochemistry is controlled.