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Summary: CHM 2220 Organic Chemistry 2220 Winter Term 2010
Problem Set #3 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
Your Name:
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Section Number:
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)).
5 PTS
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.
7 PTS
OMe
CHO
O
O
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