CH 202 Name ______________________________

Exam #4

April 16, 2003

Page Points

1 ______ (09)

2 ______ (12)

3 ______ (24)

4 ______ (15)

5 ______ (24)

6 ______ (11)

7 ______ (05)

Total ______ (100)

1 (a) Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when applicable. (6 pts)

(b) (3 pts) Provide structures for the following molecules.

ethylacetate 2-methyl butanoyl chloride N-ethylbenzamide

2. Show the mechanism for an acid catalyzed esterification of the acid shown below. (6 pts)

3. Show a complete arrow pushing mechanism for the following reaction. Show all steps, include all charges, and draw arrows to show electron flow. (6 pts)

4. Fill in the reagents for the following reactions. (24 pts)

5. Predict the products for the following reactions. (15 pts)

6. Predict the products for the following reactions. (24 pts)

7. Rank the following acids assigning 1 to the strongest the strongest acid and 3 to the weakest. (3 pts)

8. Show the starting materials that were used to make the following Claisen product. (4 pts)

9. Show the starting materials that were used to make the following Aldol product. (4 pts)

10. Synthesis Problem. Show a synthetic route to carry out the following transformation. (5 pts)