CH 201 Name ______________________________

Exam #5

December 13, 2002

Page Points

1 ______ (08)

2 ______ (27)

3 ______ (21)

4 ______ (08)

5 ______ (21)

6 ______ (10)

7 ______ (05)

Total ______ (100)

1. Provide IUPAC names for the following molecules. (4 pts)

______________________________ ____________________________

2. Provide structures for the following molecules. (4 pts)

tert-butyl benzyl ether THF

3. Predict the products of the following reactions, showing stereochemistry where appropriate. You need not show the mechanisms for these reactions; simply draw the structures of the products. (27 pts)

4. Fill in the appropriate reagents to carry out the following reactions. (21 pts)

5. Fill in the appropriate reagents to carry out the following reactions. (8 pts)

6. Predict the products of the following reactions, showing stereochemistry where appropriate. You need not show the mechanisms for these reactions; simply draw the structures of the products. (21 pts)

7. Circle the alcohol and alkyl halide one would use to make the following ether using the Williamson Ether synthesis. (4 pts)

8. Label the following compounds by solubility in water. (3 pts)

1 = least soluble and 3 = most soluble

9. Rank the following compounds by boiling point. (3 pts)

1= lowest boiling point and 3 = highest boiling point

Synthesis

10. Show all the steps necessary to carry out the following conversion. (5 pts)