1 ______ (18)

2 ______ (27)

3 ______ (21)

4 ______ (27)

5 ______ (07)

Total ______ (100)

1. (a) Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when applicable (i.e cis or trans). (9 pts)

__________________________ __________________________ _____________________

(b) (9 pts) Provide structures for the following molecules.

3-Pentanethiol cis-3-methylcyclopentanecarbaldehyde diphenylether

2. The alkene below can be hydrated via three different procedures to produce an alcohol. Each method produces a different isomer. One proceeds through a rearrangement. Show the products which result from each reaction. (9 pts)

3. Show the structures of the products for each of the reactions below. (18 pts)

4. Show the structures of the products for each of the reactions below. Clearly show stereochemistry. (16 pts)

5. Show a complete arrow pushing mechanism for the following reaction. (5 pts)

6. Fill in the reagents above the arrows to complete the following synthetic route. (6 pts)

7. Show the structures of the products for each of the reactions below. (15 pts)

8. Determine the best choice of reactants to synthesize the following ether using the Williamson Ether synthesis method (alkyl halide and an alkoxide). (2 pts)

9. Rank the following compounds with respect to their reactivity toward bromination with Br2/FeBr3. Label #1 as the fastest and #4 as the slowest. (4 pts)

______ ______ ______ ______

10. Circle the isomer which gives the following 13C nmr spectrum. (3 pts)

11. Circle the structure which gives the following 13C nmr spectrum. (4 pts)