Page Points

1 ______ (12)

2 ______ (12)

3 ______ (22)

4 ______ (23)

5 ______ (17)

6 ______ (14)


Total ______ (100)

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

(b) (6 pts) Provide structures for the following molecules.

4-ethyl-2-fluoroaniline b-aminobutanoic acid pyridine

2. Circle the most acidic proton(s) in each of the following molecules (6 pts)

Use the sugars below to answer the following questions.

3. Draw the open form of L-mannose as a Fischer projection. (3 pts)

4. Draw the closed pyranose ring form of D-ÿ-galactose as a Haworth projection. (3 pts)

5. Indicate which of the following sugars can undergo mutarotation? (6 pts)

6. Fill in the reagents for the following reactions (there may be more than one step). (16 pts)

7. What esters are required to form the following mixed (crossed) Claisen products? (8 pts)

a.

b.

8. Draw the structures of the products of the following reactions. (15 pts)

9. How many peaks would one see in the 13C nmr spectrum of the following compound. (2 pts)

10. What reactant could yield the following product from an intramolecular Aldol condensation? (3 pts)

11. Draw the reactants used to produce the Aldol condensation product shown below. (4 pts)

12. Predict the products of the following reactions. (8 pts)

13. Draw the Fischer projection of the open form for the following D sugar. (3 pts)

14. Circle the strongest base out of each of the following pairs. (4 pts)

15. Write the keto and enol form of cyclohexanone. (2 pts)

16. The pKa of acetophenone is 16. Calculate the equilibrium constant for the acid-base reaction of acetophenone with sodium ethoxide. The pKa of ethanol is 15.9. First write out the equation for the reaction. (5 pts)