CH 201 Name______________________________

Exam #3

October 30, 2002

Page Points

1 ______ (09)

2 ______ (38)

3 ______ (20)

4 ______ (14)

5 ______ (14)

6 ______ (05)

Total ______ (100)

1. a. Provide IUPAC names for the following molecules (don’t forget stereochemistry). (9 pts)

______________________________ ___________________________

______________________________

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

(E)-3,3,5-trimethyl-1,5-heptadiene (Z)-2,3-dichloro-2-butene

2. Predict the products of the following reactions showing the proper stereochemistry and regiochemistry. (32 pts)

3. In each group of compounds below, circle the compound expected to have the lowest heat of hydrogentation. (4 pts)

4. What reagents are neccassary to perform the following transformations. (16 pts)

5. Show an arrow pushing mechanism for the following reaction. (8 pts)

6. The following energy vs reaction coordinate diagram is for the addition of HBr to 2-methylpropene. Label the diagram by filling in the boxes with the appropriate structures (there are 3 of them a,b and c). (6 pts)

7. Predict the product of the following reaction. (4 pts)

8. Predict the product(s) of the following reaction. Show an arrow pushing mechanism showing the formation of each product. Use wedges and hatches and clearly label any stereocenters! (10 pts)

9. Given the equation: DG = DH- TDS predict whether the following reaction becomes more or less exergonic when the temperature is raised. Please circle: More or Less

(3 pts)

10. Draw the structure of the allyl alcohol. (2 pts)