Page Points BDE (kJ/mole)

1 ______ (14) (CH3)3C--H 401

2 ______ (15) H-Br 366

3 ______ (29) H-Cl 431

4 ______ (20)

5 ______ (12)

Total ______ (90)

1. a. Provide IUPAC names for the following molecules (don't forget stereochemistry). (6 pts)

________________________ ___________________________

b. Provide structures for the following molecules. (4 pts)
(Z)-2,3-dichloro-2-butene (E)-3-methyl-3-octene

2. Calculate the unsaturation number for each of the following compounds. (4 pts)
a. C10H16O b. C10H14N2

3. Calculate the percentage of the monocholorinated products A and B formed in the following free radical chlorination given the fact that tertiary C-H atoms are abstracted 5.3 times faster than primary C-H atoms. Show all work. (5 pts).

4. Orlon has the following general formula. What monomer is it synthesized from? (2 pts)

5. Given the bond disassociation energies on the front page calculate the DH for each of the reactions below. (8 pts)
a. DH

b. Draw a reaction coordinate diagram for each reaction above based on your calculated enthalpy changes.

c. Based on your reaction coordinate diagram draw transition state structures for each reaction on the diagram and indicate clearly which one has developed more radical character on the carbon.

6. Compound A below has a heat of hydrogenation 42 kJ/mole larger than compound B. (5 pts)
a. Which compound is more stable A or B? ________
b. Provide an explanation.

7. Predict the products of the following reactions showing the proper stereochemistry and regiochemistry. (24 pts)

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

9. Predict the products of the following reactions showing the proper stereochemistry and regiochemistry. (15 pts)

10. The following reactions yield the same product. (7 pts)

a. Draw the structures of the product for each reaction after the arrows.

b. For each reaction show the intermediate formed from protonation of the alkene.

c. Draw a reaction coordinate diagram for first step of each reaction on the same diagram. Using this diagram predict which alkene reacts faster.

11. Show an arrow pushing mechanism for the formation of the product shown. (5 pts)