CH 201 Name ______________________________

Exam #4

November 25, 2002

Page Points

1 ______ (10) Table of Bond Dissociation Energies

2 ______ (20) Bond DHo(kJ/mole)

3 ______ (18) Cl-Cl 242

Br-Br 192

4 ______ (10) I-I 150

H-Cl 431

5 ______ (12) H-Br 366

H-I 297

6 ______ (09) CH3-H 438

CH3-Cl 349

7 ______ (21) CH3-Br 293

CH3-I 234

(CH3)3C--H 381

Total ______ (100)

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

______________________________ ____________________________

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

3-Chloro-1,2-propanediol (Z)-5-Methyl-2-hexen-1-ol Allyl alcohol

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. (15 pts)

4. Write a complete arrow pushing mechanism (show arrows and charges) for the following reaction. (5 pts)

5. Fill in the appropriate reagents to carry out the following reactions. (18 pts)

6. Show an arrow pushing mechanism for the solvolysis reaction below. (6 pts)

7. Show the initiation step and the 2 chain propagating steps in the mechanism which give rise to the product shown in the following reaction (8 pts)

Initiation:

Step (1):

Step (2):

b. Calculate the DH for the first step. Show your work. Circle your final answer. (See table on the first page).

∆H for Step (1) in part a:

8. The following alkyl halide undergoes an E2 elimination reaction with ethoxide, draw the major product. (4 pts)

9. The following molecule undergoes an E2 elimination reaction. Circle the major product. Partial credit can only be given if you draw out the reactive conformation. (4 pts)

10. Rank the following by writing the numbers 1, 2, or 3 in the blanks.

Most soluble in water: 1 = least, 3 = most

11. Circle the compound with the highest Boiling point. (4 pts)