This Exam Is Administered Under the Wake Forest Honor Code

Exam 2 Chemistry 122 March 23, 2009

Do not open or begin this exam until instructed. This exam consists of 5 pages plus the cover page. Before starting the exam, check to make sure that you have all of the pages. The exam has a total of 100 points and includes 10 questions. Only legible answers written on the exam will be considered for grading. All pertinent information needed for the exam is given. Notes and textbooks are not permitted. Use your time wisely.

This exam is administered under the Wake Forest Honor Code. Name______

1. (3 points) Does the following alkene have an E or Z configuration? Show your reasoning for full credit.

2. (6 points) Provide electron-pushing arrows to indicate the flow of electrons in each step of the following reaction. Just as in a similar homework problem, you will need to redraw one of the structures so you can clearly indicate the particular bond that is breaking.

O O O O CH NH O O 3 2 + O O NH2CH3 O NH2CH3

O O + NHCH3 HO

3. (4 points, 2 each) Calculate the oxidation state of the indicated carbon atoms.

CH3CH CH C OH

4. (4 points, 2 each) Classify each of the following reactions as substitution, elimination, addition, or rearrangement reactions.

H2SO4 

Br + (CH3)3COK + KBr + (CH3)3COH  2 5. (4 points, 2 each) Circle the strongest base in each set.

a) CH3CH3 CH3NH2 CH3OH

CH3OH2 CH3OH CH3ONa

6. (6 points, 2 each) Circle the strongest acid in each set.

a) OH OH ONa ONa

b) HC CH H2C CH2 CH3 CH3

c) O O O

CH3 C OH O2NCH2 C OH FCH2 C OH

7. (15 points, 5 each) For each of the following Bronsted-Lowry acid/base reactions a) provide products that would form if the reaction proceeds as written. b) label the acid and base on each side of the reaction. c) draw an arrow indicating which way the equilibrium actually lies.

CH3CH2SH + CH3Li

OH NH Cl + 3

O + ONa OH

3 8. (28 points, 4 each) Provide the major organic product for each of the following reactions. Include stereochemistry where necessary.

1) BH3, THF

2) H2O2, NaOH, H2O

OsO4 (cat.) HIO4

NMO H2O, THF

4 9. (16 points, 4 each) Provide the missing reagent(s) for the following reactions. a)

b) HCH3 Br2 Br Br CHCl3 HCH2CH3

c) 1) O 3 O O +

2) Zn, H2O

d) ROOR

n  Ph Ph Ph

5 10. (14 points) Provide an electron-pushing mechanism and an energy diagram for the following reaction. Label the energy diagram in such a way that I can tell what structures in your mechanism correspond to what point on the energy curve. You do not need to draw transition state structures, but do label transition states on the energy diagram as “TS1” etc. as needed.

HBr Br