NAME (print): ______________________________________________________________

TA:_____________________ Section Day:_________________ Section Time:__________

Take a few moments to look over the exam. Answer each question on the exam paper.

Important clues and instructions are in bold.

Do all preliminary drawing or computations on the work sheets at the end of the exam. The

work sheets will not be graded. There is a Periodic Table on the last page of the exam.

The exam is 55 minutes.

STOP writing and hand in your exam when you are asked to do so.

REMEMBER: Neatness is to your advantage.

1. (25 pts) ______

2. (25 pts) ______

3. (25 pts) ______

4. (25 pts) ______

_______________________________

Total (100 pts)

1. (5 x 5 pts. = 25 pts.) Provide the products in each of the following chemical reactions. Pay

attention to stereochemistry.

2. (5 x 5 pts. = 25 pts.) Circle the best answer in each of the following:

a) The molar ratio of CrO₃ to RCH₂OH required in the complete oxidation of a primary

alcohol to a carboxylic acid.

2/3

1/6

1/1

3/2

4/3

b) The compound(s) with the highest oxidation level

c) The operational equivalent of the reaction of an olefin with O₃ followed by (CH₃)₂S:

KMnO4 cold

KMnO4 warm

KMnO4/ cat. OsO4

H2O2/cat. OsO4

HIO4/cat. OsO4

d) If a 1N solution requires 49 g of H₂SO₄ per liter of aqueous solution, then a 1N solution of Jones's

reagent (CrO₃/aq. H₂SO₄ ) requires how many grams of CrO₃ per liter of aqueous solution?

100

67

33

49

98

e) A chemical pathway leading from ethane to acetic acid involves a change of how many

electrons?

-4

-2

+4

-6

+6

3. (25 pts.) Compound A, C8H16, reacts with OsO4/H2O2 to give (±)-diol B. Compound A does NOT give n-octane upon catalytic hydrogenation. Monotosylation of B gives alcohol C, which when treated with KOH, gives meso compound D, C8H16O. Exposure of diol B to periodic acid (HIO4) provides a single compound E, C4H8O. Compound E is inert toward pyridinium chlorochromate (PCC) in CH2Cl2. However, the addition of some water to the reaction mixture affords F, C4H8O2. What are the structures A - F? Justify your answers.

4. (25 pts.) Show how you would convert cyclohexanone 1 into 2,7-dimethyl-2,6-octadiene

2. The only other source of carbon available for the synthesis is methyl alcohol. All

reagents and carbon-based solvents are available.