Last Year's Exam #3

C3443x EXAM 3
Professor Horne
November 25, 1996

1.(5 pts. ea.) Provide structures and/or a specific example for each of the following (do not use "R" groups):

    a) 	pyridinium chlorochromate		b)  thionyl chloride

    c) 	an ozonide				d) a halohydrin

    f)	a phase transfer catalyst

2. (5 pts. ea.) Indicate the major organic product(s) for the following reactions. Although not specifically indicated, assume acidic work-up when appropriate. Clearly show stereochemistry when appropriate.

3. (10 pts. ea.) Provide a detailed mechanism for the following transformations. Show all arrows and formal charges.

a)

b)

4. (10 pts. ea.) Provide the best possible stereospecific synthetic route to the product from the given starting material. You may use any inorganic and/or organic reagents as needed. The optimal answer for each part consists of a) 5 steps and b) 3 steps.

a)

b)