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Material Type: Exam; Class: Organic Chemistry II; Subject: Chemistry; University: Whittier College; Term: Spring 2002;
Typology: Exams
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Test # March 20, 2002
1a. What is a chemical polymer? How are they made? Briefly explain and provide an example. ( points)
1b. What is tautomerization? Provide an example and a mechanism for the reaction under acidic conditions. (5 points)
2a.
2b.
2c.
Br
OH
3a. What is the structure for Compound A? (4 pts)
3b. Write a mechanism that accounts for the formation of Compound A? Your mechanism must show the product that results from the first set of reagents (aka Hg(OAc) 2 / H 2 O) not the second set. Please show the overall conversion of the second set of reagents. Include any important transition states in your mechanism. (8 pts)
3c. What are the structures for Compound B & C? (8 pts)
3d. Write ONE mechanism that accounts for the formation of Compound B OR C? Your mechanism must show the product that results from the first set of reagents (aka BH 3 / THF) not the second set. Please show the overall conversion of the second set of reagents. Include any important transition states in your mechanism. (8 pts)
3e. What are the main reasons that help us understand why are there different products from each reaction? (5 pts)
HO
C 8 H 14 O
IR Spectrum: Strong sharp peak at 1125 cm- HO
C 8 H 16 O (^2)
IR Spectrum: Strong Broad peak at 3350 cm-
Make this
From any compound with three carbons or less
4a. Conduct a retrosynthetic analysis for the above problem. Investigate more than one method to make the desired molecule; the various methods do not have to be completely correct, but rather should show that you have thought of alternative routes. (13 points)
4b. Using the best approach from problem 4a, synthesize the desired molecule. Mechanisms are not required, but reagents and conditions are required. (13 points)
