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A test from whittier college's organic chemistry course, chem 231b, consisting of questions related to polymers, reactions, and retrosynthesis. Students are required to answer questions about the definition and preparation methods of polymers, explain the acidity differences between ethyne, ethene, and ethane, and predict major products or provide reagents for various reactions. Additionally, students must perform retrosynthetic analysis for a given molecule and propose the best synthetic route.
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Name: Whittier College
125 Points Total April 13, 2003
1a. What is a polymer? Provide a specific example. What are three methods for preparing polymers? Provide a simple example for each method.
1b. Provide an explanation for the fact that ethyne is more acidic than ethene which is more acidic than ethane.
major product for each reaction OR provide the reagents for each synthesis (more than one reaction may be required). Pay Close attention to stereochemistry. Concisely explain your rationale: (64 points
?
NBS / hν
?
OH Br 2 ?
H
3a. Provide a retrosynthetic analysis for this molecule with at least two different synthetic pathways, each resulting in the synthesis of jasmine from 1-methylcyclopentene and any molecule containing three or less carbons. It would be beneficial to think of several different routes. Do not provide a mechanism and ensure that you think about this problem in the proper manner (15 pts)
3b. Choose the best route and provide an appropriately presented synthesis of this molecule (6 points)
O
Jasmone (The pleasant smelling odor of Jasmine flowers)
4a. What is the structure of achiral 3,5-diethylcyclopentene? Why is it considered achiral? (what does that mean?) (2 pts)
4b. How are A, A’, B & B’ all related to each other? Why are different experimental results obtained using the different techniques? (2 pts)
4c. Show a mechanism that accounts for the formation of the major products A & A’ from the hydroboration reaction and explain briefly. (6 pts)