2010 Exam#3 - Illustrate your explanations with correct...

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First Three Letters of Last Name NAME _______________________ Network ID__ _____________________ Section_______________________ C HEMISTRY 236 S PRING 2010 E XAM III A PRIL 2, 2010 Note: The last page of this exam is a periodic table. 1 (24) 2 (10) 3 (18) 4 (10) 5 (23) 6 (15) 100
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CHEM 236 Spring 2010 Exam III 2 1. [24 points] Fill in the blanks with the correct product(s), demonstrating correct stereochemical outcomes. (3 points per blank)
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CHEM 236 Spring 2010 Exam III 3 2. [10 points] Over each arrow, declare whether the transformation shown is an oxidation, a reduction, or neither. (2 points per arrow)
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CHEM 236 Spring 2010 Exam III 4 3. [18 points] Consider the following pair of reactions: a) Explain the difference in reactivity between the two ether groups in compound A. (6 points) b) Explain the different regiochemical outcomes of these two reactions.
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Unformatted text preview: Illustrate your explanations with correct mechanisms. (12 points) CHEM 236 – Spring 2010 Exam III 5 4. [10 points] Provide mechanisms for the following transformations (5 points each): CHEM 236 – Spring 2010 Exam III 6 5. [23 points] Consider the following series of reactions: a) What are the structures of B and C? What is the stereochemical relationship between them? (7 points) b) What is the mechanism of the reaction of A with mCPBA? (5 points) c) What are the structures of D and E? (6 points) d) Explain the different reactivites of D and E with HIO 4 . (5 points) CHEM 236 – Spring 2010 Exam III 7 6. [15 points] Propose a complete synthesis of the target molecule within the given constraints: CHEM 236 – Spring 2010 Exam III 8...
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