chem236-2009fa-hex3-key - Fall 2009 Chemistry 236 Hour Exam...

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Chemistry 236 Hour Exam 3 Fall 2009 Last Name _______________________________ First Name _______________________________ 1. _______ 15 pts 2. _______ 12 pts 3. _______ 30 pts 4. _______ 28 pts 5. _______ 15 pts Total: __________ 100 pts KEY ANSWER 15 12 30 28 15 100
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1. (15 pts) Mechanism. Give a structure for intermediate A and a mechanism for the formation of A and B . Is the stereochemistry of B the one that would be obtained from your mechanism? Explain. 2 A B [CH 3 (CH 2 ) 3 ]CuLi O CH 3 (CH 2 ) 4 H CH 2 OH H O H O H O H O H CuLi 2 O - H O H A O CH 3 (CH 2 ) 4 H CH 2 O - H H 3 O + Yes, the stereochemistry is correct. The first step does not effect the stereocenter of the epoxide - the reaction is at the methylene group. So this center remains the same. The second step is a nucleophilic substitution - an opening of the epoxide which goes with inversion at the more substituted carbon of the second epoxide.
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c. An alkane would exhibit the following (m/z) mass series in EI MS:
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This note was uploaded on 11/07/2011 for the course CHEM 236 taught by Professor Silverman during the Fall '08 term at University of Illinois, Urbana Champaign.

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chem236-2009fa-hex3-key - Fall 2009 Chemistry 236 Hour Exam...

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