KAHR exam1 - CHEM 337 SPRING 2006 EXAM 1 (ANSWERS)

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CHEM 337 SPRING 2006 EXAM 1 (ANSWERS) 1.____2._____3._____4._____5._____6._____7._____8._____9._____10._____11._____ TOTAL SCORE_________ Mistakes do get made when grading exams. The most common mistake is arithmetic. Check to see that your points add up to the total score awarded. If you have a more substantial question/concern please place these in writing with the entire exam attached in the mailbox of TA James Stewart. NAME_________________________________________________________ 1. Solomons 17.23a. (15 pts.) Write a reaction involving a lithium enolate for introduction of the methyl group the following compound (an intermediate in a synthesis by E.J. Corey [Paul Hopkins’s PhD advisor] of cafestol, an anti- flammatory agent found in coffee beans). Show the H-abstraction step explicitly. The answer book does not. O O O O O O O OLi CH 3 I LDA H :N(i-Pr) 2 Li + CH 3 -I
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2. (16 pts) Draw a mechanism that will account for the racemization of the starting ketone with the S configuration .
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(12 pts.) The mechanism for the following transformation has three intermediates. I have
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This test prep was uploaded on 04/15/2008 for the course CHEM 237 taught by Professor Andersen during the Fall '08 term at University of Washington.

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KAHR exam1 - CHEM 337 SPRING 2006 EXAM 1 (ANSWERS)

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