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Exam 3 -- Spring 2006 -- Blank

Exam 3 -- Spring 2006 -- Blank - I(28 points Name Page 1...

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Name _______________________ Page 1 I. (28 points) Complete the following reactions as directed. Trans formations requiring seque ntial experimental steps should be numbered appropriately. Show the major organic product(s) unless otherwise specified. Abbreviations for reagents are n’t allowed. If a product forms as a stereoisomeric mixture, draw one and write "+enantiomer" or "+diastereomer" in the box. C C CH 3 C C CH 3 H H OH C C H + Na Br + H 2 4 only thisproduct continues 4 4 4 C H 3 C H 3 C H 3 C O K A. B. C. 4 4 HO OH H 2 Pd/C O O O H CH 2 CH 3 Ph H 1) O 3 2) H 2 O 2 O CH 2 CH 3 Ph H CH 2 Ph only this alkene product! 4
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C H H 3 C CH 3 Compound B Name _______________________ Page 2 II. (24 points) Compound B undergoes bimolecular elimin ation when treated with NaO 2 CH 3 to form a single, major product. i) Draw the curved arrow mechanism for this reac tion using the chair conformation that gives the fastest rate of elimination, and ii) Draw the elimination product (Product C). 8 i) curved arrow mechanism for reaction with NaOCH 2 CH 3 4 A. i) Compound D is a stereoisomer of Compound B. The rate of bimolecular elimation of Compound D to form Product C (above) is expected to be the same as faster than slower than ( circle one ) the rate of bimolecular elimation of Compound B to form Product C.
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