Final Exam -- Spring 2006 -- Blank copy

Final Exam -- Spring 2006 -- Blank copy - I(38 points KEY...

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Name _______________________ Page 1 I. (38 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 not allowed. If a product forms as a stereoisomeric mixture, draw one and write "+enantiomer" or "+diastereomer" in the box. C 5 5 5 A. B. C. 5 5 1) O 3 2) H 2 O 2 C NO 2 5 C H 3 C H 2 AlCl 3 Cl C CH 3 O H 3 C H H D. CH 3 H 3 C C O O H O 8 CH 3 H CH 3 H 3 C CH 3 Pt KEY
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Page 2 II. (37 points) Complete the following multi-step reactions starting from the starting material in the center below. Be sure to number steps where required. If a mixture of stereoisomers results, draw one and write "+enantiomer" or "+diastereomer" in the box. If a mixture of structural isomers results, draw the predicted ma jor product. 5 A. B. 5 5 5 O OH O CN O CN 1. 2. NaSCH 2 CH 3 only this stereoisomer only this stereoisomer 1. NaH 2. CH 3 I The following reaction was recently reported ( Tetrahedron, 26, 62 62 5717). In the box below, show the mechanism of this reaction. Use H-B and B - for any Bronsted acids or bases, if needed. NOTE: Under certain conditions, alkoxy groups (like "OCH 3 ") can react with a Lewis acid to form a good leaving group. CH
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This note was uploaded on 02/18/2011 for the course CHEMISTRY 210 taught by Professor Nolta during the Winter '10 term at University of Michigan.

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Final Exam -- Spring 2006 -- Blank copy - I(38 points KEY...

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