Fall06FinalExamBlank

Fall06FinalExamBlank - I. (38 points) KEY Name _ Page 1...

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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 speci±ed. 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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Fall06FinalExamBlank - I. (38 points) KEY Name _ Page 1...

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