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Exam 3 -- Winter 2008 -- blank

Exam 3 -- Winter 2008 -- blank - I(30 points Name Page 1...

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Name _______________________ Page 1 w08.ex3.p1 I. (30 points) Complete the following reactions as directed. Transformations requiring sequential 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. B. KMnO 4 A. 1. O 3 (excess) 2. Zn Draw the optically active compound that is produced in each of these reactions. 13 C-NMR signals: 3 When Compound Y is treated with either of the following reagents only a stereoisomeric mixture of products results. Draw a l l of the stereoisomeric products for each reaction. H 2 (gas) Pt Compound Y CH 3 OH H 2 SO 4 (cat.) c) Provide the IUPAC name, including stereochemistry when needed, for Compound Y. 4 4 (a) (b) 4 (a) H H H 2 Pd/CaCO 3 PbO (b) (ii) Draw ALL the organic products that fit the NMR criteria in each space, and specify the number of each if more than one forms. 13 C-NMR signals: 2 3 2 2 3 (i) (c) OH 1) NaOCH 3 2) CH 3 I 2) CH 3 ONa only this stereoisomer 4 1) CH 3 S O O Cl N 4
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Name _______________________ Page 2 w08.ex3.p2 II. (26 points) When 1 equivalent of bromine is added to 1,3-butadiene, Compound B is the product formed in the greatest amount, even though a different stereoisomeric mixture of products (each with formula C 4 H 6 Br 2 ) is predicted to form. Draw in the missing products, use all the information provided .
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