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Exam 3 -- Winter 2008 -- key

Exam 3 -- Winter 2008 -- key - ffiW\dbm&trw ry ffi*ffi Name...

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\dbm&trw ffiW ry. %ffi'*ffi + diastereomer (ii) Draw ALL the organic products that fit the NMR crileria in each space, and specify the number of eachif more than one forms. 1. Os (excess) + 2.Zn 1) NaOCH3 -..-+ 2) CHsl only this stereoisomer t. A. (30 points) Name Page 1 w08.ex3.pl 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. lf a product forms as a stereoisomeric mixture, draw one andwrite "+enantiomer" or "+diastereomer" in the box. (a) KMnO+ , H2 --..-+ Pd/CaC03 Pbo (c) Draw the optically active compound that is produced in each of these reactions. ""lro{7_Q 2)CH3ONa B. When Compound Y is treated with either of the following reagents only a stereoisomeric mixture of products results. Draw all of the stereoisomeric products for each reaction. 't ,"e^r. '',-q-- c) Provide the IUPAC name, including stereochemistry when needed, for Compound Y. H2 (gas) --+ Pt or5R (R)-1,5-dimethytcyclopent-1-ene could say Z too cHsoH -H2SOa (cat.) a) H. ,;t "$ q' Compound Y (b) lsc-NMR signals:3 ">-( / o H /" 13O-NMR signals:2 H -{ 'b 9CHs cH3oH only this needed Na oro ,"4,
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t ll. (26 Points) Bt2 . (1 equivalent) 1,3-butadiene question about its formation' Name Page 2 wo8'ex3.P2 Compound B (ii) The product(s) form(s) as: (check allthat aPPIY): l-la mixture of 2 diastereomers ll l-l" r"."tic mixture f-la singte optically active compound Fla sinste
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