ProblemSet10 - CHEM 3570, FALL 2008 Problem Set 10 Some NMR...

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CHEM 3570, FALL 2008 Problem Set 10 Some NMR problems……. . 1) Draw the structure of the products ( A-D ) in the empty boxes provided using the spectroscopic clues provided. The Wacker and IBX reactions are commonly used chemical transformations in organic chemistry. We did not discuss these reactions in class. By solving this problem you will learn about these reactions for the first time . Starting Material Wacker Reaction A 1) MeMgBr 2) H 3 O + B IBX C 1) MeMgBr 2) H 3 O + D Spectroscopic and Chemical CLUES: Data for A: Proton NMR : 2.45 (t), 2.09 (s), 1.61 (m), 0.96 (t) Data for B: Proton NMR : 5.20 (t), 2.09 (m), 2.05 (s), 2.00 (s), 1.06 (t) Data for C: Proton NMR : 6.60 (m), 6.12 (d), 2.25 (s), 1.94 (d) Data for D: Proton NMR : 6.10 (d), 5.90 (m), 5.60 (d), 5.65 (d), 1.95 (d), 1.90 (s) Chemical clue : This reaction Self-dimerizes when heated!!!! Suggest CHEM359 conditions (Reagents) for the formation of A and C from the starting material provided.
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2) a) When acetone is treated with NaH it produces Compound A which has
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ProblemSet10 - CHEM 3570, FALL 2008 Problem Set 10 Some NMR...

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