0243Pb47-09.cwk (WP)

0243Pb47-09.cwk (WP) - If so, tell us which it is. e. Would...

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Problem 47, Chemistry 0243 - 2009 Reaction of the enantiomerically pure iodide 1 (C 8 H 9 I) with one molar equivalent of thiolate (HS ) ion in CH 2 Cl 2 , a slightly polar solvent, leads to enantiomerically pure 2 , C 8 H 10 S. H 3 C I H HS CH 2 Cl 2 C 8 H 9 I C 8 H 10 S 2 * (+)- 1 a. Draw the product and an arrow formalism for its formation. b. Is the starting iodide R or S ? c. Is the product or ? d. If the rotation of the iodide 1 is (+ = clockwise), as shown in the figure, can you tell if the product 2 will rotate the plane of plane polarized light clockwise (+) or counterclockwise (–)?
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Unformatted text preview: If so, tell us which it is. e. Would the reaction of 1 with thiolate be faster or slower in a nonpolar solvent? Explain carefully. f. Increasing solvent polarity in the reaction by adding methyl alcohol (CH 3 OH) leads to a decrease in the optical rotation of the product 2 . Why? g. What will happen to the rotation of 2 as we continue to increase the polarity of the solvent? Explain....
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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