0243Pb51an-09.cwk (WP)

0243Pb51an-09.cwk (WP) - possible chair forms OTs H CH 3 H...

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Answers to Problem 51, Chemistry 0243 - 2009 First, make a good three-dimensional drawing, keeping the large tert -butyl group equatorial. Only the hydrogens (not the deuteriums) are in position to take part in a 180° anti E2 reaction, thus leaving two deuteriums still in the molecule. (CH 3 ) 3 C Br D H C(CH 3 ) 3 D D base E2 H D H CH 3 CH 3 The two compounds must share cis and trans structures. There is no way to do this problem without making good, three-dimensional drawings of the compounds. Here they are in both
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Unformatted text preview: possible chair forms: OTs H CH 3 H OTs H H CH 3 OTs H H H 3 C H H H H OTs H H 3 C H H H H H 2 1 Only the hydrogens labelled with the arrows are in position to do a perfect, 180° anti elimination, and so the compound assigned as 1 gives only the single product shown, whereas 2 gives two products. OTs H CH 3 H OTs H H CH 3 H H H H CH 3 CH 3 CH 3 + loss of H b loss of H a b a 1 2...
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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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