chm 2120 answers 2

chm 2120 answers 2 - Answers : Assignment #2/ 2009 T. Durst...

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Answers : Assignment #2/ 2009 T. Durst 1. O-SO 2 CH 3 H 3 C CH 3 CH 2 - S (-) Na (+) a) b) H 3 C CH 3 Br (-) OCH 3 H 3 C CH 3 Br c) K(+) (-) O CH 3 CH 3 H 3 C Br K(+) (-) O CH 3 CH 3 CH 3 CH 3 OH OH d) e) H (+) : H 3 C CH 3 O (+) OH H H H 3 C CH 3 O (+) .. H O H H 3 C CH 3 (+) O H 3 C CH 3 O H H 3 C Br O (-) O H 3 C H CH 3 H 3 C CH 3 H 3 C CH 3 OCH 3 + NaBr + NaBr + t-butanol CH 3 S-CH 3 -CH 3 + CH 3 SO 3 (-) Na (+) . CH 3 Br f) CH 3 Br or Br Br trans addition CH 3 OH g) Markownikov addition h) O intramolecular trapping of the more stable carbocation i) O epoxidation cis addition, retention of configuration 2.a) The reagent adds preferentially from the bottom, less hindered side to give the OH and the original isopropyl group on the same side. b) The highly hindered base preferentially attacks a beta hydrogen on the methyl group giving a beta elimination [E2] since these three are more accessible than the beta hydrogen on the carbon #3.
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Other possible alkenes CH 3 CH 3 CH 3 CH 3 c) Epoxide formation followed by opening of the epoxide to give the trans
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This note was uploaded on 01/10/2012 for the course CHM CHM 2120 taught by Professor Alysonflynn during the Spring '11 term at Carleton CA.

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chm 2120 answers 2 - Answers : Assignment #2/ 2009 T. Durst...

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