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mar_03 - The following reaction sequence would be a good...

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3/3/2010 1 The following reaction sequence would be a good synthesis of α -bisabolene. OH O A. Very sure this is true B. Somewhat sure this is true C. Maybe this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false α -bisabolene Which is the bad step? A B C D OH O α -bisabolene Is there a better synthesis? O P Ph Ph Ph O α -bisabolene How are Wittig reagents prepared? O P Ph Ph Ph O α -bisabolene Which of the following reactions would you predict to be faster? O Ph 3 P CH 2 Ph 3 P CH 2 A O O CH 3 Ph 3 P CH OCH 3 O C Ph 3 P CH OCH 3 O C O Ph 3 P CH OCH 3 O C B Are α , β -unsaturated esters useful? O H OH O O CH 3 Ph 3 P CH OCH 3 O C O 1. H-Al(i-butyl) 2 2. H 3 O 1. LiAlH 4 2. H 3 O very, very slow
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3/3/2010 2 Why do the phosphonate anions react faster? O P CH OCH 3 O C O CH 3 O O O CH 3 Ph 3 P CH OCH 3 O C O very, very slow O CH 3 OCH 3 O fast How are phosphonate anions prepared? O P CH OCH 3 O C O CH 3 O O O CH 3 Ph 3 P CH OCH 3 O C O very, very slow O CH 3 OCH 3 O fast N N O GLY O H SER O H N N O GLY O H SER O H
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