In c a s e s w h e re th e p r o d u c t is to b e s

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Unformatted text preview: s w h e re th e p r o d u c t is to b e s p e c if ie d , if m o r e th a n o n e s ig n if ic a n t p r o d u c t is e x p e c te d , p r o v id e m o re th a n o n e s tr u c tu re , a n d in d ic a te w h ic h o f th o s e is lik e ly to b e th e m a jo r p r o d u c t. W o r k - u p s te p s m a y b e n e c e s s a r y in s e v e ra l c a s e s ; th e r e a c ta n t b o x m a rk e d w ith d o u b le a s te r is k s ( * * ) w ill r e q u ire a s e r ie s o f a t le a s t tw o r e a c tio n s . ( 4 p o in ts e a c h ) H 2O / H 2S O a) CH CH 4 3 OH 3 OH O C b) H 2C N aB H C H c) CH=CH CH / C H 3C H 2O H or 1 ) L iA lH 4 2 ) H 3O + H 4 H 2C OH B r2 / H 2O 2 C H C C H 2B r H H H C (ra c e m ic ) O O C C O O H H C d) H 3C e) C CH H 3C (in e x c e s s ) B 2H 6 /THF H 3C CH 2 H 3C CH B 2 3 C H 2 (q u e s tio n 3 , c o n tin u e d ) * 1 *) H H 3C H 2C f) C C C H 2C H / P d -B a S O 4 -q u in o lin e 2 ) O sO 4 / H 2O 2 o r K M n O 4 2 C H 2C H H or 1 ) N a / N H 3 (l) 2) M C P B A / H 3O ** OH H 3 3 OH C H 2C H 3 + Br Br 1) N B S Br g) 2 ) B r2 / C C l4 ( m ix tu r e o f s e v e r a l d ia s te r e o m e r s ) C H C l3 / N a O H h) Cl or Cl C H C l3 / t- B u O CH CH i) 3 3 OH M CPBA / H 3O + OH H ( + its e n a n tio m e r) 4 . C o m p o u n d 'D ' h a s f o r m u l a C 7 H 1 2 . W h e n 'D ' w a s t r e a t e d w i t h h y d r o g e n g a s i n t h e p r e s e n c e o f a P t c a t a l y s t , i t r e a c t e d t o g i v e c o m p o u n d 'E ', i n t h e p r o c e s s u s i n g t w o m o l e s o f H 2 f o r e v e r y m o l e o f c o m p o u n d 'D ' i n i t i a l l y p r e s e n t . W h e n c o m p o u n d 'D ' w a s o z o n o l y z e d , u s i n g a n o x i d a t i v e w o r k - u p , o n l y t w o p r o d u c t s ( c o m p o u n d s 'F ' a n d 'G ') c o u l d b e i d e n t i f i e d a s p r o d u c t s ; t h e r e l a t i v e a m o u n t s o f 'F ' a n d 'G ' w e re n o t d e te rm in e d . C o m p o u n d 'F ' w a s f o u n d t o b e t h e s a m e m a t e r ia l f o r m e d w h e n c y c l o p...
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This note was uploaded on 03/16/2013 for the course CHEM 212 taught by Professor Trzupek during the Winter '12 term at University of Illinois, Urbana Champaign.

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