IN Class problem wittig rea_F07

IN Class problem wittig rea_F07 - In Class Problem...

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Unformatted text preview: In Class Problem Synthesize the following compounds using a Wittig reaction in one of the steps. You can use any organic or inorganic reagents necessary, but all sources of carbons should come from alcohols containing four or fewer carbons, or benzene. H H Retrosynthesis + PPh3 H H H + O H Br OH Br Synthesis Br + PPh3 Br Br2 FeBr3 H2/Pt 1000 oC 100 psi H 1) PPh3 2)n-BuLi - OH PCC O H + PPh3 H H + O + OPPh3 H H R e tr o s y n th e s is : o p tio n 1 O + P h3P _ O H C l o p tio n 2 _ PPh 3 H O + O H Br H O O H S y n th e s is : o p tio n 1 O H C rO 3 O H O S O C l2 p y rid in e C l 1. PPh3 2 . n -B u L i P h3P _ Ph3P _ + O o p tio n 2 y o u s h o u ld b e a b le to fig u re o u t. S a m e re a c tio n s , d iffe re n t c o m p o u n d s . R e tr o s y n th e s is : n o te th a t th is k e to n e h a s 5 c a rb o n s . T h e re fo re I n e e d to d o a n o t h e r c a r b o n - c a r b o n b o n d f o r m i n g r e a c t i o n t o m a k e i t . I d o n 't k n o w h o w to fo rm a C -C b o n d a n d a k e to n e s im u lta n e o u s ly , s o I n e e d to c h a n g e th e fu n c tio n a l g ro u p . O + Ph3P _ Br w h y a n a lc o h o l? B e c a u s e I k n o w h o w to m a k e a k e to n e fro m a n a lc o h o l e a s ily , a n d I k n o w th a t I c a n m a k e a C -C b o n d a n d a n a lc o h o l s im u lta n e o u s ly b y a g rig n a rd re a c tio n . O H O M gBr + H Br H O H O H S y n th e s is : P B r3 M g E t2O C rO 3 p y rid in e O H Br M gBr + O H H O H 1 . E t2O 2 . H 3O + O H C rO 3 O + 1. PPh3 2 . n -B u L i (fro m a b o v e ) Br Ph3P _ ...
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This homework help was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Chahoua during the Fall '07 term at Wake Forest.

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