Trzupek Practice Exam 3 Key

Trzupek Practice Exam 3 Key - 1 . P r o v id e s tr u c tu...

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Unformatted text preview: 1 . P r o v id e s tr u c tu r e s o r n a m e s , a s n e e d e d , fo r e a c h o f th e c o m p o u n d s s h o w n b e lo w . D o a n y fiv e o f th e s ix ; b e s u r e to C R O S S O U T th e o n e y o u w is h to s k ip . (3 p ts e a c h ) HO C a. CH 3 C b . _ _ _ _ _ _ _ _ 1 -_ m _e _t h_ y l_ c_y _c _l o_ p _ n _ a_ n_ o_ l_ _ _ _ _ _ _ _ __ _ _e_t d ic y c lo b u ty l a c e ty le n e Cl Cl H C H 3 -C H 2 -O C H 2-C H 2-O -H O H c. d . _ _ _ _ _ _ _ _ _ _ _ _2 _- _e t_ h_ o_ x_ y_ e_ t _h _a _n _ o_ l _ _ _ _ _ _ _ _ _ _ c is -2 ,4 - d ic h lo r o o x e t a n e CH3 C H -C H O H 3C H 3C C C CH C H 3 -C H 2 -C H 3 C H 2 -C H 2 -C H 2 -C H 3 2 H C 3 C C H 2 -C H 2 -C H 2-C H 3 ( d is r e g a r d R /S d e s ig n a t io n ) 2 - b u t y l-2 ,3 ,3 - t r im e t h y lo x ir a n e or r _e e . _ _ _ _ 2_ -_ ( _1 _- b _u _t y_ l_) _- 2_ ,_3 _, 3_ -_t _r i_ m_ _e _t h_ y_ l_o _x _i _ a_ n _ _ _ _ _ (Z )-5 -is o p r o p y l-4 -n o n e n e or f . _ _ _ _ _( Z _) -_ 5_ - _( 2 -_ p_ r_ o_ p_ y_ l_) n _o _n _- 4_ -_ e_n_ e_ _ _ _ _ _ _ _ _ _ _ _ 2 . F o r e a c h o f th e f o llo w in g r e a c tio n s , p r o v id e th e m is s in g p r o d u c t o r r e a g e n t, a s r e q u ir e d . I f s e v e r a l p r o d u c t s a r e lik e ly , g iv e th e s tr u c t u r e o f t h e m a jo r o n e (s ); if n o r e a c tio n is e x p e c t e d , w r it e N R . ( N o t e : s o m e c o n v e r s io n s m a y r e q u ir e m o r e th a n o n e r e a c tio n ). D o a n y 1 2 o f th e 1 3 s h o w n ; c le a r ly c r o s s o u t 1 . (5 p ts e a c h ) a. C H 3-C H 2 C C H 3C C H 2-C H H 2O / H 2S O 3 C H 2C H 4 H 3C C H 3 C H 2C H 2C H OH 3 (ra c e m ic ) O 1) b. C H 3 -C H 2 -C H c. C 2 H 3C S Cl , p y r id in e O OH 2 ) K I, a c e to n e C H -C H 2-C H 3 O C H 3 -C H 2-C H O 2 S CH O Br N B S (w ith p e r o x id e s ) C C H -C H -C H 3 (ra c e m ic ) OH d. C H 3 -C H 2 C H C H 2-C H H 2S O 4 /∆ H 3C H C 3 H M CPBA e. C H 3 -C H 2-C H 2-C H CH 2 (o r o th e r p e r o x y c a r b o x y lic a c id s ) C H 2C H O H C H 3 -C H 2 -C H 2 (+ c is ) C H H 3 (+ e n a n t io m e r ) H B r 2 / C C l4 Br (ra c e m ic ) f. Br H 3 (q u e s t io n 2 , c o n tin u e d ) C rO g. H O -C H 2C H 2C H h. H C (H 3C )3C H 3C i. j. CH H 3C C H 2C H 2C H 2-O H 2 CH 2 C CH H H 2O / H 2S O 4 / H gSO 4 3 3 3 H -C l / Z n C l2 O C H C (H 3 C )3C e th a n o l so lv e n t C C H 2 -C H 2 -C H 2-C H OH O / H C l / p y r id in e C H 3C H 2-S - N a + O C 3 C H 2-C H 2-C H 2 -C H C 2 H OH H 3C CH S O C CH H 3C 2 C H 2C H C H 2 -C H 3 3 3 C C H 2 -C H 2 -C H 2-C H Cl 3 OH CH 3 k. 2 ) H 3O CH l. C H 3-C H 2-C H CH 1) M C PB A CH + OH 3 CH O C O - N a+ C H 3C H 2O / C H 3C H 2O H 3 (ra c e m ic ) O C H 3-C H 2-C H CH H 2 3 C O - Na+ O Br H CH m. H CH 3 1) O 3 / -7 8 o 2 ) (C H 3)2 S H O C 3 H C CH H 3 CH 3 3 . a I n p p e r a o c p h r o i a f t t e h e s t s r e u r c i t e u s r o e f s . c o ( m 4 p p o o i u n n t d s s e a g c i v h e n 4 b 0 e p l o t w s f , o p r i c t k h e o u p t a g a e n ) d m a r k ( a s r e q u e s t e d ) t h e a . b C e i r t c h l e e w t h e e a c k o e m s t . p o u n d w h i c h w o u l d b e t h e s t r o n g e s t b a s e ; c r o s s o u t t h e o n e w h i c h w o u l d C H 3 C C C H 3 C H 2 N H C H 3 C H 2 O C H 3 O C O b . t I h n e a c n o m e l i p m o i u n n a d t i w o n e w w i o t u h l d t h e e x a p l e k c y t l a h c a c l o i d r e d i o n n g t t h o e S r a i y g t h s t e , f c f ' i s r c R l e u t l e h e t o C H 3 C H 2 C H 3 C H C H 3 d b i e c f t o o r H f m 3 b C e e d l o i n w C e t h s H t e 3 i h n i g y h i e e l s d t . y i e l d ; c r o s H s o u t t C h H e 3 o n e i t w o u l d p r e C H 2 B r H 3 C C H 3 C H 3 c . C i r c l e t H h C e c o C m C H p ( o C u H n 3 d ) 2 i n w h i c h t h H e 3 u C n C d e C r l C i n H e ( C d H h 3 y ) 2 d r o g e n C h H a 3 s C t H h 2 e h C i g C h H e s ( C t H b o 3 ) n 2 d d i s s o c i C H 3 C H 2 C C C H 3 a t i o n e C n e H r 3 y C ( H B 3 D E ) ; c r o s s o u t t h e o C n H e 3 i C n H w 3 h i c h t h e u n d e r l i n e C d H H 3 C h H a s 3 l o w e s t B D E . C H 3 C H 3 H C H C C H 2 C H 3 H C H C C H 2 C H 3 H C H C C H 2 C H 3 H C H C C H 2 C H 3 d . t C h i e r c o l n e e t h w e h c i c C o h m F 3 w p o o u n l d d b b e e e l o x w p e w c t h e i d c h t o w h o a C u v l F e d 3 t b h e e e l x o p w e e c s t t e p d K t o a . h a v e t h C e H h 3 i g h e s t p K a ; c r o s s o u t C H 3 C F 3 C H 2 C H 3 O H C H 3 C H 2 C F 3 O H C B r 3 C H 2 C H 3 O H C F 3 C H 2 C H 3 O H e . C a l i k r e c n l e e ; t h c e r o c s o s m o p u o t u t h n e d o b n e e l o w w h w i c h h i c w h o w u l o d u r l d e a r c e t a l c e t a m s t o r s e t a r d e i a l y d i l y w i t h h o t H 2 S O 4 t o g i v e a n H O C H 2 C H 2 C H 2 C H 3 C C H H 3 C H C H C H 3 C H C H 3 C O H H C H 2 C H 3 C H 3 C H 3 3 2 O H 3 C H 3 C H 2 C H 2 O C H C H 3 4 . P r o p o s e a s t e p -b y -s t e p s y n t h e s is o f o n e o f t h e t w o c o m p o u n d s b e lo w , b e g in n in g w i th th e in d ic a te d s ta r t in g m a te r ia l. Y o u m a y u s e a s w e ll a n y a p p r o p r ia te r e a g e n ts a n d s o lv e n ts , a s w e ll a s a n y o n e -c a r b o n o r g a n ic c o m p o u n d s . R e m e m b e r - in m o s t c a s e s , y o u a r e b e s t o ff w o r k in g b a c k w a r d s . (1 2 p ts ) CH2 H 3C C H C ; fr o m C H 2C H 2C H 3 H C H 3-C (y o u m a y u se th e p r o p y n e a s o fte n a s n e e d e d ) C -H O -C H 3 C H 3-O ; fr o m H H 1st seq u en ce: H 3C C C H 2 / B aSO 4 q u in o lin e or N a / N H 3 (l) H H 3C C C H C H 2I2 [fir st p r o d u c t] Zn - Cu H 3C N aN H H 3C C H 2 CH2 H 3C H -B r (p e r o x id e s) C C H 2C H 2C H 3 C H 2n d sequ en ce: C H 2 / B aSO q u in o lin e C H H 3C C O -C H 3 H C H 3C H 2O hν H 4 Br B r2 C H 3-O C H 3C H 2C H 2 B r C H 3C H 2O H 1) N aH 2 ) C H 3-B r HO H OH H O sO 4 / H 2O 2 C C H 2 -C H 2-C H 3 5. R e a c t io n o f H - B r w i t h 1 - b u t e n e i n a s o l v e n t s u c h a s c h l o r o f o r m o r c a r b o n t e t r a c h l o r i d e g iv e s a s a p r o d u c t c o m p o u n d 'A ', w it h f o r m u la C 4 H 9 B r . H o w e v e r , w h e n t h a t r e a c t io n is c a r r i e d o u t u s in g m e t h a n o l a s a s o lv e n t , a n o t h e r p r o d u c t b e s id e s c o m p o u n d ' A ' is fo r m e d . T h is s e c o n d p r o d u c t , c o m p o u n d 'B ', is n o t o x i d iz e d b y C r O 3 / H 2 S O 4 , n o r d o e s it r e a c t w ith B r 2 /C C l4 . G iv e t h e s t u c t u r e s o f 'A ' a n d 'B ', a n d p r o v i d e a s t e p - b y - s t e p m e c h a n is m f o r t h e f o r m a tio n o f b o th 'A ' a n d 'B '. H H 'A ' = H 3C C C H 2C H 3 'B ' = H 3C C C H 2C H 3 O -C H 3 Br m e c h a n ism s: OR Br H H O CH3 O CH3 Br H H 2C C C H 2 -C H 3 H H H 2 C C C H 2 -C H 3 H H O CH3 H O CH3 Br H 3C C C H 2 C H 3 H 3C C C H 2C H 3 H H O -C H 3 H 3C C C H 2C H 3 H 6. C o m p o u n d 'C ' is a n a lk y n e o f f o r m u la C 8 H 1 4 . R e d u c tio n o f 'C ' in a s p e c if ic fa s h io n g iv e s c o m p o u n d 'D '. I f c o m p o u n d 'D ' is a d d e d t o a s a m p le o f B r 2 in C C l4 , th a t s a m p le s lo s e s it s r e d - b r o w n c o lo r . T r e a t m e n t o f 'D ' w it h o z o n e , f o llo w e d b y a w o r k -u p w ith z in c in w a te r g iv e s o n ly o n e p r o d u c t, c o m p o u n d 'E '. C o m p o u n d 'E ' is th e s a m e m a t e r ia l w h ic h is f o r m e d b y r e a c t in g 1 - b u t a n o l w it h p y r id in iu m c h lo r o c h r o m a t e , w h ic h o x id iz e s a lc o h o l c a r b o n s t o c a r b o n y l g r o u p s . R e a c t io n o f c o m p o u n d 'D ' w it h O s O 4 g iv e s c o m p o u n d 'F '; c o m p o u n d 'F ' is f o r m e d a s a p a ir o f e n a n t io m e r s . P r o v id e th e s tr u c t u r e s fo r c o m p o u n d s 'C ', 'D ', 'E ', a n d 'F ' ( b e s u r e to g e t a n y s t e r e o c h e m is tr y c o r r e c t) , A N D p r o v id e th e r e a c t io n u s e d t o c o n v e r t 'C ' to 'D '. 'F ' = C H 3C H 2C H 2 H H OH OH ( + e n a n tio m e r) C H 2C H 2C H 3 O 'E ' = H 'D ' = C H 3C H 2C H 2 C H 'C ' = C C H 2C H 2C H 3 H C C H 2C H 2C H 3 C H 3C H 2C H 2 C C C H 2C H 2C H 3 N a / N H 3 (l) C H 3C H 2C H 2 C H H = 'D ' C C H 2C H 2C H 3 ...
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This note was uploaded on 02/28/2012 for the course CHEM 210-1 taught by Professor Trzupek during the Fall '08 term at Northwestern.

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