Trzupek Exam 3 Key

Trzupek Exam 3 Key - 1 . C o n s id e r th e th re e a lk y...

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Unformatted text preview: 1 . C o n s id e r th e th re e a lk y n e s s h o w n b e lo w : CH 2 C C CH 3 = 'A ' CH C CH 2 C 2 C H C C H 2-C H 3 = 'B ' = 'C ' a ) C i r c l e t h e c a r b o n h o l d i n g t h e m o s t a c i d i c h y d r o g e n i n a l k y n e 'C '. ( 3 p o i n t s ) b ) C i r c l e t h e c a r b o n h o l d i n g t h e m o s t a c i d i c h y d r o g e n i n a l k y n e 'A '. ( 2 p o i n t s ) c ) P r o v i d e t h e I U P A C n a m e f o r a l k y n e 'C '. ( 2 p o i n t s ) 4 -p h e n y l-1 -b u ty n e d ) W h i c h o f t h e s e a l k y n e s ( ' A ' , ' B ' , o r ' C ' ) w o u l d b e t h e m o s t s t a b l e ? ( 2 p o i n t s ) _ _ _ _ _' B_ _' _ _ _ _ _ _ e ) W h i c h o f t h e s e a l k y n e s w o u l d b e t h e l e a s t s t a b l e ? ( 2 p o i n t s ) _ _ _ _ '_C _ ' _ _ _ _ _ _ _ f ) P r o v i d e b e l o w t h e s t r u c t u r e o f t h e p r o d u c t e x p e c t e d i f a l k y n e 'C ' w a s f i r s t t r e a t e d w i t h ( s i a ) 2 B H , fo llo w e d b y a w o rk -u p w ith b a s ic h y d ro g e n p e ro x id e . (2 p o in ts ) O C H 2 -C H 2 -C H 2 C H 2 . a ) P ro v id e b e lo w th e s tru c tu re o f a lly l a lc o h o l (4 p o in ts ) H 2C = C H -C H 2-O -H b ) P ro v id e th e IU P A C n a m e fo r th e a lk e n o l y o u s p e c ifie d in a n s w e r 2 a ) a b o v e (5 p o in ts ) 2 -p ro p e n -1 -o l or p ro p -2 -e n -1 -o l c ) C o u ld y o u r c o m p o u n d in a n s w e r 2 a ) b e p r e p a r e d b y a r e a c tio n in v o lv in g a G r ig n a r d r e a g e n t? I f s o , s h o w th e r e a c ta n ts r e q u ir e d ; if n o t, e x p la in w h y n o t. ( 5 p o in ts ) y es; H 2C = C H -M g -B r 1) H 2C = O 2) H 3O + 3 . P r o v id e s tr u c tu re s f o r th e m is s in g p r o d u c ts o r r e a g e n ts , a s r e q u ir e d - if n o re a c tio n is e x p e c te d , w rite " N R " ( n o te - " N R " is n o t a n a c c e p ta b le a n s w e r f o r a r e a g e n t - if a s ta r tin g c o m p o u n d a n d a p r o d u c t a r e g iv e n , y o u m a y a s s u m e th e r e is s o m e re a g e n t w h ic h w ill e f f e c t th e d e s ir e d c o n v e r s io n ). In c a s e 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 e n t e n e i s o x id a t i v e l y c le a v e d u s in g w a r m , b a s ic p e r m a n g a n a te ( M n O 4 ) , a s s u m in g s u b s e q u e n t n e u tr a liz a tio n w ith a q u e o u s a c id . a ) P r o v i d e s t r u c t u r e s f o r c o m p o u n d s 'D ', 'E ', 'F ', a n d 'G ' ( 9 p o i n t s t o t a l ) 'D ' H 2C = C H -C H 2-C H 2-C H 2-C H = C H 'E ' C H 3 -C H 2-C H 2-C H 2-C H 2 -C H 2-C H 'F ' H O 2C -C H 2-C H 2-C H 2-C O 2H 'G ' H C O 2H 2 3 b ) In d ic a te th e re a g e n t(s ) n e e d e d fo r a n o x id a tiv e w o rk -u p in th e o z o n o ly s is p ro c e d u re . ( 3 p o in ts ) H 2O 2 c ) C o m p o u n d 'X ', a n i s o m e r o f 'D ', w a s f o u n d t o r e a c t w i t h o n l y o n e m o l e o f H 2 p e r m o l e o f 'X , w h e n t r e a t e d w i t h H 2 a n d P t . W h a t s t r u c t u r a l f e a t u r e i s p r e s e n t i n c o m p o u n d 'X ' w h i c h i s N O T p r e s e n t i n c o m p o u n d 'D '? ( 3 p o i n t s ) . 'X ' m u s t p o s s e s s a r i n g i n i t s s t r u c t u r e 5 . W h e n c o m p o u n d 'H ' ( s h o w n b e l o w ) w a s t r e a t e d w i t h a s o l u t i o n o f m o l e c u l a r i o d i n e , i n t h e p r e s e n c e o f a w e a k b a s e l i k e b i c a r b o n a t e i o n , p r o d u c t 'Z ' w a s f o r m e d . a ) P ro v id e a s te p - b y -s te p m e c h a n is m fo r th is p ro c e s s ; b e s u re to in c lu d e a n y a n d a ll in te rm e d ia te s th a t a re lik e ly to o c c u r to a n y s ig n ific a n t e x te n t. (8 p o in ts ) O I2 / H C O I 3 ( = 'Z ') O OH ( c o m p o u n d 'H ') HCO O 3 O I2 O I O I O O I O O = I O I I O O O O b ) A c y c l i c e s t e r g r o u p ( s u c h a s t h a t f o u n d a s p a r t o f t h e s t r u c t u r e o f c o m p o u n d 'Z ') i s c a l l e d a " l a c t o n e " g r o u p . P r o v i d e t h e s t r u c t u r e o f a l a c t o n e i s o m e r o f 'Z ', w h i c h c o u l d a t l e a s t b e h y p o th e tic a lly c o n s id e re d a s a p o s s ib le p ro d u c t in th e tra n s fo rm a tio n a b o v e . ( 2 p o in ts ) I O (q u e s tio n d ro p p e d d u e to a m b ig u ity ) O (re s u lt o f a tta c k a t le s s -c ro w d e d c a rb o n o f " io d in iu m io n " in te rm e d ia te ) 6 . S ta r tin g w ith e th y n e a n d /o r p ro p y n e ( y o u c a n u s e e ith e r a s m a n y tim e s a s y o u w a n t) a s y o u r o n ly s o u rc e s o f c a r b o n , a n d u s in g a n y re a g e n ts a n d s o lv e n ts y o u w is h , p ro p o s e s y n th e tic s c h e m e s fo r O N E o f th e tw o c o m p o u n d s b e lo w : OH F o r F U L L C R E D IT (1 2 p o in ts ) : H H 3C H H F o r H A L F C R E D IT (6 p o in ts ): H FU LL: H 3C C H 2 / Pd - B aSO q u in o lin e CH 4 C H 3-C H = C H H C C N aN H H O H 3C H -B r (p e ro x id e s ) 2 2 H H 2O / H 2S O C C H 2-C H 2-C H C CH N aN H 2 H 3 O H 3C 4 H C C CH C C C H 3C 3 H 3O C + OH C CH H 3C 2 / Pd - B aSO q u in o lin e 4 C H 3 H C 3 3 3 C H 2-C H 2 -C H C C C H 2-C H 2-C H 4 OH C H 2-C H 2 -C H C CH C 3 H gSO C C H 3-C H 2-C H 2-B r C H 2 -C H 2 -C H C C CH 3 H 3 H A LF: Na H C C H NH 3 (l) H 2C = C H H -B r C H 3-C H 2-B r 2 H C H 3 -C H C H 2 C H C N aN H 3 Na C CH CH 3 N H 3 (l) 2 C C C H 3-C H CH 2 C 3 C CH 3 3 ...
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