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E32005Key - E5 1 5705‘ K 67 l A molecule has to meet two...

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Unformatted text preview: E5 1 5705‘ K 67' l) A molecule has to meet two criteria to be considered chiral. Name them. 2 pts l l l, ,%'t Cu?) (71 .Aiélxc;-(“3/7L-*ro:g if); .Vk'jtbx . ’73ju‘L/VLL 2- ill; 0;; fruit: ij mam .1117 , f p I U 2) Butaclamol is a potent antipsychotic used in the treatment of schizophrenia. Although patients are given a racemic mixture of the drug only the (+) enantiomer has pharmacological activity. A) Draw the (—) enantiomer. 3 pts B) Draw a diasteoemer of Butaclamol 3 pts L" ‘-l /‘\ ~ J. ._ ., . . . , J.“ . ‘</ kA-Hafi) 3 * C'x \\ \ RAE the \ C‘\-\j»‘,-,‘. U; l’\ iLV‘x v“? 3 'IN . V \l ./ fi H ,4 i K \3“ . \ “as. (EARN-k H n?» /:"‘- wL/ (Auwvv ~..'\ \—~ / \‘/ \ l W \‘x / . xr 7' 7\}/ C \W h,- 1 . 2,57 ““ (Ll-'V‘KL“ —. L l/ h w ‘- L\ \f— C) How many different stereoisomers are possible for this Butaclamol? 3 pts )2 N 7: 223 "V 6/ N L [1- B’LL w<t7z< [ti/L; L341 "113“) 3) Look at the four molecules shown and answer the questions below. 15 pts H30 H30l HaC‘ ICH3 \CHa H30 CH3 III/CH3 A B C D A) Which is (are) meso? {A r; B C t D; B) Which is (are) achiral? {Al (B C ”\P C) Which can have a diasteroemer? :5 (B LC, ,7 KP D) Which is optically active? A B Li, D E) Which can have an enantiomer? A B C\ D 4) Determine the configuration(R,S) of each stereogenic center in Mevacor. Mevacor is a medication used to lower serum cholesterol. 3 pts each Circle One a (E S Neither _/ l ‘\ b R S either: C R (5‘ Neither d R S Neither 5) Look at the reaction below. Describe the stereochemical relationship between the two products of the reaction and subsequent optical activity for each product individually and as a mixture. CH3 Br—Br ——-> CCl4 (solvent) Relationship: 2 pts c:'\"!\c'~'¥l kJ‘J :2 VVLU“) Optical activity: 2 pts be EV» «Lox C7 LkN " , “‘7' \\ :ZA’C Lwl (unis '\ (W'Vw’i v '3 6) Draw 2(R)-chloro-3(S)—hydroxy—4E—heptene. 4 pts Cl 6|~§ 7) Provide all possible products from radical bromination. 8 pts 13:" Br—Br, hv i' / .. / / \//\\\z / ’f‘ \.’/fi. 8 r ' CCl4 (solvent) f i3 i" \“"/ A \'/‘\( ’ l I \ l 8) Provide the needed reagents. Be sure to include solvents! 3 pts each HO Cl H C l —————-—> P C" lav s ("lxl . _ OH Br P P i" 3 (vii) POl‘ \C- ’r P0 l0 l” 8' (i? l\} Br 7 ' .'> m- o c ~\ » fl VT J ) '1, 4K2"- \ E ,icg —————> .2) H2 C Br kc mg c a) act-ti“ ———-—————> “Hi F [cadet C7j3,2\C'l re. 9) Which of these compounds have the same oxidation level? 3 pts OH /\<(lD ‘8/ (CH) ---‘7 (cw) 0 +1 LCO’I Tl LCé) -—L,(CH) ”‘Yllg'fi‘l __ / H'“ -\< 1 QC”) “l; ZKL (j V — o _ * .__ < ...
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