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midterm2key - \ «"1. IV \\ //, f ,1 \g 4 / ,2 / /...

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Unformatted text preview: \ «"1. IV \\ //, f ,1 \g 4 / ,2 / / / » / Chem 118 C (y / Summer Session I / 2008 " Second Midterm July 22, 2008 Instructor : Nambiar This exam contains seven pages and six problems. Please make sure that your copy contains all the seven pages. If there is a problem, please let us know before you start answering. Please answer all questions. Name: Last First MI I. D. # TA / Section: Problem # Points I = l. (40 pts). Draw the structure of the expected organic product (5) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction". CH3Li T (CH3CO)20 (1 eq)/ A [C3 C3 ‘ YE]; ‘ _ ,> (5K \ l) CH3NH2 2) (CH3)2CHNH——-< >——OH . l. ‘ .,H g: 3) CH3«@——NH2 1. NaNOg / HCl / 00C [,1 ha .7 ,, u C *5 {9} (ON 2. CuCN / 50°C 1.CHI __ #31: Mil/(a3 4" OMB 3 ("is “C” M" I”; 73a: 2. AgzO/HgO/A cl KMnO4/KOH/A .~ ‘ ’~ ‘ 5&6 W» 5 o v CH<CH3>2 CM)" A /H+ ‘ Jr 6) CH3CH=CH—CO-CH2CH=CHCH3 C: ht afifl /C° H’C . {TM 1. Br2 / hv My”? 55‘“ 7) CH3 —@—CH2CH2CH3 s 2. NaOC2H5 /A » 3iéHOPI/H+/A w “H .t a 2 5 (5 § w 9‘ ‘ , 9") S S 1. n-BuLi (1 equivalent) ‘1‘ C {{;’(”€§":Zf§€#t3 _,____. r ,,. {L O ,z: ‘ _ \ HQOH 2. C6H5COC1 & 3.HgC12,Hg0/1—120/A (a Z) / 1. chm fieéflg page?“ 10) CH3CH(COOCH3)2 M- I —-O K "’U 2. CH2=CH~CO—CH3 / / W 3h ’ ,f é 2 2/» I - I ,. Ha (10 pts) Show detailed reaction mechanisms for the following, reaction. NaBH3CN / CH3OH / H+ (Catalyst) OCH—CHQCHQC(=NH) CH2CH2CHO 4/ U) 11b (10 pts) Show detailed reaction mechanisms for the following. 1.02/A : : 2. H30+ ,‘ ~—é> r a ’y-z—flH /" ‘3 A 5—51.? ;\ / 5* p/ “r / ’f ./ / C9. / R l Nile/“"3 ,/ \ H 6—” 1% I 1e // RM 1 x ‘ {T 2;] Vii/6242f :5- Wfifi 1H. (21 pts). Show how you would carry out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed. if“ {‘97 it CH3O-—O——CHZOH a CH3O—O—NH-C2H5 ‘ .4: it; C’ y" w 5 '~ 7. IIK K K t Twé’ WM 1, "Ugh" ‘ M to f. ’i QC, “ Rf / CC/3\ a 7 r War I x “a r .r x _, ,x\ I»; z a» 1,1 . r’ . 4r "‘ w)? L ‘”\L’WyL/Zj:5 0% W 9\ f“; Lg‘é‘ ck (:3— 1\!IH2 9C2H5 _. —————“' ‘ CHZCH2CH3 WW 3-3, 14ml . 0. g i Ell/\‘Qfl/ 5 IV. (15 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 1. Q5115 co NH—CH2CH(CH3)2 Neel-85% ’ g—U mu? / l ‘3’ r 2. CH3NH 402 W‘KW%f ’ [Wt/Web" wfl'W,V*’L}\-‘ Q/ “(Pb W W» (WsLM/m 3°6- Wuz at. a x ’2 ‘L " u ‘ 3. @CHz-CHz-N<C2Hs>2 (v/ (1/.«31W 02¢ % f/gfiwaawtx p—ec—(eéL/Cfigflé’é’ 4. o—Nitrophenyl 2—bromobutanoate /y \é YA - .3 a} 3‘ 5 CH3OCH2CH2<@—vCONH2 fl~(o?- 2°C) ‘1? , V. (8pts) Rank the following compounds in decreasing order of basicity. H OH ONa OH NH2 NH2 6 (EONHz ; ! w ho © 05on F A B C D E F G H lligh Basicity Scale Low WT VI. (16 pts).Compound A (C11H14O3N2) gave the following proton NMR spectrum. IR spectrum showed strong absorptions at 1695 cm"1 and 1650 cm’l. Deduce the structure of compound A. What is the product you expect to get when compound A is heated with 6M HC] in water and LiA1H4 in separate reactions ?. -3 1-1' '3 H‘ , H <3 11 7 / x / f c) ’1 \IL / / 6MHC1/HO/A 0/1/ W‘yfl Afr \ Compound A 2 3’ t C? C / 5 LiA1H4 - e / CornpoundA W \ d /\V \1 ...
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midterm2key - \ «&amp;quot;1. IV \\ //, f ,1 \g 4 / ,2 / /...

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