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Fall 2002 KEY - I Final l 42points t-t n r f r[X oL Name...

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I Final t-t nr. -' €r",[X f oL l. (42points) Draw the structures of the missing products. If there is more than one possibleoutcome, provide the major product(s) as implied by any other information supplied. Show stereochemistry when known. 1. PPh3 2. CH3CH2CH2CH2LL Name KEI Page 1 CH=PPhr + LiBr + CH3CH2CH2CH3 (a) f", 'a Br (J. Med. Chem. 2002, 45, 3406) (b) HocH2\/,/o\,wocH3 \ l PhcHro-t- ...... -"ocH2Ph Br oYvo \J (NBS) CH2Br 'a Br CCla, hv (rn-= Q- = cuur) (c) o l l CH3CNH Q CH-COCHzCH, z. CrttCgt, * O= COCHzC H: (Bioorg. Med. Chem. 18tt.2002, 12,2635 HOCH2 F"'.. fr HOt',( F CHzCOCH: \ / n HO OH (e) o ^ o t' I cH? ii Z\4' tl I"'--. Fr-c-oH I ll N-o-cH2-c-o-c-cH3 'r" - \.,\f l^ dichloromethane \\ CH,I O (ors.Leu.2002,4,869) CH3CHISH (excess) HCI (cat.) (J. O rg. Chem. 2002, 67, 5142) o I I (l equiv.) cH3l\cH3 -.> H2SOa (cat.) HOCHr Fq I HOt,..( F CHzCOCH: H o-.,ro cHacH3 17 CnHzA Cl N OZ (ioniccompound) o tl cH3(cHre- cH - coH I ONH3 Cle + H2O Hzo HCI -l heat (d) C23 H32 Oa 52 draw as a Fischer projection H H H scHfH3)2 OCH2Ph OCH2Ph OH zoH o tl CH3CNH 9 l r l cH3(cH2)e- c- cocH2CH3 I O=COCHzC H:
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I Name KEY Page2 f. (44 points) A. As directed in the boxesbelow, provide a detailed, step-wise mechanism using the curved arrow notation for the following base-catalyzed transformation. t o r l l *Gcll., | i l " + \,Aon CornpoonO X Mechanism for conversion of Compound X to Compound Y : Ci'rl ,.-9b" 1z v-CH,: H -:---> v% "rO '3' -cHr -: -C-CH=C- ( Y 'cHr -s \A6n . A I O l t O ' ' - ri ^..I ^.. \"_q" 4 y.c-cH2-c-cH3 -=,' \Ao, cHs I cg, cHy,c.cH3 <- + e - r_OH + o Y J L C=CH- {-l cH-c- cH3 \y' d", ,6P. ,'6H + HzO {:fl' '!oH <*rl;lH-c-cH3 ULa"r cHr - \ e - +-'9H 6t Mechanismfor conversion of Compound Y to Compound Z: '-8.].n=.""' SEG;'::: - e c?,n 0?s; A. u!ott ? GII* 'cH3 :d 04H - 'L e- \- r OH + H2O e - r O H + t2 '9' NaoH cH3-c. cH3 Itn '9' .c1t - C - C H = C (Y" "'^-"'cHr 5 \A6u Hzo Comf,ound Y CH: cHr Compound Z B. Complete the reaction scheme as indicated. Abbreviations for reagents are not acceptable. Any important reaction conditions (catalysts, heat, equivalents, etc.)should be included.
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