Fall 2002 KEY - I Final l. ( 42points) t -t n r. ' f...

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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 possible outcome, 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 oYvo \J (NBS) CH2Br 'a CCla, hv (rn-= Q- = cuur) (c) o ll 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 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,. .( H o-.,ro cHacH3 17 CnHzA Cl N OZ (ionic compound) 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 zoH o CH3CNH 9 lrl 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 boxes below, provide a detailed, step-wise mechanism using the curved arrow notation for the following base-catalyzed transformation. tor ll *Gcll., | il "+ \,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 Ol tO''- ri ^.. I ^. . \"_q" 4 y.c-cH2-c-cH3 -=,' \Ao, cHs I cg, cHy,c.cH3 <- + e- r_OH + o YJL C=CH- {-l cH-c- cH3 \y' d", ,6P. ,'6H + HzO {:fl' '!oH <*rl;lH-c-cH3 ULa"r cHr - \e- +-'9H 6t for conversion of Compound Y to Compound Z: '-8.].n=.""' SEG;'::: -e c?,n 0?s; A. u!ott ? GII* 'cH3 :d 04H 'L \- r OH + H2O rOH + t2 '9' NaoH cH3-c. cH3 Itn .c1t -C-CH=C (Y" "'^-"'cHr 5 \A6u Hzo Comf,ound Y CH: 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. zot.oH \/ '-> -T*CHr C6Hpo2 "4ff;, cHr f3 draw major stereoisomer o ll rr t"o"'o1.= J' Fn, ,'"-'t.nr-i-c-
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This note was uploaded on 03/19/2011 for the course CHEM 216 taught by Professor Nolta during the Spring '07 term at University of Michigan.

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Fall 2002 KEY - I Final l. ( 42points) t -t n r. ' f...

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