31mt3F07 - Problem 1(40 points Give the final products for...

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Unformatted text preview: Problem 1. (40 points) Give the final products for the following reactions. If no reaction occurs, state so. Be sure to Show the correct stereochemistry. Circle Your Answer (A-l fi 1) CH MgBrfiexcessVl'HF ' H l A) __ 3 Q-C'H + C d]. c OBI-l3 2mg D“ I .7 3 at} (j‘ll (+1) 31’ 1) ijwrm: - B) D—c—OCHS 2)H30+ D, Qua-or“ + CH 30’” (3*! l (+ H CH3 1 O CH NH w u ‘ 0“ (+57] C) 0 ___3___=_.. CH *cH-CML-qIL~C-WH 3 f H20 ‘3 0 f? 92‘ D) WOO—é foam gflwfimmflm 5-930 \ : C‘ 'C’HB + N L! 3 t CHM G l O 0 L10 L—j “ 1| -— ' “4 E) mfgtmzo v. If- NHJ C1 + CH3 ' l)lDA,THF / — _O ._ : 0 + 3 1 F) 0:} 2}CH2=CH-CHzl3r L/ ( H) CHEBr 1) KCN I acetone {,1 .T' C- H; ' Lay + N I 2) 1430+, heat [:2 ,l Problem 2 (20 points) For the following reactions determine if the equilibrium lies to the left or to the right as drawn. and circle the appropriate answer. Circle Answer fi TI) 0 0 H H M HGC/CRO/CHCHa +CH30H Hac-c‘o‘mocHa+ HO’CMCHs IEFT RIGHT 0 NM- 0 a) 3; a II H30”- “‘03 + NaOH HzC/C‘HQE‘ +H20 LEFT RIGHT O ._ if 0 if (E C) c ” /° /°-- + EtOH “\ H30” “‘“OEt + Hie/CECE, = H30 \fie OE! LEFT RIGHT O N O O D) H 13+ El, 5+ (I; H Hac’C‘NHa + Hzc—rcaoa H20” “*NHz + Has/0‘05: LEFT RIGHT O Na+ 0 I! e I! E) NaNHZ + Ric/CHOIR ========fi HzO—IC-aoEt + NH3 m O ('1 F} H30!” "'--OH + SOClz 1° Haciacf + 802 +HC1 LEFT O Na+ 0 Na+ ‘0 0 II a H 9 || {1 G) HSC/oHNH2 + HZC/Cmcfia m Heca-‘CHNHE + Has/Cwé o o o o H, II 13+ n 1: g 8 H30 fiicmo“ “HT”— HaC/Chfi/ Moi N“ LEFT RIGH? 2 o o ‘I? “i E 1,1 I) H c~"“3“*-I\:HCH3 + HacflcucOH .Hao/ ‘0’ “CH5 +CH3N$12 LEFT mm o o 0 0 u u g g D Hac/CHCI + H3C’E‘CAHOH m HSC/ EO/ HCHG + Problem 3 ( 10 points) For the following molecule, what final products are formed as a result of decarboxylation upon heating? Given the mechanism for the reactions. 0 0 H II Ho’c C“‘"OH O O “J 1— o F' HO‘C'h C“) \C’éq‘l H29 \¢:o 7 .zumu + ’l 0 o (+3) Problem 4 (10 points) Employing Dieckmann cyclization, what starting material would you use to synthesize the following compound? Show the reaction path. 0 (IEHOCH2CH3 C) . (Ta c..-0 _... {J (.4343 Er :4 Hf 0 E' I: “'4 .0 ’ ,ool "—3 " rare; 3 a L H 6‘5ij 0 o 0 m4 J o 0 ft Infra“? _ n H “00! Ct?) EL ("0” H - f 3-0?) C l” .6? " 7 El c~0ouL Problem 5. (10 points) Starting with ethyl acctoacctate and any other organic compounds, how would you synthesize the following compound using the acetoacetlc ester synthesis? Show the. reaction pathway. O £\CH3 o O 0 0 c113, 2-5-44 -2-0€J 90%"; CH3~ 11—55-506! ._ e.“ m 5'" E; 3,. L2.» 33: 0 no 043- 20— aggoou HWWJC Hs'IC—‘jH'C‘ ‘0“ H m 1) C02. '1’ I I; ,W P """'——'D ...
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