Exam_3Key

Exam_3Key - l) (10 points) Predict the product(s) of the...

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Unformatted text preview: l) (10 points) Predict the product(s) of the following series of reactions. If more than one product is formed determine which is the major product. 0:1 CH3I (excess) ———* or; I. m c» \cu c Ir CH; HDFMAQQ . ‘ +\ heat E\\nu\a 0“ f 2) (10 points) Explain why the following bromoketone for-Ins different icyclic compounds 1‘ % Pndgr different conditionsgflce A 4:. MN) 3mm (qua M Sw‘ “km h f C l v“ A OW 3" w \ (97’ o ‘ \ kmdanaw cg MeO'/25°C 5‘ Wk Methanol O .. \‘v N \ 0 Wu wand» Br —78°C \ LDA (t, no; act: 51).“ cu; Val/m 3)(lS points) A [3,y — unsaturated carbonyl compound rearranges to a more stable conjugated 0t,t3-unsaturated compound in the presence of acid or base. A) Propose a mechanism for the acid catalyzed rearrangement. B) Propose a mechanism for the bas zed o n O rearrangement. o H u 9 ‘4 DH, I t % o o , ,——>7 , 4 E b H‘r or OH‘ E‘ an CL, {3 unsaturated carbonyl compound m! L- 30“ D\ go ‘3 (\o‘. C?\ en 7 p .. {of ' J \ “root: t, \\_T A . l \\l"*‘ ' ’ Cy" ’ in! m H 4) (15 points) Rank the following compounds in order of increasing acidity With 5 being the MOST acidic and 1 being the LEAST acidic: no 0 /\OH finch. a [5,7 unsaturated carbonyl compound C) O 5) (15 points) The Wieland—Mz‘escher ketone is a valuable starting material used in the synthesis of steroid hormones. Give a mechanism for the following transformation: 0 O Wieland—Meischer ketone/+ \A a- 13! L 4 (1/37): 6) (50 points) Predict the product(s), assume an equivalent unless otherwise indicated. a) O 1) LAH + ’ CI 2) H3O b) 0 \JK 1) xs CH3MgBr _-—> OCH3 2) H30 0) O (Ph)2CuLi —> NH2 d) o 1) LDA ———-—> OCH3 2) CH3I e) O 1) LDA —> CH3 2) CH3I O PBI‘3‘B r2 f.) /\/‘L OH O O Br/W Br 9 ——__» NaOEt/EtOH EtO OEt excess I) NaOEt/EtOH _——> o 0 H30 OEt 3) OH" 2) CH3 CH2-B r 4)H3O+/ heat 7) (15 points) Propose a synthesis for the following compounds from the starting materia1(s) given. 0 0 \ H a) Q 5 ‘PWBLEBA H“); t\)\\,\, “0}? a 0‘)" 3k L i? \ 9 on m 9v 9‘ C“; “" G H a” \ 6—» L/ H —/ 0H 5 no“, b) O %* 8) ( 10 points) The following reaction is known as the benzoz'n condensation, The reaction will not take place if sodium hydroxide is used instead of sodium cyanide. Propose a mechanism for this reaction, 9) (15 points) Using the attached tables, please determine a reasonable structure for the compound based on the spectra below. thlllllll“ lR Spectrum (Liquid mm) 1750 4000 3000 2000 1600 1200 800 v (cm‘1 ) 100 Mass Spectrum 80 50 107 "/n ol base peak 40 +- = 20 M 150 240 280 120 160 200 m/e ' 130 NMR Spectrum (100.0 MHZ, CDCl3 solution) expansion DEPT Csz’ CH3+ cr-rl expansion proton decoupled __.|__L.__._L.__J.___l__1 __l_l |.____J__l__L_l 10 9 8 7 5 5 4 200 160 . 120 80 40 o 5 (ppm) 1H NMR Spectrum 3‘)! (400 MHZ, CDCl3 solution) EXPBDSIOI‘I . 19‘ g,“ 73> 7.2 70 ppm TMS “j? O (1143 UV Spectrum Kmax 265 nm (logwe 2.6) lmax 271 nm (109108 2.6) solvent : melhanol \CHg ...
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Exam_3Key - l) (10 points) Predict the product(s) of the...

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