Ochem B Exam2 - Organic Chemistry 322 bL...

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Unformatted text preview: Organic Chemistry 322 bL II:Engagectober11’,2004 g 1/ C “V M Name initiai of Last Name > ‘ T.A.'s Name 1 (40 pts) 2I_____________ (12 p18) . (10 pts) 4___'________________ (10 pts) 5 _____________________ (8 pts) 0 *1 (1 0 pts) 7 (1 0 pts) Total 1. I 3 a “ram UAWM Write the products of the following reactions. Assume normal work-up. Show stereochemistry if relevant. (40 pts.) a /C-OH . \ O CH —————-> Q C \on , A ‘ K: C. #CMt—Ctg CH2'CH3 t : W» =: NH—C-OC 2 Nj/‘kugCO + C H-—© Hz/Pd (M ‘\N/) 2, ‘ H I “N \ . / N b tit: L c. CHsowQE-NHZ fQEL.) CW00©~CEM d. gm “V” 5.3 PM _ 2-0-0H‘E 2 - 2 c:\N 9’ I‘, 0 9- ©~Eeu+ CHa-ES-CHg g.» g’O’CKCCVQz. 1 C) I \, C3 f. Q—ECI + CHa-CHz-E\OH i+©gfo $114501») fi’ ‘fi’ 0 n. c—C ' _ H3 +. CF3-C-OOH ---> QM» c O “S ‘ 2. When you write the products of the following reactions. (12 pts.) 3 “(A . means the isotope‘iO j W J1 l / fl ’4 / J ’C i? it a) Quiz—H CHM 25g. Q’cififc W + Cigcflui R [CH3 (3 l b) QCH2-C-O-%IEHH c\o+ “0" C_\IH\ H a/ch CH3 0 G c) CH3-OT:5> (“I + CH3 . ,_ " Cor MAW, _j’w- (J M °‘ ) If H20 1 a; (rd/30H a / d) Q—C—OCHS W Q’OC + wa AAZ $1.4 #Wfa/fi) Write the structure of the recOvered e er (d) after the r action has proceeded to 50% hydrolysis. - ' I _ . Q {4 5/4 Mr [arc/Kc *2 ('3 1:5 55M...» ii 3. Outline an efficient synthesis of from 4-methyi cyclohexanone and any reagents you need. (10 pts.) 0 o ‘ B Lbfi @DCJJ (/4 F———9 “Li (Dy-see, ‘ A a ( “v0” o C) @950 \ I . “9 Br E i O ‘ BY? H 4. Outline an efficient synthesis of CHZ'NHZ from cyclohexanone and any reagents you need. ( 10 pts.) . H0 CM 6 mm ~ ' ‘HO mo; w 5. Give an example of a reaction which uses each reagent. (8 pts.) (’6 -—Q( 4/ CH3 9 e / [(CH3)3C'O]3AIH LI HAI<<CH2-CH\ > DIBAL CH3 2 6. Write the structure of a specific compound for each of the following. (10 pts.) a. an imine Pk 7/ “yam” b. a y—lactone @ 0 c. I a B-lactam @ “"6 d. a hemi acetal __ Cf“ 7. The Wittig reaction involves at least two intermediates, X and Y. Draw the structures of these species and name them. (10 pts.) 9 i" , P 4—»! \ Q—CHQPPha THF \ / CW 1P \qa I CM \i\:4 /i PPLB 9 a O O \P \Cff “‘5 ...
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