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2008f - I Please check here if you wish to have your exam...

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Unformatted text preview: I: Please check here if you wish to have your exam returned to the boxes outside the classroom. Exams not returned to the boxes may be picked up at Professor Gray's office (668C Kolthoff) during office hours (2:30 - 3:30 M-Tu-W-F). Last First Name é §§_¥ Name QueS'l'ion 1. l 0 (please print) ID. number Organic Chemistry 2301 Exam #4, December 3, 2008 4. Z 0 Professor Gary R. Gray Please answer all questions in the space provided. You may go_t use molecular models, a calculator, or any notes. The exam must be taken in ink in order to be submitted for regrading. 1. (10 points) Propose a detailed mechanism to account for the product in the following reaction. You must show each bond- forming and bond-breaking step separately. H ea 0 heat HO \_ H \ 624 .44 Q7.” ' 0/70 4:2 95/90 —-—-> (Bowl, @3 e) @ if 2. (40 points, 5 each) Give The structure of The major organic product in each of The following reactions, being careful ’ro properly indicate sTereochemisTry. If The product is racemic (i), so indicaTe. on _ = _ 1. NaNHZ . fl (1. H c_c H —2.Ph-(II=O> 0H3~T’C:C’H (01;) 3. H20 H H b. \c=c’ 1'—Br2—°> l—l—— EEC-"(GHLBb’C/Hg , \ 2. NaNHz, 150 c [0,4253 H (CH2)5CH3 3. H20 (S) H /i3r c. H—CEC—(CH2)3CH3 129nm> \ -—-c . \ [674%] u (D ((442); M43 3 9 CEC‘H 1. SiazBH > ’ d- 2. H202,NGOH @ Sia 1' (CH3)2CH$H— 69 LOT 8 0‘ CH3 Ques’rion 2, confinued H \OH 500 e' >\/\/ -——->0 2 (59 E ] (re/térxfican) H’Waé, E I 0 E9 L‘C S‘Fereoafiwm Cnoorreot’ or not Dem/f CH3 “+3 f- PBr' . _>3 U (”Vermon} OH ”Br (Seen—me} (—3) VP stareomrm («‘54 can 2. 9f“ 0r n at" (Law — G) e D Cr03- N—H-CI 9- NOH C NKH (9 (no 6»;th ('W' ambuxylfc Ma) CH3 ' 3 h_ HCI at 5’ OH ZnCI2 3. (30 poinTs, 6 each) Show how you would accomplish The following TransformaTions in good yield. Please wriTe The appropriaTe reagenTs over The arrows and, if more Than one sTep is required, iTemize (number) The sTeps in The order ThaT They would be performed. You may use any oTher necessary reagenTs. @ 0 a NOH l.T5Ll, F3”’E“‘~/\/CN ' z. KCN (3‘) [H404] é) o /. /+CEC9Nfl/9 ll b. CH CH CH B —> CH CH CH CCH 322r2./42,00) 3223 H 50.; a3 4’3'lla L ( 1 [435045) 0": A”? Et °Z.0HCHO; .# 6w I 6750, ‘JQ 3 163 4 /'A/flr’l/#[email protected] H\ ’CH3 OCH-H 2. 0/432?" é) C=C\H C' 3. Ma... 0 N‘é (£7) Q CH OH /‘ FCC @@ OH 0/ 2 z, Eff/775K OA/ (+) d' We; ' 3.14 o [IFVZJJ 5 /. 73c,” Aw” Aw)@ O 2, m5, €262.04) 0/0“on 6. 3. HLCSQ @ (see/mafia 4' #306 a) i. iO-IBL] 4 4. (20 points, 10 each) Outline a synthesis for the following compounds using the indicated starting materials and any other necessary reagents. xv, OH a. M from /\ and CH3CHZOH (LY 031- Zptjv' . CC I. CH3£HO® M33459 @ gsr‘immwni' 3k (+3059 59 w “45.43.44 Note: 73% 1W- M30 TV” mamwmim 0‘9 dawn. loorwll macro MW) OCH3 - OH b. (1) from and alcohols of four [1 MW] 67 or fewer carbons 4 l. KorV‘l—li ’ x 2. W33r® wars 6) ‘ 0‘4 \PB‘"; ® 3 . 0/815} a; 64430” <78 ll 63 ® l H30 8 m5, ra’cw oT P39, ““1 " ll a; a a) (Algal—l / /\/ <3, WM] 3 r“ @i HICVW * ...
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