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Chem 2301 - l:l Please check here if you wish to have your...

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Unformatted text preview: l:l 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 during office hours (2:30 - 3:30 MWThF). Last First Name [12% Name Question 1. 2- '25 ID. number Organic Chemistry 2301 . Exam #4, December 2, 2005 4. &0 Professor Gary R. Gray . Total / 0 0 PleaSe answer all questions in the space provided. You may £91 use molecular models, a calculator, or any notes. The exam must be taken in ink in order to be submitted for re—grading. 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. Ohmic] OH <>< OH H2504 CE; / (Ph: phenyl) C\ 69 Ph/ Ph ph \6') ‘44 ”lief? dink?) 2. (40 points, 5 each) Give the structure of the major organic product in each of the following reactions, being careful to properly indicate stereochemistry. If the product is racemic (i), so indicate. CH co 2. - a. \c=c’ ——->l: 03H l—l ”C9 'CDV‘ ’ \ 2 on correct H 502” H 00H Slz’eireo («la M team (9 C01” (Fischer Projection) c H2 CHZIZ b. Zn(Cu)l (9 l: 8‘44 3,] , (Er C 0—CH3 35:4, 14 . (if) Z®néorr¢ Pt 2 2 H0 Dl-l a) are??? S'l'PJ/eodfim [9—447 h] ® not as...» Q CDT anfl'td H35\ ,H ‘ Clz 4 OH: H StereoolM/wu d IC=C\ H20 [Hi (5h) 0v- 6.. '9 H CH3 4" (D S'l‘ezreovlvuw CH?) Mt char [944 A] @ (Fischer Projection) Ques’rion 2, continued o H o, H so a. CH3(_CH2)3CEC—H 1.9534 4 “+3 (Cfiz—irg—‘C’HS @ (4-1\a,:( ® #r‘ emol _ Na CH}, 14 f, CHa-Cr-C—CHzCHa ‘_’NH3 ¥=C/\ / E5343 '3] H “2.4643 NGZCrzO7 g. CH3(CH2)5CH20H W 5H3 (CH1) b 60;... H (“’94 no ovum: 4‘0"“ MYA‘ h H3C OH SOClz ng‘ ' Q C”: [Ii-1J6] (dicing) E? gr ‘Erms Csomer 0 f L-c $£¢V€OM not dwr (30 poinTs, 6 each) Show how you would accomplish The following TransformaTions in good yield. Please wriTe The appropriate reagenTs over The arrows and, if more Than one sTep is required, iTemize (number) The sTeps in The order ThaT They would be performed. You may use any oTher necessary reagenTs. @ ® ii 1.12%. Wle myrx 9H 2. Au‘oh‘fi/ @ éHs ® 63 OH Br I: Mg) Etta b. O 1- Grier/HO 6‘7 CH3 l 3‘ 40609!ch @ e) o c. /\/OH . TS Cl J Parwlme /\/NH2 2. e«Woes: ““4363 l. PB“: ® an excess Hid-3 (ED 0P l. PM Dr Crag-Zpyr- 0'" CHZOH 0? Inner; Reagent @ d. 0/ 2. Etng @ 3. A—afify C23 LBW), @ H c H H c CH CH CH e 3\c—c/ 1' KOH’ 13$ 3\c—c/ 2 2 3 ' _ _ \ HI \CHZCHZCHg 3‘ H19. Pol/Besw H/ H Quévxou‘ne CLdmfi law‘s cat'oijsfl (D (20 points, 10 each) Outline a synthesis for the following compounds using the indicated starting materials and any other necessary reagents. Br I a. H3C — C —- rCHZCHZCHZCHB from H—CEC—H and compounds having four or fewer carbons 24266 HBr® H’C?"'"H @ C HEN} 7314 Li a v- or exc ess Na, MH 2. ”*0 :C. (064133 (443 é-——_—-——— H’CE‘C —LL WSCWLE'EY‘ (No.5 (‘9 OH I b, H 36 — C EC -- CH— CHZCHZCH3 from H-CEC—H and 1-butanol L [email protected] 0 1, wbwz%a”l4 4 Cr03' 'ZPYV‘ @ @ Cw: -Hc| (Pee CHyCEch :Prr ) ”X 1. MLNHL orBuLL @ fl;§:;§$€:\/ 2. W31- (Or M3010? CHER“) Met—owe. H'CE-Cf—H @ CjoYULS MW) ...
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