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Spring 2007 Exam 2

Spring 2007 Exam 2 - CI Please check here if you wish To...

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Unformatted text preview: CI 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 of Professor Gray's office (229 SmiTh Hall) during office Hours (2:30 - 3:30M'W'Th‘ F). LasT F i rsT Name A C% Name QuesTion 1. 69 ( LEASE PRINT CLEARLY) 2. /é ID. number Organic ChemisTry 2301 Exam #2, March 7, 2007 4. 30 Professor Gary R. Gray Please answer all quesfions in The space provided. You may not use a calculator, molecular models or nofes. 6. / 0 The exam must be Taken in ink in order 1'0 be submiffed 7. 1 fl for re -grading ToTaI 4 pp 1. (8 poinTs, 2 each) Circle The compound in each pair ThaT will undergo The 5N1 reacTion more rapidly. Cl. (CH3CH2)2CH—Cl OI" <(CH3)3C—Cl ) [bu-l 37;] [9—4993 C. CHaCHchzBr or [We] fi' rs or CH3—CII—CH-CH3 Br 2. (16 points, 4 each chiral center) Identify each chiral center in each of the following structures and determine whether it has the (R) or (5) configuration. You must show your work, i.e. correctly assign the priorities of the groups at each chiral center. b fHO C‘Ha a. H—(lS—OH 0'14 “also, ol—la’ R H_$_OH L4 é:- o 4 ’ [5/44] CHZOH i \ 0410“ (Fischer projection) C H o H~-— LB 0H \ A [41‘ C(- DH“ 3; “you" Ca V ‘ HA' b 0 / fix a; D E [3'3 Zémj b 0 R c a. — Hal 3. (16 points, 4 each) For each of The following pairs of compounds, indiccn‘e whether They are enan’riomers, diastereomers, or' The same compound. \__/ $H3 $f' CIIIIIIIIC and H CIIIIIIC o 3 ' \ Bra H H4 \Cl 5’ 30 . L— on mafia? Dvwzvg CI b. and Cl [f—zoej . ‘ W 2»me \_/ fOZH fOZH c. H—f—OH and HO—f—H H—f —OH H—f —OH [3,225] COZH COZH Ms‘ker‘wme r3 Bl" $H3 H CH3 d H — f — Br d. H3C H on H _(l: _ Br‘ Br‘ CH3 $ Arm 4. (20 points, 4 each) Give The sTr'ucTur'e of The major organic producT in each of The following substitution reacTions and predicT wheTher' The mechanism will be predominanle first order or second order. C [IV '17 a] b. [L'lfl 5] CH3 I CH3CHCHzBr I CH3 Br 0% 3 heaT LCVS": order ___> CH3OH A?” Scams? Order WLWB CH3CHZOH he“ Cr em r.) Tirst order OWLOH‘S CH3CHZOH j/ heaT Ctr Q1“ mi“ order 9‘3 Efl’ H ' C." DH H20 H ’3.» 0H 3 £441,043 55“,“ at 0 rder (Fischer ProjecTion) 5. (20 points, 4 each) Give the structure of the major organic product in each of the following reactions. K/ CH3 OH '5 I NGOCH3 \ a. CH3CH2CCH2CH3 W 0H3 OH :: C.- Wt 644 3 I 3 Br C 0L3 1" ‘L’Vms [sz7h] ’ b, CH3CHZCHZBr w CH3 0H7, cm, a, egg-44 [ér ’4 (931 H C & é CH 33—» CH ‘ ' 3% C' 3 | | 3 hv 3.41,.“ Cr 3 CL! ”#2 c] H H H B r‘ K/ (monosubstitution product) CH3 ——-—> d' Br CH3CHZOH [ G '40 L heat H35 H OH W e . I CH3OH \3‘ _,__ / 3 - H3C—C—C—CH3 ——> C- “t | | heat ‘ / \ C. V’ ammo) \/ (elimination product) 6. (10 points) Propose a deTai led mechanism To account for The indicated products in the following reac’rion. You musf show each bond-breaking and bond- forming step separafely. Ml-Zeb] OCH CH CH3CHZOH 2 3 OCH CH hear 2 3 CH 69/ “”6333 ”H H“ / G) LKQ'D/E‘t‘ 44991 CH3 (443 we , MEL ’EJcDW7 Q/Ktt / 5‘43 7. (10 points) Outline a synthesis for the following compound using alkyl halides of four or fewer carbons as starting materials. You may use any other necessary reagents. CH3CHCHZCHCH3 | l CH3 CH3 ”33%“sz 0‘45 < ‘ l. LL Wag/H‘EQM Lb W 0H3 ELM-4% (at w I) a re (0143? ”Lilla; + Mai/HWBW 0‘43 01:43 I. L.’ 2. Car WE?“ WILEY" (Cl O‘rI) “i3 ...
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