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Fall 2008 Exam 2 - I Please check here if you wish To have...

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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 (6686 KolThoff) during office hours (2:30 - 3:30 M-Tu-W-F). LosT FirsT Name A g Q} Name QuesTion 1. Z 0 (please p inT clearly) 2. Z (9 3. ;:CD Organic ChemisTry 2301 Exam #2, OcTober 22, 2008 4, Z 3 Professor Gary R. Gray ID. number 5 Z59 Please answer all questions in The space provided. You may use a 6. Z fl calculator bur nor molecular models, notes or orher elecfronic devices. 7. /p ToTal Z 0 0 1. (10 poinTs, 2 each) Arrange The following compounds in Their order of reacTiviTy in 5N2 reacTions (fasTesT = #1, slowesT = #5). CH3C|HCH2CHZBr CH3CHZCHZCHZBr CH3CH2cHCHZBr CH3 CH3 #_3; # Z #_‘Z_ 9'3 CH3CHZCICHZBr CH3CHZBr CH3 # f; # / When 2-buTanone (1) was reduced wiTh a chiral reducing agenT, The producT (2—buTanoI, 2) was found To have a specific roTaTion ([CX]D25) of +11.07°. ("7 9H CH3CH2€CH3 —> CH3CH2CHCH3 1 2 a. (3 poinTs) CalculaTe The opTicai puriTy of The producT. Pure (+)-2-buTano| has [0c]DZ5 = +13.50°. You musT show your work! H.07 043-: -—-————-'X100 : 320 1350 A b. (4 poinTs) CalcuIaTe The percenTages of (+)-2—buTano| and (—)—2-buTano| in The producT mixTure. You musT show your work! .- 0/0 6")‘Z’BMDH : f2” 7“ ([11:62, 9/ 9/0 2L ' % {-0443pr = ”M” .1» 9% (a) 2.. c. (3 poinTs) (+)-2-BuTano| has been found To have The (5) configuraTion. Draw a Fischer projecTion of (S)-2-buTanol. 043 I H—fi-noH an I . (443 (20 points, 4 each) For each of The following pairs of compounds, indicate whe’rher' They are enan'riomers, dios’rereomers, or' the some compound. 0. H" [OH szOH /”C\ /CH3 d HO—f—H on Wu; HOCHZ“¢C\O H—f—OH H H CH3 CH3 CH3 | H OH H—f—OH and WW H —c OH H OH CH3 CH3 CH0 CH3 | | H—f—Br‘ and Br'2C\ W CHO CH3 H H,’ CH3 CH3 , /Br "’c=c=c and ”C=C=C We!) W ’5 / \ / \H Br' H H 4. (20 points, 4 each chiral center) Identify each chiral center in each of the following structures and determine whether it has the (R) or (S) V configuration. You must show your work, i .e. correctly assign the priorities of the groups at each chiral center. b ¢>bvcv& CO ' - , Halt] é2H g N0 Crelil: gar Wrrecf a. — — x .n \ 3 éH 0‘ "' MSNCAI C—F ProDWb “be-3 3 c axe, ass chmi Cncw v «I '7 EH 0, I 3 b HOIIIIC\ E H/ CHZCH3 Cl 15 b, l CH3 l c. b ‘ C ‘ [I] H 0‘ R H36 4. CH2 l c. ,1 l “H C l E l O 1 d / 4’ M (j 0 l R 6“ b l -- (l H l \J g l (20 poinTs, 4 each) Give The sTrucTure of The major organic producT in each of The following substitution reacTions and indicaTe wheTher The mechanism will be predominanle first order or second order. Hint: The sTereochemisTry and bonding order of aToms in all producTs musT be clear. CH O I 3 (1H3 a. CH3CHCHCH3 + Cchl— OH —> 0H3 LHleFCelz (“3““) CI Pr‘a‘l' OM/WB anger @ 0/! 0 H ll 6-) én‘D £t\HNl‘l'3 Val ( £0\ b + NH3 C Sewvwll $ 0% (D:2H) Molar @ (um: \ ® CH3 0”} C- I + CH3CHZOH _. 0044—ng first Oral” ® ® CH Q”? d HC c3CH I OH c our . —- — + H0 ———> -——-— my 3 I 2 2 AgNO3 2’ l 7' CH3 first 0 H L rear r.) arolu' C3) (9 943 0H3 — — + N OH ——> e- H C Br 0 H20 Host-H sz Secomll A”; (cm/WW“) CH3 I 0PM!” “+3 C3) 6. (10 points) Outline a synthesis for the following compound using alkyl halides of four or fewer carbons as starting materials and any other necessary reagents. r3 CH3CHZCHZCHZCHCH2CH3 \ 3 . C79 Wawwiwufiar «- (W'gw-zwfi-{GwLu €43 , T i. Z Li. C79 CH3 1..G««IT® i C443 0H7, C44"? r ® Cine/Q strep com/M M50 (0%: (W30HLLHLWL5'Z 0,44 L: + (Av-i3 ngjiw (10 points) When 1-bromo-1-methylcyclohexane is heated in ethanol for an extended period of time, three products result: one ether and two alkenes. Predict the products of this reaction and propose a mechanism for their formation. Your mechanism must show each band forming and bond- breaking step separately. Predict which of the two alkenes is the major elimination product CH3CHZOH (fiat forth 2. + 04:: heat Q) IMA/iowrCD fl 71L“ E L’Dl-l L‘Bre -- HQ/ll/QD lo lilK-‘J for» m s Q 7’ d” 3 Eb“ Old? “9" ‘7 l-l H GD @ EtoH [(94 Ll] a. ...
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