Spring 2006 Exam 2

Spring 2006 Exam 2 - D Please check here if you wish To...

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Unformatted text preview: D 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 (487 KolThoff) during office hours (2:30 - 3:30 M'W'Th' F). LasT FirsT Name Z 3 6% Name QuesTion 1. 8 (PL ASE PRINT CLEARLY) ID. number Organic ChemisTry 2301 Exam #2, March 8, 2006 4. 20 Professor Gary R. Gray 5 5’30 Please answer all quesflons in The space provided. You may not use a calculafor, molecular models or nofes. 6. l/3 The exam musf be Taken in ink in order To be submiffed 7. /§ for re - grading ToTal [I fix”? 1. (8 poinTs, 2 each) Circle The compound in each pair ThaT will undergo The 5N2 reacTion more rapidly. a. CH3CHCH2—9 or (CH3)3C_I I r“ w CH b_ CH3CH2CHCH3 0r‘ l {w a Br £94539}? ‘ c. CH3€H2CH2CH2€| or CH3CH2CH2CH2I 444% CH '° 3 [ff/W d- Br or if 0/ / MM'Vi/K {jewel a“! 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. a v [a > {7 A b CHZOH a. Ol) H+OH a.» E N0 fireafiéfifi L'é‘PVlnfiwilfléffk 2 2H3 é”) 6"? 3"" $1 W ml; $5.52 {‘3 gm C dry 6 l?! ES» 25 £3 {UH or as; @9155? “460 r V e of com. 151%: awhile M lo a; & Br' b I!) a? E ,. C *“s :5 3. (16 points, 4 each) For' each of The following pairs of compounds, indicate whether They are enanfiomer's, diasfer‘eomers, or- The same compound. CH3 CH3 H OH Br H Br H and H OH I CH3 f \ CH3 f5‘30is] emarmfi‘uomwg CH3 b. H3Cm/ CH3 and H36 [:58 42 f5“ 3 5? j fiiaofifiiérefl mfi H\ \\\CH3 H3C” [H c. lc=c=c\ and v’c=c=c\ Cl CH3 H36 Cl ifimflfl $6“ x" H3C H36 H CH3 d. and CH H H3C 3 H36 5:5 3:35;“; my {3, 4. (20 poinTs, 4 each) Give The sTrucTure of The major organic producT in each of The following subsfifufion reacTions and predicT wheTher The mechanism will be predominanle first order or second order. Br - 9N KCN 3 s eco Cl. /K/\ W Mf‘fl\’ylla \% flag as “A” I G) _ “2. ' “ {:9 53b] (*2...) fir oncowrecrtw I Tater ea c;th W‘w‘lrfi lmfi cH3 (3+3 b. CH3CCH2CH3 CHBCOZH (xi—+3,” aw Gfimw “a a | heaT l Pl Veil cl 0 , O \C “O Q r" (it? if” m 3 f \ m u ‘ ® a1 m] C/H‘g NaOH c_ IIIII l l l H CH Br><:> CH3 W D \ l l<::> 3 fl S ecam 6% " «‘3 lm 5‘ r U9 l» 1 ({2} {Cur anwmf 0 gr 3 firstch Wmial‘if'fi Br /H/ CH3CHZOH \C d- heaT ' V‘at a E 1‘: , 59 ® :3 'r 3/” lilo-Sic] if n oi: 6:: r“ m Wow; 3 MW ii» fiecam 0 Y‘all? w“ a) excess NH3 3 ___. ii a. r heaT L ./ C33 5. (20 poinTs, 4 each) Give The sTr'ucTur‘e of The major organic producT in each of The following reacTions. (Bk (1 CH3€HCH2CH3 Bra OH 34%”. CHEM?) CH3 M CH2; (‘9 C.th 0b] CH3 NaOET /\“‘"‘ 044:3 b. Br ETOH \ , @3 heaT [Mow CH3 “L C heaT ' MW [‘9’ Br' I,» CV/«zaéfl CE “toga (NBS = N—bromosuccinimide) CH H m a | 3 l CPI—30+; 3 2““3 ' H3C—C—C—CH3 heaT "=3- fa (Q) I I 6:; \w CH B , _ 3 r 3 :5 (EliminaTion producT) 6. (10 poin’rs) Propose a mechanism To accoum‘ for The indica‘red produc’rs in The following reaction. You musf show each bond-breaking and bond- forming sfep separate/y. H Br‘ I I HZC=CH—$—CH3 %» Hzc=CH—f—CH3 + BrCHZCH=$—CH3 V CH3 CH3 CH3 r“ ‘ If U9 (933 3% 3e Wad“ Br“ (‘9 X “j U 7. (10 points) OuTIine a syn’rhesis for‘ The following compound using The indica’red s’rar‘fing mcn‘er'ials and any o’rher necessary reagen‘rs. O/\/\ from O and MBr‘ £qu TBV [Wm] /‘\ “‘“‘ fig} Br“ Cr / (16%?) cnodik “Ebb Early chemist describe Ihe vim din mohcula -7- ...
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This note was uploaded on 10/30/2011 for the course CHEM 2301 taught by Professor Gao during the Spring '07 term at Minnesota.

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Spring 2006 Exam 2 - D Please check here if you wish To...

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