spring2006 3key

spring2006 3key - D Please check here if you wish To have...

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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 KoIThoff) during office hours (2:30 - 3:30 M' W'Th ‘ F). LasT FirsT Name [l €¥ Name QuesTion 1. /3 (PLEASE PRINT CLEARLY) ID. number Organic ChemisTry 2301 Exam #3, April 5, 2006 4. 36 Professor Gary R. Gray Please answer all quesf/‘ons in The space provided. You may _ nor use a calculal’or', molecular models or nofes. 6. / The exam musf be taken in ink in order To be submiffed for re -grading ToTal /pfl 1. (10 poinTs) PropOSe a mechanism To accounT for The indicaTed producTs in The following reacTion. You must show each bond-breaking and bond- forming sfep separately. CH2=CH—CH:CH2 CH2=CH—$HCH3 + BrCHZCH=CH—CH3 equnv. W H ‘ Bl" f// 1"” a, '5 ‘ I 11}, ac M} :Q Brit; 3 (3i?) , ,. , as ; CHI ml » all 5% fa {:pr 1 {A «w M»: 5 @ 2. (12 PoinTs, 4 each) Give The sysTemaTic names (IUPAC Rules) of The following alkenes and alkynes. You musT assign The configuration of double bonds using The EZ—sysTem (if necessary). 4 5' _ ‘5 / 0 e2 @2 a a 524,2 [fiéfiij -« 3~figgfify47€ri 3"" €Wfi 52w -v Barman/fly!» [y‘afifwm é”) I 1, g / b. 2! 3/ if, I’ If :7 {1* C “M i? ‘ ‘ I”) w? .w M ' .fl my Ge“ [7&3] 03?, 3E) '9 V” {/é; 5f)vc>/c/z2 Await ’45:“ 5/53“: (:3 W 6x diff/em - (Z3, )» axm If, I 1,”. a (2) {ix (725;) [(7% 553%? 3, 3'" m E: f%y/6a f w/r yflé: yr» 3; .3 w» git/w biz; 7Ltffia 0 (0 £9 3. (20 Points, 4 each) Give The s’rr'uc’rur‘e of The major organic produc’r in each of The following eliminafion reacTions. Ph a ——> Cl. H C H CHSOH \, “fiWn‘LC; ,5 .. 3 / \ 74%] Ph (2443 H (Ph = phenyl) L}; .w “Ev {SMWWW Ph Wu H b_ H Br‘ ET3N \; /’ "PM 7 Br. H hea’r / m \ A 69‘ {war 5:: —~ 15m?»va CH3 CH 4 C H Br‘ __>NC‘I '3" Z- /a "is ' In mg; 3;, Br CH H ace’rone H/ \ H ,, 3 £3; r m (Emir-w 1"“ H2504 @ ” d. hea’r yam KOH C“ CHsoH T”; w /3m¢2§5~W/5reéésf 4. (36 PoinTs, 4 each) Give The sTrucTure of The major organic producT in each of The following addition reacTions, being careful To properly indicaTe sTereochemisTry. If The producT is racemic (i), so indicaTe. M /’L M E ——> N mm,“ a. \ 2. H202,NaOH «if \ '/ «m», ‘ G [gm/5953535} ‘ 695% Cal) Pr W A b. /\(\/\/ 2, Megs fl + 5) KN 2“” _ (9 MM”; 557% TC! c. in M R/«jhuc’ " CHCI3 a) £52273: ] V gr» {:Sayng H3C\ /H 0504 d /C=c —> H ‘ mm: (it) . H H202 ‘ Hz”) w» i a) ‘3‘”39’6 "9’ i _. k. ,2 (:5) fir (Fischer Projecfioh) "(I)" ‘SQHWV Question 4, con’rinued £9 1. h C C C CEC—H I: my CWH 6. H3 H2 H2 2' HZOZINGOH 014/3 ffzmi’ 2’ 5/ , 7' L. 9 3313; Sid : CH3CH_CH_ I | CH3 CH3 [1455' (fr ééfl' é)?“ fair???) (jarrec/f Wm]? H CHCI3 N C E —_> f- 50% NaOH, H20 C Cw g , , Jr 5’ 51x 75an I H CH3 Hg(OAC)2, H20 __“—> ‘ 9- 2. NaBH4 C (M! of _ NC! H3 / h H3C—C=C—CH2CH3 a z: I IIqUId NH3 \ M. u fit I I (A, Qvijéf If (A! z 11;?‘45 _ H20 I H2504 CH3 H9504 [/M tragic? AW éévhfi} A i 6143 33+! 59% 55% 6% 0m érc’a‘fé ‘zL- MMw/M £21” Corréaf Em?! 5. (12 Points, 6 each) Show how you would accomplish The following Transformations in good yield. Please wrife fhe appropriate reagem‘s over fhe arrows and, if more 1'han one sfep is required, ifemize (number) fhe sfeps in 1'he order fhaf fhey would be performed. You may use any other necessary reagenTs. CH3 (3‘) g /‘ Mr 54%,, A a. 2 ' x a? W fl m, g L 3% a" géj flw /-/ 0 4:. / a r» Mn 53> 5/) [Lia/I H3C /CH2CHZCH3 /- Brig” \ b /c=C\ H—CEC—CHZCHZCHZCHs H H r .2. A/xz. Mi!ng é) 3" m “595%! (:4 #1} 6:? gm”) (10 points) Outline a synthesis for the following compound using the indicated starting materials and any other necessary reagents. HC CH 3\ / 3 6—6 from H—CEC—H and CH3Br' , H/\/\H Q ’ Xi («H 73% lvflép 3* a H—w (.5: cw icy?) J4 {fig} on?) 6,643 (9’ //» We”; z» .. ‘f‘; 5»? 1 5H3 73V" *5? Dilbert: By Scott Adams THESE ARE SOME OF THE ADVANCED MATERIALS I'M DESIGNING AT WORK. THAT JAR HOLDS A PYROPHORIC A PERSON FROM A WRTER HAVE SAID “wt-(AT DOES ” $ ‘PYROPHORIC’ ammo mu Unllld rum“ 31min“. music; 3 O Q J O 1 a a, 3 < D E D 0 III E . Ill 2; VS ...
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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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spring2006 3key - D Please check here if you wish To have...

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