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

Info icon This preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

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 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern