Chem3BFall06PracticeExam2 - EXAMINATION 1 Chemistry 313...

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Unformatted text preview: EXAMINATION 1 Chemistry 313 Name: Prefeasor K. Peter C. Vollhardt [Print first name before secondl Use capital letters!] Fehraar}.r 22.. 1994 Please check the natue of your TA and corresponding section number. Complete the remaining information if applicable. 10'] David Rea 313 Krista Beaver 1112 Michael Lai 411 Deepak Sonthalia 111 Sara Cherry 412 Alicia Albert: Wright 112 Barflyl Benin 413 Hmm Iin Kim 113 Anita Huang 414 Sun Firm 211 Jermifer Fujii 511 Holly Weaeling 212 Kevin Cammack 512 Me Movassaghi 9.13 Born Pham 513 Abdolreza Siadati 351 David Rea 601 Lecture Only 3112 Demetra Panomitros T113 Stephen Ivfifls 311 Matthew lefltett 11.14 Arvind Rajpal 312 Josh Levine ' llillllllll HJHI'IIIIH Maldngup anIGrade mmm,plcaseindieatememesterhtwhiehyoumokprevimcmaflmflfi J Please unite the answer you wish to he graded in the spaces provided. Do scratch work on the back of the pages. This beer should have 13 numbered pages. Check to make sure that you have received a complete exam. A good piece of advice: read carefully over the questions [at least twice}; make sure that you understand exactly what is being asked; avoid Skippy stmchlres or phrases, it is better to he pedantic in accuracy! GDCHII Luck! ' (39) (so) (60} {an} (30) TOTAL (2th #7215355“ H|H CMIW 33, Examination 1. Page 2 1. {SD Paints} Nam: (IUPAC) or draw, as appropriate, the following molectflas, including their stmmhemistry. a. H pHU :- Hex—1-ynai3mne Chamid'rry 3B. Exarrdnarian I. Page 3 Br ‘H 4FDxD-2-hexynal 11. [5D Paints] Add 1111': missing compnnants [starting materials, magmts, 01' products] of :11: following reactions in the boxes Ermrided. Aqueous workup [when raquired) is assumati to be: part (if a step. It 151911331": of any answer. 3.. Ckemisflj) 33, Examination I. Page 4 CEHE Ii . CH3 \ / CH3 3. mun—p. - O IFI: v x: 335D. 13725 «cm-1 Chmim'y 33, Examination 3. Page 5 H30 C‘ICHah W ' m 014300011 0 . D - ll CH ECHO NaDH H 0' £1 ( 3)3 + CH3CH $2.3 Chomiso‘jl 33, Examination I. Page IS j. ‘5’ fi' _ H+, Hgo. a GHECDWGDGH3 fiHgCDDH.-CH30H G4H502 Ell [fifl Points] A rosoarohor porformod 13m: Hell-VoIhaIEI-Zofinsld bromination on butanoio acid and worked up the nation mm with sodium othoxido in eflmnol. The product A was a liquid, 11p. 145°C, which dooolofizod bromine solutions- Its IR and mum SPECIIE are shown below. The. UV spoon-om rovoaJs an absorption at 314 nm [E = .5). /\/fiv\ 1. F'.Br2 DH 2. NEWCHQCHa. CH30H20H A a. What is A? b. Intorpmt tho spectral data as roqoostod in the spaces profit-1:11. 1. IR Spoon-Lon m llifiggllliflIngfiEfi-‘oooz -5 .- -~ ...::..-.- . 4. mom no. mt“ 4" ‘ . . - . 113m IE! um“ ‘Hli 'EiF'? ."l ._ I -"""III- illij 15:! .u- I _-_I I _ -._E . . --I.:-'+H='=- '1 - E 1. ..Il _ I | ,E : . r ' E .- =- II-illl I'!T'_" ..= .t'i'_"r""_ '1 T5 - ...I ..I-I..:: | | ' : :_':_ --i—- I' i. I . ._ . ..l__T.|._I. . - EEEH I- |. -: 3 ' | ' nmmmam in n- I '--_—mun—Immarnummnmnnuwmnwmnml mfll'l II: m m II II In mfl'l Comm on the pom at 29% and 1730 our]. Chemjsm' 33. Exanfinarfon I . . Page I? :2. 13c NMR Spectrum 1 1m 14:: 1241 ‘ s an - an a PP“ Number offincs, chemical shift assignmmts. Charmin}! SB, Emuflmzrian I. Page 8 g E IrIflI'I'I'II'I'IIfl-HIIII III "I'll-l1 IIJTI I'IJlfl'l'llfiTl'Ell ITIIJTI 2mm" Integrafion, chfimical shifts, muifipiicifias, assignments of absnrpfions. The wactrum is repaid as follows: E = 1.24 {L J" = 6.3 Hz), 1.33 (dd, J = 6.3, 1.7 Hz), 4.13 ('31. J' = 6.3 Hz}, 5.31 (dq, J = lfifl, 1.7 Hz), 6.95 (fig, J = 115.13, 15.3 Hz}. Chemimjr SB, Examination 1. Page 9 4. UV Spacinm Assign the absorpficrn to a funcfiunal gruup. c. Formulate a detailed mechanism for th: formation of A. Ghanaian}? 33. Examination I. Page m W. [30 Pumts] Writa detailed mmhanisms ta explain the fallowng obsarvafiona. &. / H+ Baha- \ (Shawn? 33. Ermuinmfon 1'. Page H CIH £1. + OH NH3 _... NH + EHECI Chamflfly 3.3, Examinan‘on I. Page 12 1.7. I30 Paints] Profida a reasonable mtlmtic route: fmm starting material to product. Note: mm steps are required and thBl'E may ha more. than on: solulion to the pmhlam. You may use any addifiunal organic or organumatallic reagents to cffcm your conversions. 1 :i 0 mixture uf mesa and RR. 33 isomers Chemistry 33, Examination 1. Page 13 0/ ----- «m H Good luck! The End ...
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This note was uploaded on 09/24/2009 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at University of California, Berkeley.

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Chem3BFall06PracticeExam2 - EXAMINATION 1 Chemistry 313...

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