F07 quiz2

F07 quiz2 - Mamas/7i Clzazleijec, PhD. Chem 308 ~Fall 2007...

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Unformatted text preview: Mamas/7i Clzazleijec, PhD. Chem 308 ~Fall 2007 Student ID Number : Signature Name Of‘yOm-TA‘ Melanie / Eric / Robert /€hris (Please Cn‘cle) r ya. nymsawspa H AVE: 3‘. ‘4 ~ ‘ ‘v‘: .‘ -:€>‘T~ :5: "n r15" ‘ L .x: :w,m‘~.r‘»-. g: ,¢r..-‘L‘:ir'r g Hiswssion Sectian — Jay : Time: L 2::7: g», a " 816111 30 B Fall 2067 Qaiz # iii {35% 1:; Friday Navembar 99 2%7 P ‘ S 2 ,1 2 .5 As Se Sb Te DO NOT OPEN THIS EXAM UNTIL INSTRU€TED TO DO SO iii/{CIHCZS/li Clzaneljjee, PILD. Chem 303 —Fall 2007 E. [5 points each] In each problem below, choose 0 , d (optical activity, MS, IR, ill NM’R, or 13C NMR) that will al low you t unambiguously istinguish between the two compounds. Precisely describe the difference t a y u expect to see in the spectra of the two compounds that will allow you to distinguish between the compounds (correct description of the difference in the spectra is worth 3 points). Be brief (no more than two sentences). Method for distinguishing A from B: 9H I m 0‘ H NMR _ 1 l \\ \ Reason: A has 2- ‘5 I iii/K/ / dared f5 hasslinzflhéwb'cgts~ 3 Cl compound A compound B Nor P055; b1: 60 an: hiya/sh c!- D {-»——~mm——. -- .. __ w [.Hq am V, @ Method for distinguishing C from D: 'L /\\ OH OH \ (i ’ \ \\/// ' / no chiral can?" compound (‘ compound D Method for distinguishing E from F: OH OH ! 1 l Mass. ) Bmmu / \ I “"" isotope); E! Reason: Q Mfg. I ’ + 2. MM wt lil‘ cl” l l ‘ ————~————————Z@— lama ’ c1 : —— / C" Br I MfL.L 3%) woke/33w - "10/1 WP wv ll be Iowa r— fyompjanj E compound : “J. .r V 7.27.7, - x x_ ' v lg) Mamas/7i Charter/ea, P/1.D. C6 12 O Chem 301? —Fall 2007 Ont one deg, 09 unsatuml-im ( / TLbond (=0 (=6. 2, [20 points] Deduce the stmcture of the unknown compound with molecular formula 04 Mn ~ ammo from the data given below. 1“C has CBCI3 signals at 77 ppm. Clearly label the 3/) Protons and the Carbons 0n the spectrum and on your structure (use a—e and 1-6). You must show work to get full credit. \ — H m 5 5 0‘ O H Ha t” l” l ‘ céHuo ' H “9/ ' 6P¢aK$ h b rl H ‘ - H b “A H,” HL H Ht, 0' L; :H " g m, 2H m, 2H ' I V b PH ' fey”: ’7 3 /'/“ [in ’ at <1 z —- 57> -> r its“ WmkvhifiilpjjvlflxL#Ulv‘mngflgwl,J‘HL, __,,A_ v ‘ *A— r no C-“ Protons. 2,. no C 1C 13(1lxllWRploton decoupled CGHnO {.5 a”? P Information from 13C NMR ,. O '5 6 (quarkvnavg) % \ , 2,10 m )l \ i c a»? /c, O @ PF g h f \‘N' l C P a 2. s e633 1 ‘ cl L * “9/2 '5 l3 / x t F wwwWWWWW T} ‘ ‘ (Q '5) Csfluo é Soucture of unknown: (16‘) C”: 3 W o 100 5f ., 3 ...
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F07 quiz2 - Mamas/7i Clzazleijec, PhD. Chem 308 ~Fall 2007...

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