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sample problems - Chemistry 132CH Final Exam M. E. Jung...

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Unformatted text preview: Chemistry 132CH Final Exam M. E. Jung Page 13 A, 0 (10 points) From the spectroscopic data given, determine the structure of this compound. For partial credit, show your work, i.e., assign peaks in all the spectra as best as you can. Please place your answer on this page. Mass Sectrum m/z 135 105 30 45 60 75 90 120 Chemistry 132BH 2nd Hour Exam M. E. Jung Page 8 8 fi (21 points) A compound, "W', was recently isolated by two hard-working TA’s (and ' researchers) at UCLA. They determined its molecular weight to be 116 and that it contained only carbon, hydrogen and oxygen. It exhibits the IR, 1H and 13C NMR Spectra shown on the next page (the numbers at the top of the NMR spectra are the chemical shifts while the small letters next to the peaks in the proton decoupled 13C NMR spectrum indicate the multiplicities seen in the off-resonance decoupled spectrum). Interpret the spectra and W the structure of the compound. (The page with the spectra on it can be torn out of the exam if it helps you to answer this question, Manlwrite anything of value on that page if you do tear it out!) (8 pts) 21) Interpret the IR spectrum showing the probable types of functionality present. (8 pts) b) Interpret the 1H NMR and 13C NMR Spectra showing the probable types of hydrogen and carbons present (i.e., why they resonate where they do!), their number, and the coupling as well as you can in terms of possible structural features. (5 pts) c) Deduce the structure of "Mambaf, showing your reasoning. Chemistry ISZBH 2nd Hour Exam M. E. Jung Page 9 9. (continued) E g ---———A-— -~————.——_ v- v .- A V__ , , ___ '1 D g I n‘othing g i Q ‘ below 1 : j 4 ppm ‘ " i I ‘ a’ 2 . TMS not I ‘ shown 0 ‘ i g i 3 : ‘ -12.3 "I «‘1' r‘r‘r‘v T‘r'rw ' I I 1 'I fi‘ I' I u—r 1 "1 r r 1-. J 30704 J' 3' ARM “’ 'L" .3; L..__ 5 L 4 g _ l x 2 x . c an», mm 7 t l TMS not S shown F;"""""|" W‘WFMWWWWW‘ ‘1 CU 180 180 140 I:‘(‘ 1(‘(‘ 80 60 40 20 DDM Chemistry 132BH 3rd Hour Exam M. E. Jung Page 8 C} (15 points) Two enterprising persons connected with Chem 132BH isolated a compound from a reaction and named it, " ' They determined its molecular formula to be C9H1002 and took the IR, 1H and 1 C NMR spectra shown on the next page (the numbers at the top of the NMR spectra are the chemical shifts while the small letters next to the peaks in the proton decoupled 13C NMR spectrum indicate the multiplicities seen in the off-resonance decoupled spectrum). When the compound was treated with iodine and sodium hydroxide, a yellow precipitate was formed! From this information, (The page with the spectra on it can be torn out of the exam if it helps you to answer this question, hm 191111 write anything of value on that page if you do tear it out!) NOTE: i.e., analyze the data and state what you learn from each piece of information! 4 ‘ . ‘ ‘ _ x . _ cauwmas puzuusu wCanuoc 3rd Hour Exam Page 9 m waénw w 35.th w v C . /.M w. I. u. Ah . ' u v . u . , . , mason . .7. ILILILIL.E|PIF. ,. 9:... H U. I. B H m m s m g I Maw mm W .m'l” Mb 2. a ma. a CM 8 8 as c.~°u Chemistry 132BH Final Exam M. E. Jung Page 13 v (15 points) Recently chemists at a well known public university in California isolated a compound from a reaction and named it BRUIN. They determined that its molecular weight was 216 and that the molecule contained two chlorine atoms (atomic wt. 35). The IR, 1H and 13C NMR spectra are shown on the next page (the small letters above the peaks in the proton decoupled 13C NMR spectrum indicate the multiplicities seen in the off-resonance decoupled spectrum). You can ignore the information given above the peaks in the proton NMR spectrum; they refer to double irradiation studies. Also the X’s in the proton NMR spectrum indicate impurities in the sample. From the information given on the following page, determine the structure of BRLJIN. (The page with the spectra on it can be torn out of the exam if it helps you to answer this question, W write anything of value on that page if you do tear it out!) NOTE: For partial credit, show your reasoning, i.e., analyze the data and state what you learn from each piece of information! Final Exam Page 14 an“ III- h I“! III. III n Chemistry 1328B 2. . . . wUZ<m¢Omm< ...
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This test prep was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Fall '05 term at UCLA.

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sample problems - Chemistry 132CH Final Exam M. E. Jung...

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