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30bmt1k - Name(Last First MI HQ 2 Student ID Number Circle...

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Unformatted text preview: Name (Last, First, MI): HQ 2) - Student ID Number: Circle your TA: Cait En-Wei June Chem 30B, Fall 2010 Midterm # 1 Monday, October 18 Problem # Possible Points Points'Awarded ***Do not open this exam until instructed to do so*** ***Write all answers in the boxes or spaces provided*** -7 Pages Follow- 1 1. A compound with the formula C9H100 gives the 1H NMR, 13 C NMR, and IR spectra below. Draw the compound in the space provided. 25 points 12 1 1 10 9 8 7’ 0‘ J U! J2: (A I‘\J H C) | H _ HSP-O2-4SS ppm -13C NMR and IR on next page- 200 180 160 140 120 100 80 60 4O 20 0 IZDS— 05—683 mm [DD :7 3 _: E : 50 E p z x x D ”00 3000 20m! 1500 1000 EEO HRVENUHI ERI -nl 2. Below is a hypothetical unsymmetrical molecule. Ha, Hb, and HC are not equivalent to each other and Jab does not equal ch. Draw the splitting one would expect for each set of protons. 15 points Ha Hb Hc —c——c——-c——— Ha Hb Hc 3. The molecule shown below, 4-bromobutyric acid, has a mass of 166. Using structures and/or words, describe the distinctive features and/or fragmentation patterns that you would expect in the mass spectrum of this molecule. 15 points M42 (My?) 04 once ma 3* c M L L A {46/47 r‘e fiVV/Wk’)(’M/w+ How would the fragmentation pattern of the related molecule below be different than 4-bromobutyric acid? 5 points 0 N 0 MC LafiH/Jn] VT (/1 “f” Agf’qu, 4. Below is the 1H NMR spectrum for ethyl vinyl ether. Some of the peaks are blown up so that you can see the splitting. Clearly assign each peak in the boxes provided. 20 points Ha 0 e H \ \/ b (1 He ul- M M» will than» .4, La .47“ .ml . .H 4 , . Eggnnnuw. l hen-AWL, J a _ .4- 5. Below is the IR spectrum of one of the following compounds. Circle the compound. 15 points 100 4000 3000 EDCIIJ 1 50'] 1000 EEO NHVENUI‘IIERI -I| Table lists the wavenumbers in cm'1 and % transmittance Stretching Bmd Frequency (cm'l) Intensity C) — H 3200-3650 weak to strong N-H 3100-3550 medium C—H 2700-3300 weak tomedium C=C 1600-1680 weak tomedium C=0 1630-1820 strong C—O 1000-1250 slrong ‘,R = .Ilk\l. M = Jul) Il(1ll.‘,(‘.l .— RIJHEBI '— R(;H_,1 -- R(2l|_,l)ll-——- .mm— mung -- [((JLF— Arm‘— ' n U |« E Rana”? arm‘— n Ry(:-(‘llk.__— Rt:==(:u 19("(1113— urn—«mam: 0 Ni“— :(iu‘m ii RH”!— RCUCHJI (">7 V, ('hcmix .ll Shift If!) (I) () mkfin. ml}; 1R:;\H\\l‘¢ o R R(X)II 0 R‘(X)ll——-—-—- \ 1 _ U Ri'NR; mum —..__.._ ;‘ Raga—~— R(.()R [u ”,5. ———- 1 \' Rx(j[l-_— é \ ILA-R , nun; _ T k:(;_,(:|(_‘— R( llv“—— , R( =1 R—'——— R(‘H.‘-_— [( ”UI‘S‘ i J 200 [MI 1130 110 12(1 10” ml 60 10 20 II ppm (.hcmiml Shift 16) '“c-rsm‘ ...
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