Quiz_2 solutions

Quiz_2 solutions - Chemistry 124/224 UC Santa Barbara...

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Unformatted text preview: Chemistry 124/224 UC Santa Barbara Winter Quarter, 2008 Quiz # 2 (2/07/08) 1. Select appropriate structure(s) for the following spectra (3 pt x 2) Spectrum A Spectrum B ML J 4“ M “KH—— —~” VJ“ .__—____—.b— -i— I | l ' 1 I ' l ' l 7155 7'30 1:” 75;, 7’35 73:, ppm 3.20 X.|8 M6 M4 M2 ppm 7.56 7154 732 7150 7.11% ppm No2 Cl N02 fl ri\' Br 7‘) I , B 5 fl “‘ A °( 1 CI Cl N02 D E F 2. Explain the two doublets in the spectrum for CH3-C0-CH2F (3 pt) 3V“- ;v‘~ \‘V\ "F (xv/)Hwi 0 1C: w: ((32% i 48H \ J A J 7‘ “ac CPU: 4.3 H7. H V 1 S K ‘ ' 660 658 656 654 652 Hz Page 2 3. The top spectrum is the 1H NMR for cellobiose octacetate prepared using a spatula. Explain Why you have broad fines and how you can get the decent bottom spectrum. (3 pt) 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 sec 7 6 5 4 3 2 ppm memmeWmWTfiW FfifwaWWW 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 sec 7 6 5 4 3 2 ppm \‘v’m‘u’ (CMqu it. ‘01“pr r“: X \{ ‘. (b.9323 »/ w’q SL4: / 5L (9 \c‘-~7dc-~'¥<};w "Wk 1 \ :1 Wm / 52th L2 L\ Page 3 4. Explain why annulene has a negative proton chemical shift and a downfield chemical shift. (3 pt) 6 9.3 ppm Q: LQVVV :> (kHz-ANA. : C (I. “ ) {kw-X LV‘G/(vxlr' \E lbé “Alida A)“ ‘a r"\ 5. Answer the spin systems for the following compounds? (2 pt x 8) A. CHzClz B. CH2=C12 C. CH2=CF2 V- - l l . i A?- “L M wt x D. MeOOC—CHz—CHZ-COOMe E. MeOOC—CHz-CHz—CHz-COOMe A L? F. MeOOC—CH2~CH2—CH2-CH2—COOMe AZAZXLXZ G. /—\ 1. Two oxymethylenes O O ( v N'\ Rig Am 2. Phenyl group AA' 3% ’ a. Page 4 6. Get the structures from the 'H and 13C NMR spectra. (7 pt x 2) (the numbers underneath the proton spectra represent the number of proton) A. MF: CSHMO4 61 253 13.566 3.461 46 092 1 170.095 200 180 16!] 14!] 12B 100 80 ED 40 20 ppm I f; _L 1 L I I 1‘ rl' l' l I l l V r—l—Ifi F I-“r—T—l—T I‘lfi—T—fl—Yfir—Tj 10 9 a 7 6 V 5 4 3 2 1 ppm H-’ ‘—r_' n..,._n_r._- 4.10 3.0“ 1.01 5.39 0N1? «\K ’ \ C3 a s. or » cufc‘ufo J\ \ fix) ‘ V m)- Chg—“0“” , caucus z: v \ 5 a LJ B.MF:C7H5NO4 N 0 cm a! N com ~ w. '3“. s; E a :3 l 4 E g / \ a: 2 ~ 3 \ l 1 « . mm”, ‘ . x 200 18!] 160 140 120 100 BD 50 40 20 ppm g." l 3.1 7.9 7.7 7.5 7.3 ppm .1 ._|—______.— m I I l f-T—T-T r_'_r—l—| r—l I I r‘| I! 12 11 10 9 8 7 a 5 a 3 2 1 ppm Lr—I ‘—r—J L—w—J l—r—’ 0.52 1.05 0.88 2.14 omsa 0 Lip/0 \/ ‘ >\\\4 90; / X" 71?.“ f \ 1 UMQ, \ \ \\\ “OH 5 ‘ 7, i“! . /1V —)\§C «W\ Hc 1 2. NO 2 t" » ; 1 x .I' “A Page 5 ...
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This note was uploaded on 08/06/2008 for the course CHEM 124 taught by Professor Amagata during the Winter '08 term at UCSB.

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Quiz_2 solutions - Chemistry 124/224 UC Santa Barbara...

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