spec quiz answer key sp08

spec quiz answer key sp08 - Organic Chemistry 2 CHM U313...

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Unformatted text preview: Organic Chemistry 2 CHM U313 Spectroscopy Quiz ' , 1/29/08 . Name WEI—(L [CE ; Multiple choice problems #3-10: write the capital letter corresponding to the best answer above the line at the start of the question Questions are worth 5 points unless otherwise indicated. Useful info for mass spectrometry: atomic masses: C = 12, H = I, O = 16, 7E'Br = 79, “Br = 81; group masses: CH3 = 15, CZHS = 29, C3H7 = 43, C411, = 57, CSH11 = 71, CGH13 = 85 ‘ 1. (8 points) Which C7HHO ketone A-C (mol. wt. 114) gave the mass spectrum shown below? Explain briefly, based on expected fiagmentation patterns and focusing on the peaks labeled with a number. ' jet/(5’ M'w M’l‘l M'L/J 111/2 71 (swwd Kb Wig ('3' M/2 *3 M/z 35‘ (I? § pemx Q Ci H - QCHZCH2CH2CH3 CH3CH - 7 . ' Cfisflfizmzc .H20H2CH3 MT ’ C ‘ 317.0”) ' A , ’C 1 common Grdjmdf‘t‘ovx 4Q” éefll’mLS ,‘ ’04) , « + High “‘37 P’CFEC‘): r R: B 5M5 MW 3"“ 6V /0$S o F 74”" A WA 9, M4. Small, 80 m O 40. 7 Q’s,“ Relative Intensity 20 if it 25 so 75 100 125 4 [c n —>iC I M51424; «Curl/zit MM 7M 51>} (5 23C, CH3 CH) \fijdf‘ WA hath 2. (8 points) Haloalkane _, especially 1° RX, tend to give a lot of fiagment ions in mass spectra. For the belowof Lbromopentane, CH3CH2CH2CH2‘CH2Br '(M = 150, M+2 = 152), assign the origin of each of the ion peaks labeled with avnumber as arising fi‘om either cit-cleavage, heterolyfic cleavage, or ordinary hydrocarbon cleavage. ‘ , have“ {7 2 ; I (7} d ,1; I I ’ discftxqu‘lfl; 1.’ V f ' Acgfifl ’qp' ' yin/.2 71 100 on O G) 0 Relative lntensit y A 0 “7mm” mess; ,vw/X (/oss Mr FM”) :2e7 its/Z Mp)“ M W/Z Calf/UK (mm; or Err, cewlfatcgg 20 25 SO 75 100 125 150 L) 3. Which of the given compounds corresponds to the IR spectrum shown below? —_.._._..— M K“ M km; 3300 M M paw c: M vgopgefdjflm CH3CH2CH2CH§CH20H CH30H20H2CHZCH2CEN CH3CHZCH2CHgCH2CH=CH2 M0 C7C - A B c . CH;CH2CH2CH2CH2CECH CHSCHZCHZCHZCHZOCHE’ \ he 5”va (’0 9% D , EC em - viaW‘ON) 5w 39 100 u a d g g I c:- ‘ .. :a mm s O ms: 696: 99s: A A \J LED 'Wavenumbers (c3114) C 4. Which of the given compounds corresponds to the IR spectrum shown belowztg b M ( o—woo bark an,” N "w w: 3W3 “OWL / C Me 0 / o o o ' o u n n I u u CHgCHZCOH CH3CHZCOCH3 CH3CHZCH CHgCH2CNH2 CH3CH2CCH3 ’ A - B 7 C . ~ ' D E LDD rmsm rrmzl a. 9 “U 3 5. (4 pts) How many signals would you expect to see in the 1H NMR spectrum of the following compound? . HZC’EZC E N H \ 1 , fl“ gym A)2 B)3 C)4 D)5 E)6 F)7 G)8 C 6. Which CgHgBr isomer gave the following ‘H NMR spectrum? 5W9. a O 2: 3 CH2CH3 2 r‘ L Br ( 7 3 CHs \ CH2CHzBl' \CHCH3 ’5, L w: A 7. Which C‘gl-IuO2 isomer gave the following 1H spectrum? I 6‘ 7‘yflM watt fix/r5 “1° twig 9+7!“ ‘3 ‘3; if ‘3 CH3CH2COC~HZCH2CH3 CH3CH20CCH2CH2CH3 CH3CH20CCH(CH3)2 ‘ CH3CH2COCH(CH3)2 D 8. For the type of proton indicated in bold, What is the simplest multiplet pattern that you would expect in a 1H NMR spectmm? A sinlet B) doublet C) triplet l f ~ E) quintet F) sextet CH3$°CH2CH2?CH3 septet H) > septet H k4" H . ‘ «(e b 9. Which CSHIOO isomer gave the following iHNMRspectrum? MS “:3‘7‘ H) we see? W W CH3CCH2CH2CH3 CH3CH2CH2CH2CH CH3C'HCCH3 CH3CIIHCH28H ’ CH3CH2(IJHCH‘ CH3 CH3 D CH3 A B C amid L 7 MW: ' ‘ * (Elle,- [EAR y‘éC/Q) 5.0 4.5 4.0 3.5 3.9 2.5 \fl: 16:” 1W0.:L&AVA> [if “L 10. Which CgH. O isbmer rave the follo ' 1H NMR 3 ctrum? C(JV‘J‘Lj ____.. 12 g , wmg pe (ER my CH CH CH ' _ . 2 2 m~CHCH2CH3 HO CHCH3 CPIZCH20CH3 CHZOH CH3 CH3 CHgCH; A B C D ' E B 5 3 2 1 O W 6 4 @k’O’W W/Afi Mai/#1 C435 ...
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spec quiz answer key sp08 - Organic Chemistry 2 CHM U313...

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