Interpretação de Espectros IR-Massa-NMR Problemas Resolvidos

Problem 67 IR Spectrum liquid film 3420 1742 4000 3000 2000 1600 1200 800 V cm¹ Mass Spectrum 31 45 61 76 M 104 1 C₄H₈O₃ No significant UV absorption above 220 nm 40 80 120 160 200 240 280 me ¹³C NMR Spectrum 500 MHz CDCl₃ solution DEPT CH₂ CH₃ CH proton decoupled solvent 200 160 120 80 40 0 δ ppm ¹H NMR Spectrum 200 MHz CDCl₃ solution expansions exchanges with D₂O 44 40 36 ppm 14 12 ppm TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 156 Problem 68 IR Spectrum liquid film 2266 1749 4000 3000 2000 1600 1200 800 V cm¹ Mass Spectrum 68 86 M 113 C₅H₇NO₂ No significant UV absorption above 220 nm 40 80 120 160 200 240 280 me ¹³C NMR Spectrum 500 MHz CDCl₃ solution DEPT CH₂ CH₃ CH proton decoupled solvent 200 160 120 80 40 0 δ ppm ¹H NMR Spectrum 200 MHz CDCl₃ solution expansions TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 157 Problem 69 IR Spectrum liquid film 3428 1714 4000 3000 2000 1600 1200 800 V cm¹ Mass Spectrum 45 43 73 M 88 C₄H₈O₂ No strong UV absorption above 220 nm 40 80 120 160 200 240 280 me ¹³C NMR Spectrum 500 MHz CDCl₃ solution DEPT CH₂ CH₃ CH proton decoupled solvent 200 160 120 80 40 0 δ ppm ¹H NMR Spectrum 200 MHz CDCl₃ solution expansions exchanges with D₂O 45 40 ppm 20 15 ppm TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 158 Problem 71 IR Spectrum liquid film 4000 3000 2000 1600 1200 800 1740 V cm1 Mass Spectrum No significant UV absorption above 220 nm of base peak 20 40 60 80 100 me 40 80 120 160 200 240 280 M 116 1 C6H12O2 13C NMR Spectrum 100 MHz CDCl3 solution DEPT CH2 CH3 CH solvent proton decoupled 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 100 MHz CDCl3 solution 385 ppm 192 ppm 093 ppm expansions at 400 MHz 10 9 8 7 6 5 4 3 2 1 0 δ ppm 160 Problem 96 IR Spectrum liquid film 4000 3000 2000 1600 1200 800 V cm1 Mass Spectrum UV Spectrum λmax 260 nm log10 ε 25 of base peak 20 40 60 80 100 me 40 80 120 160 200 240 280 M 134 C10H14 13C NMR Spectrum 1000 MHz CDCl3 solution DEPT CH2 CH3 CH proton decoupled solvent 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 400 MHz CDCl3 solution expansions 75 73 ppm 28 27 ppm 18 17 ppm 145 135 ppm 105 095 TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 185 Problem 106 IR Spectrum liquid film 4000 3000 2000 1600 1200 800 1760 V cm1 Mass Spectrum UV Spectrum λmax 265 nm log10 ε 26 λmax 271 nm log10 ε 26 solvent methanol of base peak 20 40 60 80 100 me 40 80 120 160 200 240 280 M 150 C9H10O2 13C NMR Spectrum 1000 MHz CDCl3 solution DEPT CH2 CH3 CH expansion 24 20 ppm expansion 24 20 ppm solvent proton decoupled 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 400 MHz CDCl3 solution expansion 72 70 ppm TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 195 IR Spectrum liquid film 1724 V cm1 Problem 107 Mass Spectrum C9H10O2 UV Spectrum λmax 238 nm log10ϵ 42 λmax 281 nm log10ϵ 27 solvent methanol 13C NMR Spectrum 1000 MHz CDCl3 solution expansion 1325 1300 ppm DEPT CH2 CH3 CH expansion 1325 1300 ppm solvent proton decoupled 1H NMR Spectrum 400 MHz CDCl3 solution expansion 80 79 73 72 ppm TMS δ ppm 196 IR Spectrum liquid film 1712 1277 1254 V cm1 Problem 127 Mass Spectrum C11H14O3 UV Spectrum λmax 257 nm log10ϵ 43 solvent methanol 13C NMR Spectrum 500 MHz CDCl3 solution DEPT CH2 CH3 CH proton decoupled solvent 1H NMR Spectrum 200 MHz CDCl3 solution expansions 46 42 38 ppm 16 12 ppm TMS δ ppm 216 IR Spectrum KBr disc 1689 V cm1 Problem 159 Mass Spectrum C10H11BrO2 UV Spectrum 13C NMR Spectrum 500 MHz CDCl3 solution one signal even at high field DEPT CH2 CH3 CH Resolves into two signals at higher field proton decoupled solvent 1H NMR Spectrum 200 MHz CDCl3 solution expansions exchanges with D2O 82 80 78 76 ppm 110 100 31 30 29 ppm 14 13 12 ppm TMS δ ppm 248 Problem 165 IR Spectrum liquid film 4000 3000 2000 1600 1200 800 V cm1 1685 Mass Spectrum UV Spectrum λmax 225 nm log10ε 39 solvent methanol 68 M 96 C6H8O 40 80 120 240 280 me 13C NMR Spectrum 1000 MHz CDCl3 solution DEPT CH2 CH3 CH proton decoupled solvent 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 400 MHz CDCl3 solution expansions expansions 69 68 ppm 590 585 ppm 24 22 ppm 19 18 ppm TMS 10 9 8 7 6 5 4 3 2 1 0 δ ppm 254 Problem 192 IR Spectrum liquid film 4000 3305 3000 2000 1600 1200 800 V cm1 Mass Spectrum No significant UV absorption above 220 nm 45 59 M 74 1 C4H10O 40 80 120 160 240 280 m e 13C NMR Spectrum 500 MHz CDCl3 solution proton coupled solvent proton decoupled 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 200 MHz CDCl3 solution expansion exchanges with D2O TMS 35 25 ppm 10 9 8 7 6 5 4 3 2 1 0 δ ppm 281 Problem 208 IR Spectrum liquid film 4000 3000 2000 1600 1200 800 V cm1 Mass Spectrum UV Spectrum λmax 250 nm log10ε 40 103 77 M 182184 C8H7Br 40 80 120 160 200 240 280 me 13C NMR Spectrum 500 MHz CDCl3 solution CH 2x CH expansion CH CH proton decoupled C solvent 135 130 ppm 200 160 120 80 40 0 δ ppm 1H NMR Spectrum 200 MHz CDCl3 solution expansion 80 70 60 ppm 10 9 8 7 6 5 4 3 2 1 0 δ ppm 297 Problem 261 IR Spectrum liquid film V cm1 Mass Spectrum C5H10O UV spectrum 495 mg 10 mls path length 100 cm solvent hexane 13C NMR Spectrum 200 MHz CDCl3 solution proton decoupled solvent TMS 1H NMR Spectrum 100 MHz CDCl3 solution expansion of 400 MHz spectrum TMS Problem 278 An organic compound has the molecular formula C10H14 Identify the compound using the spectroscopic data given below vmax liquid film no significant features in the infrared spectrum λmax 265 log e 23 nm 1H NMR CDCl3 solution δ 71 m 5H 25 apparent sextet J 7 Hz 1H 16 apparent quintet J 7 Hz 2H 122 d J 7 Hz 3H 081 t J 7 Hz 3H ppm 13C1H NMR CDCl3 solution δ 1484 C 1293 1279 1261 423 CH 317 CH2 222 122 CH3 ppm Mass spectrum me 134 M 20 1198 105100 7710 Problem 279 An organic compound has the molecular formula C12H17NO Identify the compound using the spectroscopic data given below vmax KBr disc 3296m 1642s cm1 1H NMR CDCl3 solution δ 723742 m 5H 574 br s exch D2O 1H 514 q J 67 Hz 1H 215 t J 71 Hz 2H 166 m 2H 148 d J 67 Hz 3H 093 t J 73 Hz 3H ppm 13C1H NMR CDCl3 solution δ 1720 C 1433 C 1286 1273 1261 485 CH 388 CH2 217 CH3 191 CH2 137 CH3 ppm Mass spectrum me 191M 40 12033 10558 104100 7718 4346