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Spectrometric_identification_of_organic_compunds_-_7th_ed_silverstein_2005.pdf andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle 112 CHAPTER 2 INFRARED SPECTROMETRY Problem 2.3 Spectrum A Problem 2.3 Spectrum B Problem 2.3 Spectrum C Problem 2.3 PROBLEMS 113 Problem 2.3 Spectrum D Problem 2.4 Spectrum E Problem 2.4 Spectrum F Problems 2.3 and 2.4 114 CHAPTER 2 INFRARED SPECTROMETRY Problem 2.4 Spectrum G Problem 2.4 Spectrum H Problem 2.4 Spectrum I Problem 2.4 PROBLEMS 115 Problem 2.5 Spectrum J Problem 2.5 Spectrum K Problem 2.5 Spectrum L Problem 2.5 116 CHAPTER 2 INFRARED SPECTROMETRY Problem 2.5 Spectrum M Problem 2.6 Spectrum N Problem 2.6 Spectrum O Problems 2.5 and 2.6 PROBLEMS 117 Problem 2.6 Spectrum P Problem 2.6 Spectrum Q Problem 2.6 Problem 2.6 Spectrum R 118 CHAPTER 2 INFRARED SPECTROMETRY Problem 2.7 Spectrum S Problem 2.8 Spectrum T Problems 2.7 and 2.8 andresfe Rectangle andresfe Rectangle andresfe Line andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle andresfe Rectangle Chapter 8 Additional Problems 1 2.83.03.23.43.63.84.04.24.44.64.8 ppm 45505560657075 ppm 13C/DEPT 1H NMR MASS IR m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 663 1126 1304 1458 2877 3440 10050 50 100 45 63 75 89 107 137 139 200190180170 50 100 16 9 17 1 19 5 19 7 CI Reagent gas methane 13C/DEPT NMR 75.5 MHz 1H NMR 300 MHz 1 Chapter 8 Additional Problems 2 23456789 ppm 20406080100120140160180 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 150.9 MHz % o f B as e Pe ak m/z 10050 0 50 100 41 51 55 65 70 81 83 97 98 111 150140130120110 50 100 113 141 153 m/z CI Reagent gas methane 4000 3000 2000 1000 Wavenumber (cm-1) 80 90 100 % T ra ns m it ta nc e 2954 2931 2870 1712 1458 1149 1103 670680 Hz18701880 Hz 17901800 Hz 390400410420430440 Hz 13C/DEPT NMR 75.5 MHz 1H NMR 300 MHz 2 Chapter 8 Additional Problems 3 4.55.05.56.06.57.07.58.08.59.09.510.010.5 ppm 5060708090100110120130140150160170 ppm MASS 46804700 Hz IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 4120 Hz41804200 Hz4460 Hz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 702 760 1092 1215 1304 1442 1616 1678 2954 3190 1501401301201101009080706050 50 100 53 65 92 120 152 3A Chapter 8 Additional Problems 4 4567891011ppm ppm 4 5 6 7 8 9 10 4 5 6 7 8 9 10 ppm 4567891011 ppm 60 80 100 120 140 160 60 80 100 120 140 160 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz 3B Chapter 8 Additional Problems 5 2.02.53.03.54.04.55.05.56.06.57.0 ppm 2030405060708090100110120130140 ppm MASS IR 1H NMR 600 MHz 3660 Hz41204140 Hz 11201140 Hz 38003820 Hz 13C/DEPT NMR 150.9 MHz % o f B as e Pe ak m/z 1601501401301201101009080706050 50 100 164 149 13112110391 77 65 55 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3514 3016 2935 2850 1597 1512 1427 1265 1153 1034 856 791 4A Chapter 8 Additional Problems 6 2.02.53.03.54.04.55.05.56.06.57.0ppm ppm 2 3 4 5 6 7 2 3 4 5 6 7 ppm 2.02.53.03.54.04.55.05.56.06.57.0 ppm 20 40 60 80 100 120 140 20 40 60 80 100 120 140 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz 4B Chapter 8 Additional Problems 7 ppm 6.06.57.0 ppm 105 110 115 120 125 130 135 140 145 150 3.94.0 ppm 1.81.9 ppm 6.06.57.0ppm ppm 20 30 40 50 3.94.0 ppm 1.81.9 ppm HMQC 600 MHz F1 F2 4C Chapter 8 Additional Problems 8 1.52.02.53.03.54.04.55.05.56.0 ppm 2030405060708090100110120130140 ppm MASS IR 1500 Hz 600620 Hz17401760 Hz % o f B as e Pe ak m/z 15010050 50 100 168 140125 111 97 83 705541 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3078 2924 2854 1643 1466 910 260280 Hz 13C NMR 75.5 MHz 1H NMR 300 MHz 2030405060708090100110120130140 ppm 29.029.229.429.629.8 ppm 13C/DEPT NMR 75.5 MHz 5A Chapter 8 Additional Problems 9 1.01.52.02.53.03.54.04.55.05.56.06.5ppm ppm 1 2 3 4 5 6 1 2 3 4 5 6 ppm 20406080100120140 ppm 1 2 3 4 5 6 1 2 3 4 5 6 F2 F2 F1 F1 COSY 300 MHz HETCO 300 MHz 5B Chapter 8 Additional Problems 10 2.02.53.03.54.04.55.05.5 ppm 2030405060708090100110120130140150 ppm MASS 11001150120012501300 Hz IR % o f B as e Pe ak m/z 140130120110100908070605040 50 100 53 68 77 79 93 107 121 136 4000 3000 2000 1000 Wavenumber (cm-1) 100 % T ra ns m it ta nc e 795 887 1373 1442 1643 2924 3078 85090095010001050 Hz 30.531.0 ppm 1H NMR 600 MHz 13C/DEPT NMR 150.9 MHz 6A Chapter 8 Additional Problems 11 1.52.02.53.03.54.04.55.05.5ppm ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 ppm 1.52.02.53.03.54.04.55.05.5 ppm 20 40 60 80 100 120 140 20 40 60 80 100 120 140 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.61.82.02.2 ppm 20 25 30 35 40 45 ppm 1.61.82.02.2 ppm 1.6 1.8 2.0 2.2 6B Chapter 8 Additional Problems 12 1.41.51.61.71.81.92.02.1 ppm F2 F1 HMBC 600 MHz 4.85.05.25.45.6 ppm ppm 20 25 30 35 40 ppm 4.85.05.25.45.6 ppm 110 115 120 125 130 135 140 145 150 1.41.51.61.71.81.92.02.1 ppm 6C Chapter 8 Additional Problems 13 1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm 406080100120140160180200 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 1134 1211 1288 1373 1450 1612 1682 2870 2924 1501401301201101009080706050 50 100 41 53 67 81 109 123 137 152 13C/DEPT NMR 150.9 MHz 7A Chapter 8 Additional Problems 14 1.01.21.41.61.82.02.22.42.62.83.0ppm ppm 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 ppm 1.01.21.41.61.82.02.22.42.62.83.0 ppm 20 25 30 35 40 45 50 20 25 30 35 40 45 50 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz 7B Chapter 8 Additional Problems 15 F2 F1 HMBC 600 MHz ppm 0.81.01.21.41.61.82.02.22.42.62.8 ppm 150 200 0.81.01.21.41.61.82.02.22.42.62.8ppm ppm 21 22 23 24 25 26 27 28 29 30 31 32 33 ppm 50 52 7C Chapter 8 Additional Problems 16 2.53.03.54.04.55.05.56.06.57.0 ppm 30405060708090100110120130140150160170180 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 42204230 Hz 14101420 Hz36603670 Hz % o f B as e Pe ak m/z 120110100908070605040 50 100 124 109 81 5343 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 3124 2924 1674 1520 1296 1026 802 13C/DEPT NMR 150.9 MHz 8A Chapter 8 Additional Problems 17 2.02.53.03.54.04.55.05.56.06.57.07.5ppm ppm 2 3 4 5 6 7 2 3 4 5 6 7 ppm 2.02.53.03.54.04.55.05.56.06.57.07.5 ppm 20 40 60 80 100 120 140 20 40 60 80 100 120 140 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz 8B Chapter 8 Additional Problems 18 2.32.4 ppm 2.32.4 ppm 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 F2 F1 HMBC 600 MHz 6.26.46.66.87.07.2ppm 6.26.46.66.87.07.2 ppm 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 8C Chapter 8 Additional Problems 19 6.66.76.86.97.07.17.27.37.47.57.67.77.87.9 ppm 120125130135140145150155160165170175180185190195 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 129130 ppm % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 70 80 90 100 % T ra ns m it ta nc e 3286 1635 1597 1442 1281 1149 702 20015010050 50 100 198 121 105 937765 13C/DEPT NMR 150.9 MHz 9A Chapter 8 Additional Problems 20 6.66.87.07.27.47.67.88.0ppm ppm 6.6 6.8 7.0 7.2 7.4 7.6 7.8 6.6 6.8 7.0 7.2 7.4 7.6 7.8 ppm 6.66.87.07.27.47.67.88.0 ppm 115 120 125 130 135 140 115 120 125 130 135 140 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz 9B Chapter 8 Additional Problems 21 ppm 128 130 132 134 136 138 F2 F1 HMBC 600 MHz ppm 6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0 ppm 180 200 6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0ppm ppm 115 120 9C Chapter 8 Additional Problems 22 1.82.02.22.42.62.83.03.23.43.63.84.04.24.4 ppm 406080100120140160180200 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 26802700 Hz % o f B as e Pe ak m/z 140130120110100908070605040 50 100 43 55 69 79 97 140 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 764 1072 1358 1682 1720 2854 2924 25202540 Hz 13C/DEPT NMR 150.9 MHz 10A Chapter 8 Additional Problems 23 2.02.53.03.54.04.5ppm ppm 2.0 2.5 3.0 3.5 4.0 4.5 2.0 2.5 3.0 3.5 4.0 4.5 ppm 2.02.53.03.54.04.5 ppm 20 30 40 50 60 70 80 90 20 30 40 50 60 70 80 90 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.82.02.2 ppm 18 20 22 24 26 28 1.71.81.92.02.1ppm ppm 1.7 1.8 1.9 2.0 10B Chapter 8 Additional Problems 24 ppm 90 100 110 120 130 140 150 F2 F1 HMBC 600 MHz ppm 2.02.53.03.54.04.5 ppm 210 215 2.02.53.03.54.04.5ppm ppm 20 25 10C Chapter 8 Additional Problems 25 1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9 ppm 200 180 160 140 120 100 80 60 40 20 ppm MASS IR 910111213 ppm 13C/DEPT NMR 150.9 MHz 1H NMR 600 MHz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 80 90 100 % T ra ns m itt an ce 949 1188 1404 1705 1728 2962 3178 15010050 50 100 x 204 3 69 71 83 98 11 4 12 5 16 6 16 9 1 84 x64 30.130.2 ppm 30.130.2 ppm 11A Chapter 8 Additional Problems 26 1.01.21.41.61.82.02.22.42.62.83.0ppm ppm 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 1.0 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 ppm 1.01.21.41.61.82.02.22.42.62.83.0 ppm 15 20 25 30 35 40 45 50 55 15 20 25 30 35 40 45 50 55 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.21.41.61.82.02.22.4 ppm 30.0 30.5 11B Chapter 8 Additional Problems 27 0.81.01.21.41.61.82.02.22.42.62.83.03.2ppm ppm 20 25 30 35 40 45 50 55 F2 F1 HMBC 600 MHz ppm 0.81.01.21.41.61.82.02.22.42.62.83.03.2 ppm 180 190 200 210 11C Chapter 8 Additional Problems 28 1.52.02.53.03.54.04.55.05.5 ppm 2030405060708090100110120130 ppm MASS IR % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 100 % T ra ns m it ta nc e 825 980 113413731450 2870 2924 2993 1401301201101009080706050 50 100 53 65 77 79 93 105 121 136 0.91.01.11.21.31.41.51.61.71.81.9 ppm 13C/DEPT NMR 150.9 MHz 1H NMR 600 MHz 12A Chapter 8 Additional Problems 29 1.01.52.02.53.03.54.04.55.05.56.0ppm ppm 1 2 3 4 5 1 2 3 4 5 ppm 1.01.52.02.53.03.54.04.55.05.56.0 ppm 20 40 60 80 100 120 20 40 60 80 100 120 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.01.52.02.5 ppm 15 20 25 30 0.81.01.21.41.61.82.0ppm ppm 1.0 1.5 12B Chapter 8 Additional Problems 30 0.81.01.21.41.61.82.0 ppm F2 F1 HMBC 600 MHz 5.65.7 ppm ppm 16 18 20 22 24 26 28 30 ppm 67 ppm 120 130 140 0.81.01.21.41.61.82.0 ppm 12C Preface Contents Chapter 1: Mass Spectrometry Chapter 2: Infrared Spectrometry Aditional Problems Chapter 2 Chapter 3: Proton NMR Spectrometry Chapter 4: carbon-13 NMR Spectrometry Chapter 5: Correlation NMR Spectrometry; 2-D NMR Chapter 6: NMR Spectrometry of Other Important Spin 1/2 Nuclei Chapter 7: Solved Problems Aditional Problems Chapter 8 Index
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