Baixe Silverstein Capítulo 08 - Resolução e outras Exercícios em PDF para Química, somente na Docsity! 1.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm 406080100120140160180200 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 110100908070605040 50 100 41 55 68 84 97 112 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 856 941 1161 1342 1454 1701 2858 2927 13C/DEPT NMR 75.5 MHz 1H NMR 300 MHz O Cycloheptanone C7H12O Mol. Wt.: 112 1 2 3 4 2 4 3 1 2 4 3 Problem 8.1 CHAPTER 8 ASSIGNED PROBLEMS 3.54.04.55.05.56.06.57.07.5 ppm 405060708090100110120130140150160170180190 ppm 13C/DEPT 1H NMR MASS 21402150 Hz IR 19501960 Hz 19201930 Hz 1201101009080706050 50 100 124 95 94 816653 % 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 3398 3005 2947 2839 1601 1493 1284 1149 1041 945 837 768 687 13 / NMR 75.5 MHz 1 300 MHz OH 2 4 5 1 7 3 7 2 4 1 5 6 3 OH OCH3 m-Methoxyphenol C7H8O2 Mol. Wt.: 124 1 2 3 4 5 6 7 Problem 8.2 CHAPTER 8 ASSIGNED PROBLEMS 2.53.03.54.04.55.05.56.06.57.07.5 ppm 405060708090100110120130140150160170180190 ppm 13C/DEPT 1H NMR MASS IR 21202140 Hz22802300 Hz % o f B as e Pe ak m/z 130120110100908070605040 50 100 39 43 49 57 83 111 126 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3089 1662 1415 1273 1061 933 856 725 590 13C/DEPT NMR 75.5 MHz 1 300 MHz m/z %M 126 (M) 100.0 127 (M+1) 8.2 128 (M+2) 4.9 S O CH3 Ethanone, 1-(2-thienyl)- 2-Acetylthiophene C6H6OS Mol. Wt.: 126 1 2 3 4 5 6 1 6 2 4 5 3 1 6 2 4 5 3 Problem 8.5 CHAPTER 8 ASSIGNED PROBLEMS 2.53.03.54.04.55.05.56.06.57.07.5 ppm 30405060708090100110120130140 ppm MASS 2200221022202230224022502260 Hz 157015801590 Hz IR 1H NMR 300 MHz 13C/DEPT NMR 75.5 MHz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 70 80 90 100 % T ra ns m itt an ce 594 694 764 964 1211 1450 1496 2985 3032 15010050 50 100 x 10 51 77 105 184 186 620630640 Hz H3C Br (1-Bromoethyl)benzene C8H9Br Mol. Wt.: 184 1 2 3 4 5 6 6 2 4 5 3 1 6 2 4 5 3 Problem 8.6 CHAPTER 8 ASSIGNED PROBLEMS 3.54.04.55.05.56.06.57.0 ppm 5060708090100110120130140150 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 1201101009080706050 50 100 53 63 75 81 109 124 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 3348 2951 2835 1859 1701 1612 1512 1234 1034 825 733 513 1 300 MHz 13 / NMR 75.5 MHz OH OCH3 p-Methoxyphenol C7H8O2 Mol. Wt.: 124 1 2 3 4 5 2 5 3 OH 1 2 4 5 3 Problem 8.7 CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.5 ppm 2025303540455055606570758085 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 100 % T ra ns m itt an ce 3344 2958 2931 2873 1466 1331 1045 849 1201101009080706050 50 100 54 67 84 93 111 126 78808284 ppm 1H NMR 300 MHz 13C/DEPT NMR 75.5 MHz OH 3-Octyn-1-ol C8H14O Mol. Wt.: 126 12 3 4 5 67 8 1 7 6 2 5 8 OH 1 7 6 2 4 5 3 8 Problem 8.10 CHAPTER 8 ASSIGNED PROBLEMS 5.25.45.65.86.06.26.46.66.87.07.27.4 ppm 115120125130135140145150155 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 1601501401301201101009080706050 50 100 63 73 98 126 128 162 164 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 555 725 814 1188 1277 1404 1477 1585 3097 3521 1H NMR 300 MHz 13C/DEPT NMR 75.5 MHz Problem 8.11 Cl OH Cl 2,4-Dichlorophenol C6H4Cl2O Mol. Wt.: 162 1 2 3 4 5 6 6 5 3 OH 1 6 2 4 5 3 CHAPTER 8 ASSIGNED PROBLEMS 3.03.54.04.55.05.56.06.57.07.58.0 ppm 405060708090100110120130140150160170180190 ppm MASS IR -104.4 -104.5 ppm 19F NMR 282.4 MHz 118120122124126128130 ppm % o f B as e Pe ak m/z 1401301201101009080706050 50 100 138 123 95 75 6350 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 3356 3074 3005 1685 1597 1358 1265 1157 960 841 567 238023902400 Hz 21302140 Hz 1H Decoupled 1H Coupled 13C/DEPT NMR 75.5 MHz 1H NMR 300 MHz COCH3 F 4-Fluoroacetophenone C8H7FO Mol. Wt.: 138 1 2 3 4 65 1 6 2 4 5 3 6 2 3 Problem 8.12 CHAPTER 8 ASSIGNED PROBLEMS 2.22.32.42.52.62.72.82.93.03.13.23.33.43.53.6 ppm 2030405060708090100110120 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 70 80 90 100 % T ra ns m itt an ce 756 1250 1435 2245 2970 1501401301201101009080706050 50 54 68 79 81 93 95 107 109119 121 147 149 13 / NMR 75.5 MHz 1 300 MHz Br N 4-Bromobutanoyl nitrile C4H6BrN Mol. Wt.: 147 1 234 2 4 3 1 2 4 3 Problem 8.15 CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm 405060708090100110120130140 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 1401301201101009080706050 50 100 77 106 137 4000 3000 2000 1000 Wavenumber (cm-1) 80 90 100 % T ra ns m itt an ce 825 1049 1442 1512 1620 2931 3194 3348 2345 ppm 13 / NMR 75.5 MHz 1H NMR 300 MHz NH2 OH p-Aminophenylethanol C8H11NO Mol. Wt.: 137 1 2 3 4 5 6 1 6 2 4 5 3 OH 6 2 5 3 OH Problem 8.16 CHAPTER 8 ASSIGNED PROBLEMS 6.26.36.46.56.66.76.86.97.07.17.27.37.47.57.6 ppm 110115120125130135140145150155160165 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 1201101009080706050 50 100 119 91 76 64 4000 3000 2000 1000 Wavenumber (cm-1) 70 80 90 100 % T ra ns m it ta nc e 3309 2245 1589 1481 1342 787 671 13 / NMR 75.5 MHz 1H NMR 300 MHz N OHC p-Cyanophenol C7H5NO Mol. Wt.: 119 1 2 3 45 2 3 OH 1 2 4 5 3 Problem 8.17 CHAPTER 8 ASSIGNED PROBLEMS 2.53.03.54.04.55.05.56.06.57.0 ppm 406080100120140160180 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 120110100908070605040 50 100 123108 8053 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 3109 2947 1651 1404 1095 741 633 2060 Hz 1820 Hz2020 Hz 13 / NMR 75.5 MHz 1H NMR 300 MHz 1 7 6 2 4 5 3 7 2 4 5 3 N H3C O CH3 1-Methyl-2-acetylpyrrole C7H9NO Mol. Wt.: 123 1 2 3 4 5 6 7 Problem 8.20 CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.5 ppm 406080100120140160180200 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 150 50 100 187 159 15010050 50 100 x 20 158103 85 57 43 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 2962 1720 1651 1319 1149 1034 CI Reagent gas methane m/z 13C/DEPT NMR 75.5 MHz 1 300 MHz O OO Isobutylacetoacetate C8H14O3 Mol. Wt.: 158 1 2 3 4 5 6 7 7 1 7 6 5 3 1 7 6 2 4 5 3 Problem 8.21 CHAPTER 8 ASSIGNED PROBLEMS 6.26.36.46.56.66.76.86.97.07.17.27.37.4 ppm 115120125130135140145150155 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 1201101009080706050 50 100 119 91 76 64 4000 3000 2000 1000 Wavenumber (cm-1) 70 80 90 100 % T ra ns m itt an ce 3309 2245 1589 1481 1342 787 671 13C/DEPT NMR 75.5 MHz 1 3 N OH C m-Cyanophenol C7H5NO Mol. Wt.: 119 1 2 3 4 5 6 7 1 7 6 2 4 5 3 6 2 4 5 OH Problem 8.22 CHAPTER 8 ASSIGNED PROBLEMS 2.02.53.03.54.04.55.05.56.06.57.0 ppm 5060708090100110120130140 ppm MASS IR 1H NMR 300 MHz 13C/DEPT NMR 75.5 MHz 20402050 Hz 605610615 Hz10801090 Hz % o f B as e Pe ak m/z 9080706050 50 100 51 66 91 92 9080 50 100 93 CI Reagent gas methane 4000 3000 2000 1000 Wavenumber (cm-1) 80 90 100 % T ra ns m itt an ce 725 802 1065 1342 1720 2962 3055 m/z Bicyclo[2,2,1] hepta-2-5-diene C7H8 Mol. Wt.: 92 12 3 1 2 3 1 2 3 Problem 8.25 CHAPTER 8 ASSIGNED PROBLEMS 5.956.00 ppm 105110115120125130135140145150155 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 1601501401301201101009080706050 50 100 63 98 121 156 158 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 586 802 933 10411234 1473 2900 6.656.706.756.806.85 ppm 13C/DEPT NMR 150.9 MHz M M+2 O O Cl 5-chloro-1,3-benzodioxole C7H5ClO2 Mol. Wt.: 156 1 2 3 4 5 6 7 1 7 6 2 4 5 3 7 6 4 3 Problem 8.26 CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.54.0 ppm 405060708090100110120130140150160170 ppm 13C/DEPT 1H NMR MASS IR % o f B as e Pe ak m/z 110100908070605040 50 100 42 55 70 84 114 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 571 856 1057 1165 1442 1728 2931 13 / EPT NMR 75.5 MHz 1 300 MHz O O ε-Caprolactone C6H10O2 Mol. Wt.: 114 12 3 4 5 6 1 6 2 4 5 3 1 6 2 4 5 3 Problem 8.27A CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.5ppm ppm 1.5 2.0 2.5 3.0 3.5 1.5 2.0 2.5 3.0 3.5 ppm 1.52.02.53.03.5 ppm 25 30 35 40 45 50 55 60 25 30 35 40 45 50 55 60 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.41.61.82.0 ppm 32 33 HO Cl 1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136 1 2 3 4 5 6 1 6 2 4 5 3 OH 1 6 2 4 5 3 OH Problem 8.28B CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.54.04.55.0 ppm 2030405060708090100110120130 ppm 13C/DEPT 1H NMR MASS 1540 Hz 1140 Hz IR % o f B as e Pe ak m/z 1301201101009080706050 50 100 45 55 67 69 81 95 110 113 128 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m it ta nc e 825 1041 1126 1377 1450 2924 2966 3344 440 Hz480500 Hz 13 / EPT NMR 75.5 MHz 1 300 MHz 6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128 OH 1 2 3 4 5 6 7 8 1 7 2 4 5 3 8 OH 1 7 6 2 4 5 3 8 Problem 8.29A CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.55.05.5ppm ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 ppm 20406080100120 ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 F2 F2 F1 F1 COSY 300 MHz HETCO 300 MHz R 75.5 MHz 6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128 OH 1 2 3 4 5 6 7 8 1 7 2 4 5 3 8 OH 1 7 2 4 5 3 8 OH Problem 8.29B CHAPTER 8 ASSIGNED PROBLEMS 4.85.05.25.45.65.86.06.26.46.66.87.07.27.4 ppm 708090100110120130140150160 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 130120110100908070605040 50 100 41 65 77 91 94 105 119 134 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 690 752 1242 1496 1601 2866 2916 3032 3066 36603680 Hz 32803300 Hz 32003220 Hz 27402760 Hz 13 / P 150.9 MHz OCH2CH=CH2 Allylphenyl ether C9H10O Mol. Wt.: 134 1 2 3 4 5 6 7 1 7 6 2 4 5 3 7 6 2 4 5 3 Problem 8.31A CHAPTER 8 ASSIGNED PROBLEMS 4.55.05.56.06.57.07.5ppm ppm 4.5 5.0 5.5 6.0 6.5 7.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm 4.55.05.56.06.57.07.5 ppm 70 80 90 100 110 120 130 140 150 70 80 90 100 110 120 130 140 150 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz OCH2CH=CH2 Allylphenyl ether C9H10O Mol. Wt.: 134 1 2 3 4 5 6 7 7 6 2 4 5 3 1 7 6 2 4 5 3 diastereotopic Problem 8.31B CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.54.0 ppm 15202530354045505560657075 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 2400 Hz 1150 Hz1350 Hz 550 Hz750 Hz950 Hz1050 Hz 500 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 3317 2951 2877 1712 1365 1227 1057 829 1501401301201101009080706050 50 100 x 20 154139 136121 110 109 95 6755 13 / P 150.9 MHz In the above insets each tick mark is 10 Hz OH CH3 H3C CH3 Borneol C10H18O Mol. Wt.: 154 1 2 345 6 7 8 910 3 6 6 2 4 5 3 8 9 10 OH 1 7 6 2 4 5 3 8 9 10 5 3 Problem 8.32A CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.5ppm ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 1.0 1.5 2.0 2.5 3.0 3.5 4.0 ppm 1.01.52.02.53.03.54.04.5 ppm 10 20 30 40 50 60 70 80 10 20 30 40 50 60 70 80 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.52.02.5 ppm 28 30 O O γ-Caprolactone C6H10O2 Mol. Wt.: 114 1 23 4 5 6 3 6 2 4 5 3 6 2 4 5 3 diastereotopic Problem 8.33B CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.55.0 ppm 2030405060708090100110120130 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 % T ra ns m it ta nc e 833 1057 1381 1450 2924 3332 160150140130120110100908070605040 50 100 41 55 69 81 95 109 123 138 156 2526 ppm 13 / P 150.9 MHz CH3HO CH3 CH3 Citronellol C10H20O Mol. Wt.: 156 101 2 3 4 5 6 7 9 8 1 7 6 2 4 5 3 8 9 10 1 6 2 4 5 3 8 9 10 OH Problem 8.34A CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.55.05.5ppm ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 ppm 1.01.52.02.53.03.54.04.55.05.5 ppm 20 40 60 80 100 120 20 40 60 80 100 120 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.01.52.0 ppm 20 30 40 CH3HO CH3 CH3 Citronellol C10H20O Mol. Wt.: 156 101 2 3 4 5 6 7 9 8 1 6 2 4 5 3 8 9 10 OH 1 7 6 2 4 5 3 8 9 10 Problem 8.34B CHAPTER 8 ASSIGNED PROBLEMS Hz 220 200 180 160 140 120 100 80 60 40 20 ppm -20000 -15000 -10000 -5000 10000 5000 0 -20000 -15000 -10000 -5000 10000 5000 0 Hz 65 60 55 50 45 40 35 30 25 20 15 10 5 ppm -17000 -18000 -19000 -20000 -21000 -22000 -23000 -24000 -25000 -17000 -18000 -19000 -20000 -21000 -22000 -23000 -24000 -25000 F1 F2 F2 F1 INADAQUATE 150.9 MHz INADEQUATE 150.9 MHz O CH3H3C CH3 Camphor C10H16O Mol. Wt.: 152 1 2 3 45 6 7 9 8 10 1 2 3 1 7 6 4 5 3 8 9 10 Problem 8.35C CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.5 ppm 2030405060708090100110120130140150160170 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 2350 Hz 1000 Hz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 1041 1242 1373 1466 1743 2877 2962 130120110100908070605040 50 100 x 3043 55 70 115 130 2300 Hz 700 Hz850 Hz 550 Hz 13 / P 150.9 MHz In the above insets each tick mark is 10 Hz H3C O CH3 O CH3 2-Methylbuty acetate C7H14O2 Mol. Wt.: 130 1 2 3 4 5 6 7 1 7 6 2 4 5 3 1 7 is doublet 6 is triplet 5 4 5 3 Problem 8.36A CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.5ppm ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 1.0 1.5 2.0 2.5 3.0 3.5 4.0 ppm 1.01.52.02.53.03.54.04.5 ppm 10 20 30 40 50 60 70 10 20 30 40 50 60 70 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 0.850.900.95 ppm 10 15 H3C O CH3 O CH3 2-Methylbuty acetate C7H14O2 Mol. Wt.: 130 1 2 3 4 5 6 7 1 7 6 5 4 5 3 7 7 6 4 5 3 6 1 Problem 8.36B CHAPTER 8 ASSIGNED PROBLEMS 9 8 7 6 5 4 3 2 1 ppm 30405060708090100110120130140150160170 ppm MASS IR 1H NMR 600 MHz 1280 Hz38603880 Hz 300320 Hz 13C/DEPT NMR 150.9 MHz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3201 2962 2870 1612 1550 1473 1412 1265 949 764 663 16015014013012011010090807060 50 100 16 4 14 9 13 6 12 1 10 3 917 7 65 39203940 Hz 3720 Hz 171.0171.5 ppm O OH H3C CH3 β-Thujaplicin C10H12O2 Mol. Wt.: 164 1 2 3 4 5 6 7 10 9 8 7 6 5 3 8 9 10 OH 1 7 6 2 4 5 3 8 9 10 Problem 8.38A CHAPTER 8 ASSIGNED PROBLEMS 7 6 5 4 3 2 1ppm ppm 7 6 5 4 3 2 1 7 6 5 4 3 2 1 ppm 7 6 5 4 3 2 1 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 6.26.46.66.8ppm ppm 6.2 6.4 6.6 ppm 6.26.46.66.8 ppm 125 130 135 140 O OH H3C CH3 β-Thujaplicin C10H12O2 Mol. Wt.: 164 1 2 3 4 5 6 7 10 9 8 7 6 5 3 8 9 10 7 6 5 3 8 9 10 7 6 5 3 Problem 8.38B CHAPTER 8 ASSIGNED PROBLEMS Hz 20406080100120140160 ppm -20000 -15000 -10000 -5000 20000 15000 10000 5000 0 -20000 -15000 -10000 -5000 20000 15000 10000 5000 0 Hz 115120125130135140145150155160165170175 ppm 20000 15000 10000 5000 0 20000 15000 10000 5000 0 F1 F1 F2 F2 INADEQUATE 600 MHz INADEQU T 150.9 MHz O OH H3C CH3 β-Thujaplicin C10H12O2 Mol. Wt.: 164 1 2 3 4 5 6 7 10 9 8 4 8 9 10 1 7 6 2 4 5 3 Problem 8.38C CHAPTER 8 ASSIGNED PROBLEMS Hz 200 180 160 140 120 100 80 60 40 20 ppm -20000 -15000 -10000 -5000 5000 0 -20000 -15000 -10000 -5000 5000 0 Hz 60 55 50 45 40 35 30 25 20 15 10 5 ppm -17000 -18000 -19000 -20000 -21000 -22000 -23000 -24000 -25000 -17000 -18000 -19000 -20000 -21000 -22000 -23000 -24000 -25000 F1 F2 F2 INADEQUATE 600 MHz F1 INADEQUATE 150.9 MHz H3C CH3 CH3 O Br 3-Bromocamphor C10H15BrO Mol. Wt.: 230 1 2 345 6 7 89 10 1 2 3 1 7 6 4 5 3 10 Problem 8.39C CHAPTER 8 ASSIGNED PROBLEMS 1.01.11.21.31.41.51.61.71.81.92.02.1 ppm 2530354045505560657075 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 1501401301201101009080706050 50 100 55 71 81 93 108 111 136 139 154 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 841 987 1080 1219 1373 1466 2970 13 / 15 .9 MHz FM (found) = 154.1351 O CH3 CH3 CH3 Cineole C10H18O Mol. Wt.: 154 1 23 4 5 6 7 8 9 10 2 4,6 3,7 8,9 8,9 10 1 7 3,7 2 4,6 5 3, 4,6 10 Problem 8.40A CHAPTER 8 ASSIGNED PROBLEMS 1.01.21.41.61.82.02.2ppm ppm 1.0 1.2 1.4 1.6 1.8 2.0 1.0 1.2 1.4 1.6 1.8 2.0 ppm 1.01.21.41.61.82.02.2 ppm 22 24 26 28 30 32 34 22 24 26 28 30 32 34 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz O CH3 CH3 CH3 Cineole C10H18O Mol. Wt.: 154 1 2 3 4 5 6 7 8 9 10 1 7 6 2 4 5 3, 8,9 10 7 4,6 2 4,6 3, 8,9 10 3,7 4,6 Problem 8.40B CHAPTER 8 ASSIGNED PROBLEMS 3.03.54.04.55.05.56.06.57.0 ppm 405060708090100110120130140 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz 43504400 Hz 27002750 Hz 19502000 Hz % o f B as e Pe ak m/z 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3402 2939 2831 1720 1466 1350 1088 972 748 1601501401301201101009080706050 50 100 164 146 131 121 104 9177 65 16001650 Hz 13 / P 150.9 MHz OH OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164 1 34 5 6 7 8 9 10 2 1 7 6 2 4 5 3 8 9 10 1 7 6 2 5 3 8 10 OH 3 Problem 8.42A CHAPTER 8 ASSIGNED PROBLEMS 3.03.54.04.55.05.56.06.57.07.5ppm ppm 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm 3.03.54.04.55.05.56.06.57.07.5 ppm 40 60 80 100 120 40 60 80 100 120 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 7.27.37.4 ppm 126 128 130 OH OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164 1 34 5 6 7 8 9 10 2 1 7 6 3 5 3 8 10 OH 1 7 6 2 5 3 8 10 2 Problem 8.42B CHAPTER 8 ASSIGNED PROBLEMS 3.03.54.04.5 ppm ppm 40 50 60 70 80 90 F2 F1 HMBC 600 MHz 7.17.27.37.47.5 ppm ppm 40 50 60 70 80 90 ppm 7.17.27.37.47.5 ppm 125 130 135 140 145 ppm 3.03.54.04.5 ppm 125 130 135 140 145 OH OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164 1 34 5 6 7 8 9 10 2 1 7 6 2 4 5 3 8 9 10 1 7 6 2 5 3 8 10 OH F1 3 Problem 8.42C CHAPTER 8 ASSIGNED PROBLEMS ppm 1.52.02.53.03.54.04.55.0 ppm 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 F2 F1 HMBC 600 MHz H3C HO C O O C11H20O3 Mol. Wt.: 200 1 2 3 4 5 6 7 8 9 10 Ethyl 3-hydroxy-3,6- dimethylhept-6-enoate 11 1 7 6 2 4 5 8 9 11 10 7 2 4 5 3 8 9 11 10 OH F1 Problem 8.43C CHAPTER 8 ASSIGNED PROBLEMS 6.87.07.27.47.67.88.0 ppm 406080100120140160180200 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 600 MHz % o f B as e Pe ak m/z 15010050 50 100 178149 136 121 9365 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3325 2962 1658 1597 1281 1211 1173 841 1.52.02.53.0 ppm 13 / 15 .9 MHz O OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178 1 2 3 4 5 6 7 8 9 7 6 2 3 8 9 OH 1 7 6 2 4 5 3 8 9 Problem 8.44A CHAPTER 8 ASSIGNED PROBLEMS 12345678ppm ppm 1 2 3 4 5 6 7 8 1 2 3 4 5 6 7 8 ppm 12345678 ppm 20 40 60 80 100 120 20 40 60 80 100 120 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz O OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178 1 2 3 4 5 6 7 8 9 7 6 2 3 8 9 7 6 2 3 8 9 OH Problem 8.44B CHAPTER 8 ASSIGNED PROBLEMS 1.52.02.53.03.54.04.55.0ppm ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 ppm 1.52.02.53.03.54.04.55.0 ppm 20 40 60 80 100 120 140 160 180 20 40 60 80 100 120 140 160 180 F2 F2 F1 F1 HMQC 600 MHz COSY 600 MHz ppm 1.52.02.53.0 ppm 20 30 40 50 H CH3 H2C O HO C10H16O2 Mol. Wt.: 168 1 2 3 4 567 8 9 10 2-((1R,2S)-1-methyl-2-(prop-1-en-2- yl)cyclobutyl)acetic acid 1 7 4 5 3 9 10 1 7 4 5,4 3 9 10 7 5 10 1 Problem 8.45B CHAPTER 8 ASSIGNED PROBLEMS F2 1.21.41.61.82.02.22.42.6 ppm4.85.0ppm ppm 20 25 30 35 40 45 50 1.21.41.61.82.02.22.42.6 ppm ppm 4.85.0 ppm 150 F1 HMBC 600 MHz H CH3 H2C O HO C10H16O2 Mol. Wt.: 168 1 2 3 4 567 8 9 10 2-((1R,2S)-1-methyl-2-(prop-1-en-2- yl)cyclobutyl)acetic acid 1 7 5,4 3 8 9 10 1 7 6 2 4 5 3 9 10 7 4 5 Problem 8.45C CHAPTER 8 ASSIGNED PROBLEMS 1.01.52.02.53.03.54.04.55.0 ppm 30405060708090100110120130140 ppm MASS IR 1H NMR 600 MHz 13C/DEPT NMR 150.9 MHz 21602180 Hz 122012401260128013001320134013601380140014201440 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 787 1049 1365 1466 2916 3332 1601501401301201101009080706050 50 100 53 65 77 91 105 122 133 148 151 166 CH2CH2OH Nopol C11H18O Mol. Wt.: 166 11 1 2 3 4 5 6 78 9 10 1 7 4 5 3 8 9 11 10 1 7 6 2 4 5 3 8 9 11 10 OH 4 9 Problem 8.46A CHAPTER 8 ASSIGNED PROBLEMS 2.53.03.54.04.55.05.56.06.57.07.58.0 ppm MASS IR 1H NMR 600 MHz 4500460047004800 Hz O O OC HOH2C O % o f B as e Pe ak m/z 300 50 100 317305 277 25020015010050 50 100 154 136 105 77 4000 3000 2000 1000 Wavenumber (cm-1) 50 100 % T ra ns m itt an ce 3456 2939 2877 1751 1712 1281 1072 717 CI Reagent gas methane m/z 3000310032003300 Hz 130014001500 Hz 22002250 Hz 17001750 Hz OH FM (found) = 277.1083 by CI O O O C CH2OH O 5-(Benzoyloxy)hexahydro-4- (hydroxymethyl) C15H16O5 Mol. Wt.: 276 12 13 1 2 34 5 6 7 8 9 10 11 7 6 2 4 10 3 8 12 9 11 12 10 Problem 8.47A CHAPTER 8 ASSIGNED PROBLEMS 2.53.03.54.04.55.05.56.06.57.07.58.08.5ppm ppm 3 4 5 6 7 8 3 4 5 6 7 8 ppm 2.53.03.54.04.55.05.5 ppm 2.5 3.0 3.5 4.0 4.5 5.0 5.5 2.5 3.0 3.5 4.0 4.5 5.0 5.5 F1 F1 F2 COSY 600 MHZ COSY 600 MHZ O O OC HOH2C O O O O C CH2OH O 5-(Benzoyloxy)hexahydro-4- (hydroxymethyl) C15H16O5 Mol. Wt.: 276 12 13 1 2 34 5 6 7 8 9 10 11 7 6 2 8 9 11 12 10 7 6 4 3 9 11 12 10 Problem 8.47B CHAPTER 8 ASSIGNED PROBLEMS ppm 2.53.03.54.04.55.05.56.06.57.07.58.0 ppm 40 50 60 70 80 90 100 110 120 130 F2 HMQC 600 MHz 405060708090100110120130140150160170180 ppm F1 13C/DEPT NMR 150.9 MHz 77.077.5 ppm O O OC HOH2C O ppm 2.42.52.62.72.82.93.0 ppm 35 40 129130 ppm O O O C CH2OH O 5-(Benzoyloxy)hexahydro-4- (hydroxymethyl) C15H16O5 Mol. Wt.: 276 12 13 1 2 34 5 6 7 8 9 10 11 1 7 6 2 4 5 3 8 13 9 11 12 10 12 7 6 2 4 7 3 8 13 9 11 12 10 OH 8 10 10 2 4 12 3 8 13 9 11 12 10 6 Problem 8.47C CHAPTER 8 ASSIGNED PROBLEMS