Chem 353-2

5 75 70 65 60 55 50 45 40 35 30 ppm caffeine 13 12 11

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Unformatted text preview: 9 8 7 6 5 ppm (ppm) 6.5 7.5 8.5 9.5 10.5 11.5 210 200 190 180 170 160 150 140 130 120 (ppm) Use to argue attachment site postion. 192.4* 136.4 134.5* 129.7* 129.0* * odd number of hydrogens 220 200 180 160 140 120 100 80 60 40 20 0 ppm Cannizaro Reaction D2O exchange 6.0 5.5 5.0 4.5 4.0 ppm 3.5 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 220 200 180 160 140 120 100 80 60 40 20 0 ppm Cannizaro Reaction D2O exchange 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 220 200 180 160 140 120 100 80 60 40 20 0 ppm Diels-Alder Reaction 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm (ppm) 3 4 5 6 7 8 150 130 110 90 (ppm) 70 50 30 220 200 180 160 140 120 100 80 60 40 20 0 ppm Diels-Alder Reaction 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 220 200 180 160 140 120 100 80 60 40 20 0 ppm Hydroboration Oxidation 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm * Use this reference molecule to argue proper peak assignments. Actual Positions 77.642 77.230 76.803 62.946 32.868 31.982 29.587 29.449 25.924 22.796 14.219 80 70 60 50 40 30 20 ppm Hydroboration Oxidation 2501.09 2484.24 2467.04 2456.78 Calculate both cis and trans coupling constants. Jcis = Jtrans = 5.0 4.9 ppm 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm Actual Positions 139.447 114.297 77.482 77.230 76.978 34.084 32.001 29.179 29.087 22.877 14.303 140 130 120 110 Plotname: --Not assigned-- 100 90 80 70 60 50 40 30 20 10 ppm Freidel Crafts Acetylation 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 220 200 180 160 140 120 100 80 60 40 20 0 ppm Freidel Crafts Acetylation 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm (ppm) 4.2 4.4 4.6 4.8 5.0 5.2 5.4 5.6 5.8 6.0 82 80 78 76 74 72 (ppm) 70 68 66 78 76 74 ppm 72 70 220 200 180 160 140 120 100 80 60 40 20 0 ppm Freidel Crafts Acetylation 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm (ppm) 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 90 80 70 60 50 (ppm) 40 30 220 200 180 160 140 120 100 80 60 40 20 0 ppm Grignard Reaction 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 ppm 220 200 180 160 140 120 100 80 60 40 20 0 ppm Grignard Reaction 8.0 7.5 7.0 6.5 (ppm) 6.5 7.0 7.5 8.0 8.5 9.0 6.0 5.5 5.0 ppm 138 136 134 132 130 128 126 124 122 120 (ppm) 220 2...
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This note was uploaded on 04/06/2011 for the course CHEM 353 taught by Professor Bronson during the Winter '11 term at BYU.

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