5. (20 points) Use the 'H, C, and DEPT NMR spectra on the following pages to determine the structure of a compound with formula C12H160. Draw the structure of the molecule, along with the number and/or letter code for signal assignments, in the box below and on the following page. On each of the spectra, show your work in interpreting the signals. Clearly label each signal in both spectra with an assignment corresponding to the structure. 30 220 2io 200 190 180 170 160 150 140 130 110 90 BO 50 120 100 DEPT 135 ppm 40 30 20 10 50 220 219 220 150 150 i20 i20 150 140 130 120 110 100 DEPT 45 ppm 90 80 220 210 200 190 180 170 160 150 140 130 90 BO 70 80 50 40 120 110 100 13C (ppm) 30 20 10 0 3548.46 -3540.22 3531.98 342624 3423.95 3-421.88 -3418.00 3415.71 336627 -3361.92 3358.03 3355.74 3353.68 3413.65 at 98 -3287.08 -3285.02 3.282.73 318293 317310 3167.60 3157.76 2913.77 -2911.05 2898.44 -2895.69 2811.23 -2808.49 -2801.39 2798.64 7.1 7.0 6.9 ... 6.7 1H (ppm) 6.5 6.4 5.90 5.65 5.60 5.75 5.70 5.6 5.60 5.65 5.50 1H (ppm) () 1233.56 1226.51 946.08 939.02 932.11 925.07 -918.12 911.10 -904.00 897.09 458.45 451.46 6.00 2.00 1.00 00 100 1.00 2524 20 1.0 0.9 I I 2.0 11.5 110 10.5 10.0 8.5 2.0 7.5 5.0 4.5 4.0 DE 2.5 2.0 1.0 7.0 8.5 6.0 5.5 1H (ppm) 0.500 81