HW 18: Solving structures using IR and MS (85 pts) Due: Wed 1/25/21 Name 1. (34 pts) This pleasant smelling liquid has the following elemental analysis: 68.2% carbon, 13.6 % hydrogen, 18.2% oxygen. Mixing this compound with the chromic acid reagent, an orange liquid is obtained, whereas the Lucas Test shows the immediate formation of two phases. Using this information and the spectral data below, determine the identity of the compound. Start by determining the molecular formula from the elemental analysis and then calculate the # of elements of unsaturation. In your analysis, i) interpret the results of the qualitative tests, il) assign all the relevant peaks in the IR spectrum and mi) provide a fragmentation analysis for the peaks listed for the mass spectrum abundance 73 100 70 59 59 74 55 81 41 22 29 17 15 8 2. (34 pts) This pleasant smelling liquid has the following elemental analysis: 69.8% carbon, 11.6 % hydrogen, 18.6% oxygen. Upon mixing this compound with the chromic acid reagent, a dark green solution is obtained. Reduction of the unknown compound with LIAIH, produces an achiral alcohol; this alcohol produces a greenish liquid when mixed with chromic acid and remains for hours as a single phase when mixed with the Lucas Reagent. Use this information (show) and the spectral data below to determine the identity of the compound. Start by determining the molecular formula from the elemental analysis and then calculate the # of elements of unsaturation. In your analysis, I) interpret the results of the qualitative tests, ii) assign all the relevant peaks in the IR spectrum and i) provide a fragmentation analysis for the peaks listed for the mass spectrum. Keep in mind that there may be more than one fragment for a given m/z value. m/ Wabundance 86 27 71 40 meet 57 100 43 61 29 S2 15 9 1720 H