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, ii) assign all the relevant peaks in the IR spectrum and iii) provide a fragmentation analysis for the peaks listed for the mass spectrum. m/z % abundance 80 73 100 70 59 6a 59 74 55 81 41 22 & 29 17 377 15 8 Lace 2008 150 350 Capillary fils between salt plates 1eee Copyright 1992 AVENUMBERS 600.6 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 LiAlH4 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 iii) 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/z % abundance 86 27 71 40 Iflello 57 100 43 61 29 52 15 9 0 1502 Polep WEN. EERS 3H