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Question 3 [10 marks]: The elemental analysis for an unknown compound shows: C: 36.7%; H: 6.6%; O: 16.3% (note that the sum of these numbers is less than 100%). The following spectroscopic data (EI-MS, IR, H, 13C NMR) are collected for this compound. (a) Determine the structure of this compound. (b) Explain the bond cleavage mechanism that produces the fragment ion peaks at m/z= 151/153. 100 El-MS 80 - 50 Relative Intensity 40 151 153 M+2(198) M(196) 20 Then 20 40 60 80 100 120 140 160 180 200 m/z LOD my IR TRANSHETTANCEI 31 D 4000 3000 2000 1500 1000 500 HAVENUMBERI- 13C NMR Normal Carbon DEPT-135 DEPT-90 15 32 62 Positive Negative Negative Positive No peak No peak No peak Positive 101 ppm 1H NMR 1 4 2 6 integral 1 T 1 T 1 10 1 9 1 7 | 3 | 2 11 8 00 6 6 5 4 1 0 (1H)/ppm