1. Give the structural formula for the unknown compound.
2. Explain the IR, 1H NMR and MS (EI) spectra based on the structure given in I.
3. Provide mechanistic explanations for fragmentations in the MS spectrum.
4. Suggest and describe a less destructive MS technique and sketch the corresponding MS spectrum. Explain differences between the given MS spectrum below with the predicted spectrum.

IR Spectrum of the Unknown Organic Compound 'H NMR Spectrum of the Unknown Organic Compound 4000 3000 2000 1500 1000 500 97 65 100 T MS Spectrum (El) of the Unknown Organic Compound 67 I 3 T 2 8 7 6 5 4 1 0 175 173 13C NMR Spectrum of the Unknown Organic Compound Note that this spectrum is provided to assist you in answering Question 1 - no detailed analysis is required 147 145 149 147 1908 triproporto 20 truny 200 220 40 60 80 100 140 160 180 120 m/z T 50 200 150 100 0