Question

An unlabeled bottle of a chemical is found in an abandoned chemistry laboratory. Shown on the following page are the IR, 1H and 13C NMR and MS Spectra collected for the compound. Use the data provided below and reasoned arguments to deduce the structure of the unknown sample that has been found and the name of the compound. NMR and IR tables are supplied below. Please note that while you will need to refer to chemical shifts in your reasoned argument, exact calculation/prediction of peak shift is not required. Having said that, provide a detailed explanation on how you have arrived to your answer.

Bonds to H Figure 1: Main regions in an IR spectrum Triple Double Single Bonds Bonds Bonds C=C C-C c=c|| C=N C-N |CEN C=0 C-0 X-H 4000 2700 2300 2100 1850 1600 400 Wavenumber (cm') Figure 2: Typical 'H and "C chemical shift ranges of some functional groups 'H NMR | H —C— C-H —C—H -C-CH vinylic C=C–C– Z = 0, N, halogen saturated -ċ-OH allylic 129. 08. 06.5 12 9.0 8.0 6.5 2.5 1.5 4.5 d (ppm) 13C NMR C-N C–CI C– C=C C=0 C=C spº carbon C–0 200 150 50 100 8 (ppm)