STRUCTURE DETERMINATION PROBLEMS USING IR AND PROTON NMR SPECTROSCOPY Determine the structure of the six compounds whose IR and PMR spectra are provided on the attached sheets, given the following comments about the provided information and spectra, PMR Spectra The PMR spectrum of each compound is provided, along with peak areas. The peak areas are given as the simplest whole number ratio of protons and are indicated (for example, 4H). Your final structure must be consistent with the chemical shift, peak areas and splitting pattern. Show which protons in the molecule are responsible for each set of peaks. Molecular Formula The molecular formula is given in the upper right-hand corner of each sheet. You don't need the MW or Percent by Weight information. IR Spectra The absorption frequencies printed on the IR spectra are in cm’ona SVL& 0 MF CoH0 d MW 136 re es A ee seme ( wH89 Be tse <<] vipa —— > week BP Wa nice —| tha ia cE ab 3 30 25 abr tei s a 3 & t| MF CioHig oy- MF CioHig ( f\ i BC 89.5 #H 10.5 ——— er ' "ie : 1 r TT 1 7 Por q 2 1 PPM Proton NMASTRUCTURE DETERMINATION PROBLEMS USING IR AND PROTON NMR SPECTROSCOPY - Answers Spectra 1 is 1,6-dichlorohexane LN Spectra 2 is 1-pentene Spectra 3 is 3-phenyl-1-propanol oe ee Spectra 4 is 2-methyl-2-propen-1-ol ? Spectra 5 is butylbenzene Spectra 6 is 2-phenylbutane o~ aX