A compound has molecular formula C5H8O, and exhibits the IR and 1H NMR spectra shown. What is it?




Questions to ask:
  1. How many degrees of unsaturation?
  2. Given DoU and the atoms present, what functional groups do we see in the IR?
  3. Do the functional groups necessarily have any hydrogens? Can we identify those in the 1H NMR spectrum?
  4. How many different CHn groups are there?
  5. How many hydrogens are there at each unique position? (Look at integrals)
  6. What is the coupling among hydrogens? (How many hydrogens are nearby?) Be sure to expand the spectrum and look closely, especially to identify different coupling constants.

Go to this page to test your proposed structure (note: OH protons and long-range coupling are not predicted), or look it up in the Spectral Database.
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Last updated: 01/17/2014