Problem Set 13

This compound contains carbon, hydrogen, and oxygen.

  1. It may be useful to take a first look at the proton spectrum to see if you can determine generally what type of groups are present.

  2. The proton-decoupled carbon-13 spectrum contains six peaks in the "aromatic" region. It is not obvious, but two of these peaks are not due to carbons in the benzene ring.To what kind of carbon can they be attributed?

  3. Now go back to the proton spectrum and look carefully at the region between 6 and 6.6 ppm. Examine particularly the four largest peaks and ignore the other peaks in the 6.2 region. What do these four peaks suggest?
  4. The peak at 4.6 ppm is a doublet. Combine this with the information that you just uncovered about the peaks between 6 and 7 ppm and suggest a structural unit.
  5. Now combine the "main" functional group with the unit above and the singlet at about 2 ppm and the aromatic region and produce a reasonable structure.