Problem Set 2

The compound whose proton decoupled carbon-13 spectrum is shown below contains carbon, hydrogen, oxygen, and bromine. The spectrum is referenced to CDCl3, which appears as an equally intense triplet at 77 ppm.

  1. Determine whether the fuctional group is:
    • an alcohol
    • an ether
    • a ketone
    • an aldehyde
    • an ester
    • a carboxylic acid
  2. How many chemically different carbons are present?
  3. Are there both aromatic and aliphatic groups or just one type?
  4. Is the peak at 25 ppm due to a carbon that is likely to be attached to an oxygen?

The proton spectrum of the same compound is given below.

  1. Can you now assign the peak in the carbon spectrum at 25 ppm?
  2. Is the compound a mono-substituted aromatic or a di-substituted aromatic?
  3. Is the bromine likely to be attached to the benzene ring?
  4. Give two alternatives for the structure of the compound.