Problem Set 3

The proton and carbon-13 spectra of a compound containing carbon, hydrogen, oxygen, and bromine is given below. [The carbon-13 is proton-decoupled and is referenced to CDCl3, which appears as an equally intense triplet at 77 ppm.] Notice that expansions of each region in the proton spectrum are also given.

  1. Determine whether the fuctional group is:
    • an alcohol
    • an ether
    • a ketone
    • an aldehyde
    • an ester
    • a carboxylic acid
  2. Examine the peaks in the aliphatic region of the proton spectrum. What two inferences about the structure of the compound can you make from them?
  3. What can you deduce about the structure of the compound from the aromatic region?

Now look at the proton-decoupled carbon-13 spectrum of the same compound.

  1. What is the carbon that gives rise to the peak at about 63 ppm attached to?
  2. How many chemically equivalent carbons are there in the benzene ring?
  3. What is the structure of the compound?