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.
- Determine whether the fuctional group is:
- an alcohol
- an ether
- a ketone
- an aldehyde
- an ester
- a carboxylic acid
- 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?
- 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.
- What is the carbon that gives rise to the peak at about 63 ppm attached to?
- How many chemically equivalent carbons are there in the benzene ring?
- What is the structure of the compound?