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.
- Determine whether the fuctional group is:
- an alcohol
- an ether
- a ketone
- an aldehyde
- an ester
- a carboxylic acid
- How many chemically different carbons are present?
- Are there both aromatic and aliphatic groups or just one type?
- 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.
- Can you now assign the peak in the carbon spectrum at 25 ppm?
- Is the compound a mono-substituted aromatic or a di-substituted aromatic?
- Is the bromine likely to be attached to the benzene ring?
- Give two alternatives for the structure of the compound.