CH301 Semester 1 2017
Tutorial on Infrared Spectroscopy
1. State whether the following pairs of compounds could be distinguished using their IR
spectra. Give reasons
a). PhCH2NH2 and PhCONH2
b). p-H2N-C6H4-COOMe and p-Me-C6H4-COOMe
c). Cyclohexanone and 3-methylpentanol
d). Hexanol and phenol
e). pentanoic acid and 2-pentanone
2. List 3 factors that affect the frequencies in IR spectroscopy.
3. Below is the IR spectrum of 2-phenylethanol. Identify all the distinct absorptions.
4. The following are the spectra of benzyl alcohol and 1-octene recorded in chloroform.
Identify each spectrum to the two compounds and assign the major absorptions.
5. The four spectra shown below are of an aldehyde, a carboxylic acid, acylchloride and an
amide. Use the IR spectra to identify each of the following compounds.
6. The liquid film IR spectrum of 2,4-pentandione (acetylacetone) shows absorption bands
at 1600cm-1 (strong and broad); 1710cm-1 (less stronger than 1600cm-1 band but
sharper); a very broad band stretching from `2400-3400cm -1, which remains unchanged
on dilution. Identify the functional groups responsible for these absorption bands.
7. Below is an IR spectrum of a two liquid compounds containing C, H and O. Identify all
relevant information and determine the structure of the compound.
a. Molecular weight of 74.
b. Boiling point of 155°C and molecular formula of C6H10O.