CH301 Semester 1 2019

Tutorial Solutions on Infrared Spectroscopy

1. State whether the following pairs of compounds could be distinguished using their IR spectra.
Give reasons

a). PhCH2NH2 and PhCONH2

PhCH2NH2 molecule, has a primary amine (-NH2) which

will give two sharps peaks around 3000cm-1.

PhCONH2 has a carbonyl (C=O) which will have a stretch around 1640-1680 cm-1

b). p-H2N-C6H4-COOMe and p-Me-C6H4-COOMe

p-H2N-C6H4-COOMe has a para-primary amine (p-H2N), will give two sharps peaks
around 3000cm-1.

c). Cyclohexanone and 3-methylpentanol

3-methylpentanol has an –OH group, which will give a broad rounded tip peak around 3300cm-1
and cyclohexanone will show a peak at 1700 cm-1 for the C=O

d). Hexanol and phenol

Both compounds has –OH groups, however, phenol

will give aromatic C=C bond stretches around
1600cm-1

e). pentanoic acid and 2-pentanone

Both the compounds have C=O bond giving peak at 1710cm-1, while pentanoic acid has –OH group
which will have a broad peak at 2500-3500cm-1.
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.

benzyl alcohol

C-H Stretch

O-H stretch
(broad)
 C=C 1-octene
C-H
C-H Stretch

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.

carboxylic acid acylchloride

O-H
C=O stretch

C=O stretch

aldehyde amide

C=O N-H Bending

C=O Stretch
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.
 1600cm-1 - C=O stretch
 1710cm-1 - C=O stretch
 2400-3400cm-1 - C-H stretch (sp3 alkane)

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.

0-H

Structure of compound: Butanol

b. Boiling point of 155°C and molecular formula of C6H10O.

C-H stretch

C=O

Structure of compound: Cyclohexanone