Looking at infrared spectra:

You have been given the IR spectra of 4 molecules along with their molecular formula.
Remember that unclear peaks in the 1000-1400 cm-1 region on the spectrum is called the
fingerprint region, showing that there many C-C and C-H bonds in the molecule.
Task 1: For each sample given, to circle and label the peaks and say which functional group
is responsible for this absorption.
This will be given to you at the end of your unit 2 paper:

Example:
Spectrum A:

Spectrum B:
Spectrum C:

Spectrum D: C3H7Br

TASK 2: Identify and name the molecules giving each of the spectra shown above:
Task 3: For the following compounds, write their skeletal formula and then describe what
you would expect to see on their IR spectrum. An example of a description is given to you
below:
Ethanoic acid: I would expect to see several absorptions peaks.
A large absorption peak in the 2300-3550cm-1 region due to the O-H bond of the carboxylic
acid. This peak would be very broad. Another peak would be observed in the 1650-1750cm-
1
region due to the C=O bond in the carboxylic acid group. There also is a C-O bond in the
group, so I expect to see an absorption peak around 1000-1300cm-1. Finally, the C-H bonds
should show an absorption peak at 2800-3100cm-1 but could be shadowed by the very large
peak observed due to the carboxylic acid O-H bond.
Write a similar description for the following molecules:
1. Butanone (use the spectrum you have as a help for your first one)
2. Propanoic acid
3. Chloroethane
4. Propene
Task 4:
Use your knowledge of the mass spectrometer and infra-red spectroscopy to solve the
following problems. (The Ar used here remain simple, C=12, H=1 etc…)
1. A molecule of formula C5H10O2 shows a very broad absorption peak of wavelength
2300-3550cm-1. It also shows a strong absorption at 1700cm-1. Draw the full
displayed formula and name this compound.
2. A molecule of molecular mass 60g.mol-1 has been analysed using infra-red
spectroscopy. The spectrum shows a strong absorption peak at 3350 cm-1 and
another one (sharp) at 1200cm-1, as well as sharps peaks between 2800 and 3100cm-
1
. Use this information to find the molecular formula of this compound and name the
homologous series to which it belongs.
3. An unknown molecule is vaporised and analysed using a mass spectrometer. Two
peaks in the ratio 3:1 are observed at m/z= 78 and m/z=80. The spectrum also shows
clear peaks at m/z=63 and m/z=65. There is no peak observed at m/z= 29.
It also has been analysed using infra-red spectroscopy. The spectrum shows sharp
peaks between 2800 and 3100cm-1. A sharp peak is also observed at 700cm-1. Use
this information to find out the structure of the compound, you should include the
fully displayed formula of this compound and its name. Help: use the IR data first to
get you on the right track!
4. Propane nitrile has the formula C3H5N. The molecule shows a sharp absorption peak
at 2200cm-1 and some absorption between 2800 and 3100cm-1. Use this information
to draw the displayed formula of propane nitrile.