8.

Infrared Spectroscopy
Infrared (IR) Spectroscopy is an analytical method that measures the
absorbance of a select band of electromagnetic radiation within a sample. The
wavelength of radiation that is absorbed is characteristic of different types of
chemical bonds within the sample. A graphical representation of the absorption
of the electromagnetic radiation by the sample makes an IR spectrum.
Organic chemists use infrared spectroscopy as a means of identifying
various types of bonds within in a molecule. This can aid in determining the
functional groups present or absent. IR is often used in combination with other
techniques, especially nuclear magnetic resonance (NMR) spectroscopy.
In this class you will learn how to operate a Nicolet Fourier transform
infrared (FT-IR) spectrometer and obtain an IR spectrum from your sample.
You will learn how to interpret IR spectra and determine the chemical bonds
present. You will then use this information to identify the functional groups
present and select the identification of the material from a list of possible
materials.

PRE-EXPERIMENT ASSIGNMENT

Study this chapter of the manual, the lecture notes on the Chemistry
Department web site, the “IR Spectra Interpretation” document posted on the
web site and the appropriate section in your lecture textbook.
You do not need to write a notebook pre-lab for this experiment. Instead
you will be given an in-class assignment to do for these points.
A major part of this lab will be in operating an Infrared Spectrometer.
Your instructor will explain and show you how to do this. Since all the steps
involve operation of equipment, a pre-lab notebook procedure does not need to
be written. It will however be very important for you to write down in your
notebook all of the possible unknown compounds from the on-line notes. If you
do not have this information, it will be very difficult for you to successfully
determine the identity of your unknown material and points may be lost.

A student who has prepared for the Infrared Spectroscopy experiment

should be able to:

1. Identify the relative energy, frequency, and wavelength of infrared light

compared with other types (including gamma rays, x rays, ultraviolet and
visible light, microwaves, and radio waves). Also, identify the change that
occurs in molecules when infrared light is absorbed.
2. Explain the relationship between frequency, energy, wavelength and
wavenumbers.
3. Define the major absorbance regions in the IR. Know the frequency which
each major chemical bond absorbs in the IR.
4. Know the bonds which make up each functional group.
5. Define, identify, recognize, and explain the use of each of the following:
IR (infrared) spectroscopy, neat samples, salt plates (including how to clean
them), Nujol mull, and KBr pellet.
6. Identify and explain safety considerations for this experiment.
7. Perform the day's experiment safely and successfully.

Quizzes given after the experiment has been performed may also include:

8. If given a chemical bond or functional group, choose in which of the 5

regions it will absorb.
9. If given an IR spectrum, be able to determine the chemical bonds present.
10. Give or recognize a probable absorption frequency in cm-1 in the IR
spectrum of a compound containing any of the following functional groups;
Amines, Alcohols, Alkynes, Terminal Alkynes, Nitriles, Alkanes, Alkenes,
Aldehydes, Carboxylic Acids, Esters, Amides, Aldehydes, Ketones, and Ethers.
(Detailed instructions of spectrum interpretation can be found in “Sample IR
Spectra” located on the organic web site.
11. Draw a reasonable IR spectrum if given a compound name or structure.

Safety Precautions

All of the compounds you will take IR spectra of in this experiment are at
least slightly toxic and flammable. Wash your hands after conducting the
experiment.
Infrared radiation is relatively (but not completely) harmless. The safety
instructions on the IR spectrometer say “Do not stare into beam,” because long
exposures to IR radiation can be damaging.

EXPERIMENT

Preparing the sample

Handle salt plates with care. The salt plates are very sensitive to
moisture and will break easily. Each pair costs approximately $25. If you are
the first student, remove the jar containing the salt plates from the desiccator.
(A desiccator is a low humidity vessel.) Remove two salt plates from cotton
envelope. Place the two salt plates on a Kim-Wipe. Clean plates by placing a
few drops of acetone on each salt plate, then wiping clean with Kim-Wipe.
Throw Kim-Wipe away. Place 1-2 drops of unknown liquid on one salt plate.
Cover with other salt plate. Carefully place in sample holder. Take sample to IR
to obtain spectrum.
Obtaining the IR spectrum

Take sample to IR spectrometer. Follow instructions posted adjacent to

machine.

Cleaning the salt plates

Remove salt plates from sample holder. Place salt plates on Kim-Wipe.
Place a few drops of acetone on each salt plate. Using a new Kim-Wipe, rub
each salt plate with the acetone. If another student is waiting to run the
spectrometer, help them go through the process. If you are the last user,
replace each salt plate in a separate cotton envelope. Place each envelope
within the plastic jar. Place the plastic container back in the desiccator.
Throw away any used Kim-Wipes.

Cap your unknown sample. Replace unknown sample in its designated spot
within the unknown sample container.

POST-EXPERIMENT ASSIGNMENT

Complete the datasheet and turn in before leaving class. Ensure your IR
spectrum is stapled to the datasheet. Turn in the white notebook pages from
your lab notebook. Staple multiple sheets together. Tear off rough edges.
Prepare for the IR portion of the next quiz. Remember that you may be
asked questions on anything you should have learned from assigned readings,
pre-experiment lecture, or doing the experiment.

Revised December 17, 2017 S. L. Weaver

BOND IR ABSORBANCE REGIONS

Bonds Position (cm-1) strength and Shape

O-H/ NH 3200-3600
(Hydrogen bonded to Nitrogen & Oxygen)
-O-H 3200-3600 rounded
-N-H, -NH2 3200-3600 single or double pointed
-COOH 2500-3600 very broad

C-H 2800-3100, 3300

(Hydrogen bonded to Carbon)
sp ≡C-H 3300 narrow and very pointed
sp2 =C-H 3000-3100 shoulder to left of sp3 C-H
sp3 C-H 2800-3000 multi-peaked

≡ 2100-2300
(Triple Bond; Carbon to carbon and carbon to nitrogen)
C≡N 2100-2300 sharp
C≡C-H 2100-2300 sharp

= 1600-1800
(Double Bond; Carbon to )
C=O 1650-1800 strong slightly rounded
C=C 1600-1680 medium , sharp

Carbon to oxygen single bond 1000-1300 limited value

-C-O- 1000-1300 use only when necessary