Differentiation of Organic Compounds with the Use of Infrared Spectroscopy

Keanu Cruz, Aya El Oirdighi, Franz Robert Estampador and Katrina Evangelista
College of Science, University of Santo Tomas, Manila, Philippines

ABSTRACT

This experiment highlights on learning the Infrared (IR) spectroscopic methods

to elucidate and characterize the identity of different functional groups present. . The
conventional use and care of an IR spectrophotometer were thoroughly discussed.
There are five standard samples and five unknown samples that were manipulated
using the IR spectrophotometer. IR spectra are obtained on an IR spectrophotometer
using the attenuated total reflection (ATR) sampling technique. Data gathered from the
IR Spectrum were observed and documented for the analysis and characterization of
functional groups present.

INTRODUCTION

Absorption of infrared radiation brings about changes in molecular vibrations

within molecules and 'measurements' of the ways in which bonds vibrate gives rise to
infrared spectroscopy. Atom size, bond length and bond strength vary in molecules and
so the frequency at which a particular bond absorbs infrared radiation will be different
over a range of bonds and modes of vibration.
Spectroscopy is the assimilation and the effusion of light as associated to the
subordination of various processes on the wavelength of a radiation. Electromagnetic
radiation, which comprises light, has properties of particles and waves. It can be
diffused, imbibed, or reflected by matter. Electromagnetic radiation in the infrared (IR)
region of the spectrum has the meticulous energy to cause different bonds in a
molecule to stretch and bend. Discrete functional groups have a characteristic
absorption in the IR region.
Infrared (IR) spectroscopy is a spectroscopic technique used to determine the
absorption amount of different infrared frequencies by a certain specimen of an organic
compound on an IR beam. A persistently changing magnitude of magnetic and electric
fields in directions that are proportional to the direction in which the wave is traveling is
procured by the transverse waves of electromagnetic radiation. Changes in the
magnetic and electric fields are able to cause various changes in molecules. Each
region of the spectrum can be used to scrutinize profuse aspects of the properties and
structure of molecules, depending on the aggregation of energy transmitted to the
molecule.
 The information contained in an IR spectrum originates from molecular
vibrations. These are either fundamental modes that are associated with the vibrations
of specific functional groups, complex modes of the total molecule, vibrational overtones
of summation modes of fundamental vibrations. IR analysis may simply involve the
characterization of a material with respect to the presence or absence of a specific
group frequency associated with one or more fundamental modes of vibration or by a
complex pattern recognition or by a computer search-match algorithm when an
unknown spectrum is compared to an existing reference database

RESULTS AND DISCUSSION

Absorption of infrared radiation brings about changes in molecular vibrations

within molecules and 'measurements' of the ways in which bonds vibrate gives rise to
infrared spectroscopy. Using the IR spectrophotometer, there were 5 known and 5
unknown samples that were manipulated: hexane, isoamyl alcohol, cyclohexanol,
cyclohexanone, and toulene. The chemical structures of different samples forms and
reflects difference in the IR spectrum allowing them for their own identification:

GIVEN STANDARD COMPOUNDS

Figure 1: Infrared spectrum of Hexane

 The sample that was used is hexane. The IR spectrum of hexane (C6H14) in
the functional group region is C–H stretch from 3000–2850 cm-1 also known as
alkanes and mostly can be found exactly 2900 with sharp spike which means strong
and also you will notice that the peak are multiplets. The fingerprint region is located at
1500-700 cm-1. This region originate in interacting vibrational modes resulting in a
complex absorption pattern.

Figure 2: Infrared spectrum of Isoamyl Alcohol

In the isoamyl alcohol IR spectrum, the most prominent bond is due to the O-H
group or a hydroxyl group that appears as a strong, broad band covering the range of
about 3500-3200 cm-1. At 3000-2840 cm-1, a C-H stretch can be found and it is
characterized by a strong peak. This means that there is an alkane in this compound.
The fingerprint region is at 1500-700 cm-1.
 Figure 3: Infrared spectrum of Cyclohexanol
Figure 3 shows a cyclohexanol IR spectrum shows an apparent O-H stretch or a
hydroxyl group characterized as a strong and broad curve found at approximately 3500-
3200 cm-1. This indicates the presence of alcohol. Also, a C-H stretch can be found at
approximately 3000-2840 cm-1, which means that there is an alkane group that is
present. At 1500-700 cm-1, the fingerprint region can be found.
 Figure 4: Infrared spectrum of Cyclohexanone
Figure 4 shows a cyclohexanone IR spectrum, a strong prominent, stake-shaped
bond of highly polar C=O stretch at 1760-1670 cm-1 is found. The strong peak indicates
a presence of a carbonyl group. In addition, a medium C-H stretching at 3000-2840 cm-
1 was read in the spectrum. It shows the presence of an alkane. The fingerprint region
lies at 1500-700 cm-1.
 Figure 5: Infrared spectrum of Toulene
Figure 5 shows an N-H stretch or an amine salt can be found at 3000-2800 cm-1.
In addition to that, there is also an apparent C-H bending at 2000-1650 cm-1
characterized by a weak, pointed peak. This indicates that there is an aromatic
compound in toluene, which makes sense because it is an aromatic hydrocarbon. The
fingerprint region lies at 1500-700 cm-1.
 UNKNOWN SUBSTANCES

Figure 6: Unknown Substance A

Figure 6 shows an IR spectrum that has a N-H stretch at 3000-2800 cm-1 and a
C-H bending at 2000-1650 cm-1, right before the fingerprint region. Thus, we conclude
that the unknown substance is an aromatic hydrocarbon, toulene.

Figure 7: Unknown Substance B

Figure 7 shows an unknown substance with a C=O bond at 1760-1670 cm-1 and C-H
stretch at 3000-2840 cm-1 shown in the IR spectrum. Being able to compare it from the
examined standard samples, we conclude that this is a cyclohexanone.

Figure 8: Unknown Substance C

Figure 8 shows a hexane because of a presence of a C-H stretch or an alkane
group with a peak at 3000-2840 cm-1.

Figure 9: Unknown Substance D

Figure 9 shows a cyclohexanol because of an O-H stretch and a C-H stretch at
approximately 3500-3200 cm-1 and 3000-2840 cm-1.

Figure 10: Unknown Substance E

Figure 10 shows a compound that is almost identical to cyclohexanol in terms of its IR
spectrum. It shows an O-H stretch at 3500-3200 cm-1 and a C-H stretch at 3000-2840
cm-1. These two almost-identical compounts have the same functional groups but can
be distinguished through different absorption patterns with respect to their fingerprint
pattern. Thus, we conclude that this is a cyclohexanol.

EXPERIMENTAL
Before starting the experiment, the students were instructed about the proper
care and usage of the Infrared (IR) spectrophotometer. After providing the class all the
significant information, 1 pump of ethanol was applied to a paper tower that was used to
clean the ATR surface. The IR Spectrophotometer was turned on for calibration. Test
runs are made to ensure that the spectrophotometer is functioning smoothly. After
preparing the equipment, 2-3 drops of the assigned standard (cyclohexanone) and
unknown compound were then dropped using a dropper. The laboratory facilitator
started the reading of the compounds. Results were depicted right after and photos of
the spectra and record were taken. Infrared peaks were observed for analysis.
REFERENCES:

 Gable, K. (2015). Spectroscopic Features of Ketones. Retrieved from

https://www.science.oregonstate.edu/~gablek/CH336/Chapter17/ketonespec.htm
 George, A. (2006). Spectroscopy & structure determination. Retrieved from
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 Smith, B. C. (2017). The Carbonyl Group, Part I: Introduction, 32(9), 31-36. Retrieved
from http://www.spectroscopyonline.com/carbonyl-group-part-i