Jiara Laine Montano

September 29 2016

Ch 26 AA

October 06 2016
Experiment no. 6: Infrared Spectroscopy

Data and results

Qualitative Test
Solubility test

Result
H2SO4 Soluble

Ignition test
Baeyer test
Lucas test
Chromic acid test

Not Sooty
Negative
Negative
Positive

Hydroxamic acid test

Negative

Iodoform test
2,4-DNPH test
Tollens test
Alcoholic AgNO3 test
Iron (III) Chloride test

Positive
Positive
Positive
Negative
Negative

Implications
It can either be an alcohol, alkene, alkyne,
aldehyde, ketone or ester.
Saturated carbon chain.
Not an alkene.
Not a tertiary alcohol.
Either a secondary, primary alcohol or an
aldehyde.
Neither an ester nor a carboxylic acid
derivative.
Might be a methyl ketone.
Either an aldehyde or ketone.
An aldehyde
Not a phenol or enol.
Not a haloalkane.

Table 1. Qualitative test results of the unknown

Note: 1 These are test results from Experiment no. 4

IR Spectroscopy of Unknown Sample

104
102
100
98
96

% Transmittance

94
92
90
88
3800
3300
2800
2300
1800
1300
800
3550
3050
2550
2050
1550
1050
550

Absorbance

Figure 1. Infrared spectrum of unknown

Discussion
In this experiment, the unknown sample previously examined using qualitative tests in
experiment four was analyzed using Infrared spectroscopy. Infrared Spectroscopy is a
spectroscopy technique that uses infrared light to see at which wavelengths will the molecules
of the sample absorb or emit photons. Unlike the past qualitative tests where one separately
tests for the properties and functional groups present in the sample through reactions, infrared
spectroscopy gives us more detailed and faster results, considering that each functional group
varies at which wavelengths they can transmit (or absorb) light. A disadvantage in this
technique is that it cannot give an exact amount of each functional group present in the
sample.
This experiment utilized a KBr plate, where a few drops of sample was trickled in. The plate
was then placed inside the IR spectroscope for the machine and computer to compute for the
percent transmittance of the sample relative to the lights wavelength (as seen in figure 1).
The KBr plate was used in this experiment as it does not significantly affect the transmittance
and absorbance of light as it passes through the thin layer of the unknown. This is because
inorganic substances (i.e. KBr) prefer higher frequencies.
Based on figure 1, there are peaks ranging in between 1350-1450 cm-, 1600-1800 cm- and
2800-3000 cm-. The peaks in these intervals are at 1373.31 cm-, 1732.07 cm-, 2989.66 cm- respectively. According to the table of Characteristic IR absorptions of some functional
groups by McMurry. A strong peak found at approximately 1730 cm - indicates an aldehyde
carbonyl group (C=O). Moreover, according to a similar table made by Silverstain et. al., a
strong peak seen at 2850-3000 cm- implies the presence of a stretching C-H bond and a
variable peak at 1350-1480 cm- implies the presence of a bending -C-H bond. As seen in
figure 1, the extremum of the graphs can be found in these ranges. Thus, it can be said that the
unknown contains C-H and C=O bonds.
In experiment 4, based on the results on the table the unknown was suspected to be
acetaldehyde. This was concluded from the fact that the unknown tested positive for 2,4DNPH, chromic acid and Tollens test, tests that implies that the unknown is an aldehyde. The
unknown had also tested positive for the Iodoform test, which narrows the possibility of the
identity of the unknown to acetaldehyde. Acetaldehyde, is the only known aldehyde that tests
positive for the Iodoform test. To further confirm if the sample is indeed acetaldehyde, the
spectrum of the unknown could be compared to the IR spectrum of Acetaldehyde:

Figure
IRInfrared
SpectrumSpectrum
Figure2.2.Acetaldehyde
Acetaldehyde

Comparing these two spectra, one can see that there is a considerable similarity between their
peaks and behaviors as graphs. Both spectra are peaking at between 1350-1450 cm -, 16001800 cm- and 2800-3000 cm-. The carbonyl peak at the acetaldehyde spectrum is also peaking
at approximately 1700 cm-. However, there is a slight difference on the degree of
transmittance at the 2750-3000 cm-. The peak at the Acetaldehyde IR spectrum is lower as
compared to the transmittance of the unknown. However according to NIST, the acetaldehyde
IR spectrum from this collection were measured on dispersive instruments, often in carefully
selected solvents. Hence, the spectrum may differ in detail from measurements on FTIR
instruments or in other chemical environments. This explains that IR spectra of a compound
can differ based on the apparatus utilized, concentration and quality of the unknown and the
chemical environment of the test.
From the data and results established from the qualitative test results and IR spectrum,
it can be inferred that the unknown is an aldehyde. The conclusion that the unknown is
acetaldehyde still holds from the results in this experiment.
Conclusion
Based on the qualitative tests from the past experiment the identity of the unknown has been
suspected to be acetaldehyde. This inference has been further validated from the results of this
experiment as the unknown has been found to have C-H and C=O bonds. The C=O bond
particularly peaked at approximately 1730 cm-, the peak for an acetaldehyde carbonyl group.
The sample spectrum was also compared to an acetaldehyde IR spectrum and it has been
determined that the two spectra behaved similarly. However, there was a slight discrepancy at
2750-3000 cm-. This discrepancy has been attributed to several factors in the experiment
including the kind of instrument used and the chemical environment of the tests. Based on
these results, the objectives of this experiment which is to identify the bonds present on the
sampe and infer its identity was accomplished. Furthermore, it is recommended that to obtain
the conclusive identity of the sample an NMR Spectroscopy be run on the sample.
References
McMurry, J., Organic Chemistry. International ed. China: Brooks/Cole, Cengage Learning,
2012.

Silverstein, R.M.; Bassler, G.C.; and Morrill, T.C. Spectrometric Identification of Organic
Compounds. 4th ed. New York: John Wiley and Sons, 1981.
Smith, A.L. Acetaldehyde IR Spectrum. 1964. Evaluated Infrared Reference Spectra
Collection, Michigan. National Institute of Standards and Technology (NIST). Jpeg.
Oct 9 2016.
Smith, A.L., The Coblentz Society Desk Book of Infrared Spectra in Carver, C.D., editor, The
Coblentz Society Desk Book of Infrared Spectra, 2nd ed. Kirkwood, MO: The
Coblentz Society, 1982.