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Compound ID Lab Report

March 7, 2023

Noor R.

Introduction

64 unlabelled barrels filled with organic compounds were found in an illegal dump in Pierce
County and the Environmental Services Division decided to give these barrels to UWT chemists
to identify the unknown organic compounds.

Abstract

This lab aimed to identify the unknown compounds that were found in the barrels dumped
illegally by using various methods such as Mass Spectrometry (MS), Nuclear Magnetic
Resonance Spectroscopy (NMR), and Infrared Spectrometry (IR). Therefore the structures of the
organic compounds were obtained and the unknowns were identified. Unknown S2 turns to be
cinnamic acid and unknown L5 turns to be benzylamine.

Experimental

A sample of solid unknown S2 was taken and put into a small tube then placed in the Vernier
Melting Point apparatus. The melting point was measured to be 133°C-137°C. Another sample
of the unknown was dissolved in water and the pH test strip was dipped into the solution to test
for the acidity, the pH value was measured to be 5. Unknown S2 was also tested with 𝑁𝑎𝐻𝐶𝑂3

for carboxylic acid presence. A sample of the unknown was placed in a tube and added a couple
drops of 𝑁𝑎𝐻𝐶𝑂3 solution to it and waited for the 𝐶𝑂2to take place. The test resulted negative

and the 𝐶𝑂2 gas wasn’t produced. The solid sample was run throught Perkin Elmer Spectrum

100 to measure its IR spectrum, and again run through the Mass Spectrometer instrument to
measure its mass spectrometry. Additional tests were performed: solubility test, the solid was
slightly soluble in water but mostly insoluble, and Iron Chloride test (𝐹𝑒𝐶𝑙3) to test for phenol

which turned out negative.

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For the second unknown, liquid L5, a sample was placed in Abbe-3L Refractometer instrument,
the refractive index was measured to be 1.5855. Another sample of the liquid was placed in a
tube and couple drops of 𝑁𝑎𝐻𝐶𝑂3was added to the tube to test for carboxylic acid presence, the

result turned out negative and no clue of carboxylic acid existed. 𝐴𝑔𝑁𝑂3 test was done on the

unkown to test for halides presence in the sample, the result showed no reaction. The pH of the
unknown was also measured by placing 10 drops of the liquid on a pH strip, the strip changed
color to orange and the pH measured to be 4. The solubility of the compound was tested and the
result showed no solubility in water. The liquid was run through Perkin Elmer Spectrum 100 to
measure its IR spectrum, and again run through the Mass Spectrometer instrument to measure its
mass spectrometry.

Result & Discussion

Unknown Solid S2

The results of the tests done were a bit contradicting each other. The pH test read that the
unknown was a weak acid. However, the 𝑁𝑎𝐻𝐶𝑂3 was negative (no reaction) which means the

compound wasn’t containing any carboxylic acid. The IR Spectra on the other hand showed a
−1 −1
broad peak between 2500𝑐𝑚 and 3000𝑐𝑚 which was an indicator of carboxylic acid
presence (Figure 1). 𝐹𝑒𝐶𝑙3 reaveled no phenols in the compound so this was useful piece to

eliminate one possibility from the possible structures that were expected. The 13C-NMR showed
7 different carbon environments and the chemical shifts were between 119 ppm and 180 ppm
(Figure 6). The chemical shift at 175ppm indicated a carboxylic acid presence which agreed with
the IR Spectra. The chemical shifts around 130ppm indicated the presence of C=C double bond
and a benzene ring (Figure 9). With all the information collected, several structures were drawn
to see the probabilities and the best fit was to be cinnamic acid. It had one benzene ring with
C=C double bond and a carboxylic acid, 7 different carbon environments that are shown on the
structure and on the 13C-NMR. The H-NMR showed 5 hydrogen environments which
contradicted the structure that had 6, but this was reasonable because the instrument used for the
H-NMR wasn’t as precise. The measured melting point of the unknown started at 133°C and the
cinnamic acid has a melting point of exactly 133°C (PubChem). The mass spectra also played a
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useful role in making sure the unknown is cinnamic acid; when the structure of cinnamic acid
was drawn (Figure 1), the formula was discovered and the molecular mass was caculated to be
148g/mol which is the same m/z value shown in mass spectrum (Figure 5).

Unknown Liquid L5

Most of the tests done on this unknown lead to reasonable results; the 𝑁𝑎𝐻𝐶𝑂3 was negative,

there wasn't any presence of carboxylic acid. And the IR spectra also didn’t show any possibility
of carboxylic acid bonds stretches (Figure 2). The 𝐴𝑔𝑁𝑂3 test was also negative and no clue of

halides present in the unknown. These results made it easier to limitate the possibilities of the
−1 −1
groups present in the compound. The IR showed a small curvy peak at 3300𝑐𝑚 - 3500𝑐𝑚
which was an indicator of N–H bond stretch that was likely an amine group (Figure 2).
Nevertheless, the pH test resulted in a value of 4 and this meant the compound was acidic which
contradicted the presence of amine group. But it’s possible that the test was run wrongly or the
pH paper wasn't precise because normally it wouldn’t be as accurate as a pH meter (Atlas
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Scientific 2021). The IR also reveals other short peak at 3000𝑐𝑚 for Ar–H bond stretching and
−1
strong peaks at 1600𝑐𝑚 for C=C stretching (Figure 2). Based on these information from the IR
and the tests done, a structure of benzylamine was drawn and turns out to be the most likely
structure when compared to the spectras obtained. First, the 13C-NMR showed 4 carbon
environments as well as the structure (Figure 8). The chemical shifts narrowly ranged from
115ppm to 150ppm. The chemical shift on 115 indicates the presence of nitrogen and the
chemical shift on 130 indicate a benze ring (Figure 9). The molecular mass of the identified
compound was calculated and was 93 g/mol, this was reasonable since the mass spectra also
showed a m/z value of 93 (Figure 7). H-NMR spectra of the unknown presented 4 hydrogen
environments (Figure 3) which resonated with the number of hydrogen environments of
benzylamine structure (Figure 2). And refractive index was also used to make sure that the
unknown is benzylamine. The refractive index of the unknown on room temperature (18.7°C)
read 1.5855, the value is slightly higher than the benzylamine refractive index that is known to
be 1.543 (Wikipedia). But this difference is okay since high temperature lowers the refractive
index value, and lower temperature raises the value (UTSC). So it was expected that the
refractive index would be slightly higher because the room temperature was low.
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Conclusion

For solid unknown S2, the IR spectra, Mass Specta, 13C-NMR, melting point and pH tests all led
to a reasonable structure that is cinnamic acid. Only the 𝑁𝑎𝐻𝐶𝑂3 was negative which didn’t

indicate the presence of carboxylic acid and it was possibe that the test was run in a wrong way
or the tube was contaminated.

For liquid unknown L5, there was also one test that contradicted the other data collected; the pH
test that resulted in a value of 4. And this can be explainable because the pH strips are not always
precise. Luckily, the other data like IR spectra, Mass Spectra, 13C-NMR, H-NMR, and 𝑁𝑎𝐻𝐶𝑂3

were all reasonable and led to a similar structure which was considered conclusive.
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References

National Center for Biotechnology Information. "PubChem Compound Summary for CID
444539, Cinnamic acid" PubChem,
https://pubchem.ncbi.nlm.nih.gov/compound/Cinnamic-acid.

Benzylamine, “Wikipedia”, last edited on 5 January 2023. Benzylamine - Wikipedia

Refractive Index Theory, “University of Toronto Scarborough UTSC” , Chemistry Online @

UTSC (utoronto.ca)

“pH Meter Vs pH Paper: Which one do you need?” Atlas Scientific, September 17, 2021
(atlas-scientific.com)