You are on page 1of 6

Qualitative Organic Analysis: Identification of Two Unknowns

Amber Bolden
November 30, 2015
CHEM 2411-002
The determination of unknown compounds can be difficult when general physical
characteristics such as melting points, are tested. With a more complex qualitative analysis, such
as an Infrared spectroscopy, which is unique to each compound, or a Proton Magnetic
spectroscopy, similar compounds can be identified. With the use of infrared spectroscopy, the
organic compound will absorb the infrared radiation that corresponds in energy to its own
vibrations. This allows for an induced vibrational excitation of covalently bonded atoms and
group, which is unique to each bond, and able to be identified in a spectra graph. (1) Similarly,
with Proton Magnetic Resonance, protons of the compound are first excited and the light they
emit as they return to their lower energy state indicates the protons specific magnetic field
determined by both its unique magnetic field produced by electrons near the nucleus, and its
magnetic field produced from neighboring nuclei, which correlates to a specific wavelength able
to be analyzed by PMR. The purpose behind the qualitative organic analysis experiment is allow
the chemists to practice multiple methods of technique to determine an unknown compound.
Utilizing these technique allows for the chemist to be firmer in his or her identification of the
unknown; there is specific data for each unknown, and multiple tests, which allow for more
detailed results and elimination of other compounds and more vague results.
Results and Calculations
Melting Point/ Boiling Point:
Melting Point Of Solid Unknown 181
First drop: ~115 C
Solubility test:
Ethyl Acetate
5% HCl
10% NaOH
5% NaHCO3
Concentrated Sulfuric

Solubility of Solid
Unknown 181
Not Soluble
Not Soluble
Not Soluble
Not Soluble

Beilstein test:
Flame Color of Solid Unknown 181
Orange flames no halogen
Sodium Fusion and Test For Elements:

Boiling Point of Liquid Unknown 97

~115 C
Solubility of Liquid
Unknown 97
Not Soluble
Not Soluble
Not Soluble
Not Soluble
Soluble, not miscible

Flame color of Liquid Unknown 97

Orange flames no halogen

Color Present for Solid Unknown 181

Blue indicating the presence of Nitrogen

Color Present for Liquid Unknown 97

Negative for all test

Infrared (IR) Spectroscopy (2),(3),(4)

Functional Groups for Solid Unknown 181
N-H: ~3300cm-1
C-H aromatic indication: ~3200-3000 cm-1
C=O: ~1675 cm-1 (amide)
C=C: ~1600-1550 cm-1 (aromatic)

Functional Groups for Liquid Unknown 97

C-H aromatic indication: ~3100-3000 cm-1
C=O: ~1700-1675 cm-1 (ketone)
C=C: ~1600-1575 cm-1 (aromatic)
-CH3 aromatic indication: ~1375 cm-1 (bend)

Proton Magnetic Resonance

Hydrogen for Solid Unknown 181
Aromatic H: ~7.6-7.0ppm
Carbonyl peak: ~2.2ppm

Hydrogen fro Liquid Unknown 97

Aromatic H: ~7.4-7.2ppm
Carbonyl peak: ~2.5ppm

Experimental Methods
Part I: Melting Point/ Boiling Point Determination
First, the melting point of the solid unknown 181 was recorded. Next, ~1.0-2.0mL of the
unknown liquid 97 was added to a clean test tube along with a boiling stone and a thermometer
stationed ~1.0cm above the liquid, then placed in a heating mantle, where sand was added, and
the boiling point of the liquid unknown 97 was recorded.
Part II: Solubility Tests
~2.0mL of the solvents, ethyl acetate, water, 5% HCL, 10% NaOH, 5% NaHCO3, and
concentrated sulfuric acid, were added to separate test tubes, 1 set for the solid unknown 181 and
1 set for the liquid unknown 97, where ~1 drop of the unknown liquid 97, and ~3-4 small crystals
of the unknown solid 181 were added to each and analyzed.
Part III: Beilstein Test
A piece of copper wire was heated over a Bunsen burner to be cleaned, and once cooled a small
amount of each unknown was added to the wire, under separate trials. With the addition of the
unknowns the wire was then heated and the color of the flame was recorded.
Part IV: Sodium Fusion and Tests for Elements
A small spatula tip of the solid unknown 181 was added to a clean test tube and labeled, then
placed into a 50mL beaker also labeled with name and unknown number. The same procedure
was applied to the liquid unknown 97, with ~2-3 drops. Both samples were submitted to the
teachers assistant (TA) who performed the test. She would obtain a pea sized piece of sodium on
a spatula, rinse it over a beaker with a small amount of hexane, the carefully ad the sodium metal
to the test tube so that it remains stuck to glass near the top of the tube. Next she heated the top
of the test tube using a Bunsen burner so that the sodium melts, into a ball and rlls into the
sample. After allowing the test tube to cool she carefully added methanol. Gently heated the test
tube over a Bunsen burner, and once the reaction was complete she carefully broke the test tube
into its corresponding 50mL beaker, containing 10mL of distilled water. With the new sample,
the nitrogen test, sulfur test, the halide test, and the halogen differentiation of chloride, bromide,
and iodide test were performed.

Part V: Infrared (IR) Spectroscopy

The IR spectra for the solid 181 and liquid 97 unknown was analyzed, and major identifying
peaks were labeled, with corresponding functional groups indicated.
Part V: Proton Magnetic Resonance (PMR) Spectroscopy
The PMR spectra for the solid 181 and liquid 97 unknown was analyzed and each peak was
explained by chemical shift, integration, and splitting for each proton it corresponded to.
Throughout the initial steps within the procedure not much information was able to be
obtained, as the possible unknowns for both solid and liquid (Table 1.1 and 1.2), had very similar
melting/ boiling points. More problems were encountered during the solubility tests, with respect
to the solid, because it seemed to partially dissolve, but this was unclear. From these results, both
solid unknown 181 and liquid unknown 97 seemed to be non-polar molecules; however, the solid
unknown structure was unclear in its polarity. During the Beilstein test, at one point the flame of
the solid unknown turned green, but after multiple trials, both the solid unknown 181 and liquid
unknown 97 proved negative. More clear results were provided during the sodium fusion test, for
the solid unknown, which showed blue, indicating the presence of nitrogen. The liquid unknown
97 was negative for all results.
The infrared spectra graph of both unknowns proved to be the most useful, when
attempting to decipher which of the possible unknowns were compound 181, and 97. For the
liquid unknown 97, there were heavy indication of aromatic bonding, with carbon and hydrogen
alike. This narrowed the possible compound to 3-(trifluoromethyl)acetophenone and
Acetophenone. Fortunately, since the liquid unknown 97 was negative for all of the sodium
fusion tests and the Beilstein test, it was clear that there was no halogen present, which left
Acetophenone as the best possible compound for liquid unknown 97.
The solid unknown 181 was more difficult to decipher based on the infrared spectra, but
it still narrowed the results down. With the heavy indication of aromatic bonding, the best
possible compounds would be 4-aminobenzamide, acetanilide, N-benzylcrotonamide, and 2chlorobenzanilide. Since the solid unknown 181 was negative for the remaining sodium fusion
tests, and was negative for the Beilstein test, 2-chlorobenzanilide was able to be eliminated.
Based on the graph, it was hard to decipher which type of N-H bond was present, but based on
the wavelength parameters and weaker absorption, a single -N-H bond, seemed more likely than
a H-N-H bond, which helped eliminate N-benzylcrotonamide. The final two compounds are very
similar, in that they differ in the amount of carbons and hydrogens present. Firstly, due to the
Infrared graph, there did not seem to be a standard C=C bond which would occur in the 16801600 cm-1 range, rather an aromatic C=C bond was present. (5) Likewise, on the proton magnetic
resonance graph there were not as many peaks, indicating a smaller amount of hydrogen present,
which would also favor acetanilide, over 4-aminobenzamide. (6) Therefore, under these
conditions, acetanilide seemed the best possible compound for solid unknown 181.

tm (accessed 2015)
(2) (accessed 2015)
(3) (accessed 2015)
(4) Pavia, D. L.; Lampman, G. M.; Kriz, G. S.; Engel, R. G. Experiment 55. In Introduction
to organic laboratory techniques: a small-scale approach; Thomson Brooks/Cole:
Belmont, California, 2005; pp 168260.
(5) (accessed 2015)
(6) (accessed 2015)
"On my honor, I pledge that I have neither given nor received help on this assignment."
Honor Pledge: _______________________________________________________________

Table 1.1: Unknown Compound 97

Possible Compound for Liquid
Unknown 97







Ethyl levulinate


Table 1.2: Unknown Compound 181

Possible Compound for Solid Unknown




Ethyl oxamate


Dihydroacetic acid monoanilide