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Margarita Maria Isabella V.

Saulog March 22, 2017


Experiment 5: Identification of an Unknown through Qualitative Analysis Locker 17C

Results

Physical Properties of the Unknown:


Appearance: clear, colorless liquid
Odor: citrus-like odor

Table 1. Solubility Test Results of the Unknown and Functional Group Standards.

5% NaHCO3
5% NaOH

5% HCl

H2SO4
water

Sample Indications

Note: Indicate solubility/miscibility with an X


(see example). For samples soluble in water,
indicate A if acidic to litmus, B if basic to
toluene X X
litmus, and N if neutral to litmus.
Indicate the implications of the results (i.e.
phenol).
Cloudy white mixture insoluble in water,
cyclohexene X
change in color in H2SO4 test Alkene
Slightly cloudy mixture insoluble in water,
t-butanol X
change in color in H2SO4 test Alcohol
Clear homogeneous mixture soluble in water,
ethanol N no bubbles formed in NaHCO3 test Low mol.
Mass Alcohol
Cloudy homogeneous mixture soluble in
acetone A X water, no bubbles formed in NaHCO3 test
Ketone
Clear homogeneous mixture soluble in water,
ethyl acetate A X bubbles formed in NaHCO3 test Carboxylic
Acid
Clear homogeneous mixture soluble in water,
benzaldehyde A
no bubbles formed in NaHCO3 test Aldehyde
Cloudy mixture insoluble in water, change in
unknown X
color in H2SO4 test - Alkene

Table 2. Functional Group Test Results of the Unknown and Functional Group Standards.

A. Ignition and Bayer Tests

Observations/Indications
Sample
Ignition Test Bayer Test
Flame with black smoke
cyclohexene Red brown precipitate alkene
Unsaturated compound
t-butanol Flame with no smoke saturated Purple solution, no precipitate
compound
No flame with no smoke
ethanol Purple solution, no precipitate
saturated compound
No flame with no smoke
acetone Purple solution, no precipitate
saturated compound
No flame with no smoke
ethyl acetate Purple solution, no precipitate
saturated compound
Flame with black smoke Brown solution, cloudy with slight
benzaldehyde
Unsaturated compound precipitate - alkene
Flame with black smoke
unknown Red brown precipitate alkene
Unsaturated compound

B. Lucas and Chromic Acid Tests

Observations/Indications
Sample
Lucas Test Chromic Acid Test
nd
cyclohexene Cloudy colorless, no 2 layer Dark red solution, no precipitate
2nd layer formed on surface, formed
t-butanol Dark red solution, no precipitate
immediately tertiary alcohol
Dark blue-green precipitate
ethanol No 2nd layer formation
primary alcohol
acetone No 2nd layer formation Dark red solution, no precipitate
nd
ethyl acetate No 2 layer formation Dark red solution, no precipitate
Yellowish precipitate formed, no 2nd
benzaldehyde Dark yellow solution, no precipitate
layer formation
Dark yellow-brown solution, no
unknown No 2nd layer formation
precipitate

C. Hydroxamic Acid and Iodoform Tests

Observations/Indications
Sample
Hydroxamic Acid Test Iodoform Test
Clear, colorless solution, no
cyclohexene Yellow solution
precipitate
t-butanol Yellow solution Clear solution, no precipitate
Clear, yellowish solution, no
ethanol Yellow solution
precipitate
Yellowish precipitate formed
acetone Yellow solution
Methyl ketone
Clear, yellowish solution, no
ethyl acetate Purple solution Ester
precipitate
Clear, yellowish solution, no
benzaldehyde Light yellow solution
precipitate
Clear, yellowish solution, no
unknown Light yellow solution
precipitate

D. 2,4-DNPH and Tollens Tests

Observations/Indications
Sample
2,4-DNPH Test Tollens Test
cyclohexene Orange solution, no precipitate Clear, no silver mirror
t-butanol Orange solution, no precipitate Clear, no silver mirror
ethanol Orange solution, no precipitate Clear, no silver mirror
acetone Yellow precipitate Ketone Clear, no silver mirror
ethyl acetate Orange solution, no precipitate Clear, no silver mirror
Yellow-orange precipitate
benzaldehyde Silver mirror formed - Aldehyde
Aldehyde
unknown Orange solution, no precipitate Clear, no silver mirror

Postlab Questions

1. Summarize the results obtained from the unknown. Which tests had positive results on the unknown
sample? What do these results indicate?
- Among the qualitative tests done to obtain the identity of the unknown, the Baeyer test was the
only test to produce a positive result. A positive result for the Baeyer test would thus indicate the
presence of an alkene in the structure. The ignition test also gave a positive result because of the
presence of a black sooty smoke, thus the unknown is also identified to be an unsaturated
compound. Among the solubility tests performed, the insolubility of the unknown in water lead
to a positive result or change of color in the H2SO4 test. This would show that the unknown in
soluble in H2SO4 and it would confirm that the present functional group is alkene.

2. Based on the indications of the different qualitative tests and the physical properties of the
unknown, what is the identity of the unknown sample?
- After reviewing the different properties of the given possible identities, it can be said that the
unknown sample is Limonene. This is indicated by the positive result in the Baeyer test, the
solubility of the unknown in H2SO4, and the citrus-like odor it has.

3. What are the limitations of the qualitative tests? Can qualitative tests ascertain unknown
samples? Explain.
- Although qualitative tests allow for quick and easy assessments of compounds, it proves to be
difficult in terms of evaluating reactions accurately and precisely. With the great subjectivity
involved in qualitative tests, it is hard to ascertain the results of tests because of the variability in
seeing and observing the reactions. These tests are also difficult to reproduce and the results may
vary for each time. Human error is also increased when it comes to qualitative tests because
exact measurements and instructions arent always followed. Therefore, qualitative tests are one
way of obtaining information about unknown samples and functional groups, but they should
not be used alone in determining the identity of unknown samples. It is much more accurate to
use the results of both qualitative tests and modern analytical tests to accurately determine the
identities of unknowns.

4. What modern analytical technique would give the same information as the qualitative tests?
What are the advantages of this technique over the qualitative tests?
- Spectral identification is one modern analytical technique that would provide the same
information as qualitative tests. In spectral identification, infrared spectrums are produced
during the interaction of molecules of the substance with infrared radiation. These spectrums
show peaks and troughs that can have a corresponding frequency related to a certain functional
group. Thus, spectral identification also determines which functional groups are present in the
sample. IR spectroscopy has many advantages over qualitative tests. One of which is that it can
be tested in any state and more information can be obtained from the results, such as
information regarding the molecular structure, number, and position of substituents. It can also
obtain information fast and efficiently. Nuclear magnetic resonance is also another technique
used wherein the substance is placed in a magnetic field and subjected to an electrical signal.
The peaks formed are what help determine the functional groups present. Mass spectrometry
helps in identifying the mass of the substance and how their atoms are joined together. This
technique also provides the molecular weight.

References

- Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City: Office of
Research and Publications, Ateneo de Manila University; 2005.
- Nguyen DH. Sciencing [Internet]. USA: Leaf Group, Ltd.; unknown first publication [cited
2017 March 21]. Available from: http://sciencing.com/drawbacks-qualitative-evaluation-
chemistry-experiments-11336.html
- [Author Unknown]. Chemistry: LibreTexts [Internet]. USA: UC Davis; unknown first
publication [cited 2017 March 21]. Available from:
https://chem.libretexts.org/Core/Organic_Chemistry/Spectroscopy/Infrared_Spectroscopy