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YANZON, Janea Michaela B. Locker No.

40B
Experiment #4: Identification of an Unknown through Quantitative Analysis 26/03/19

Data and Results

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

5% NaHCO3
5% NaOH

5% HCl

H2SO4
Sample water Indications

toluene X X X X X
cyclohexene X X
t-butanol Base: amine
ethanol Acid: Carboxylic acid
Neutral, Ester, Alcohol, Amide,
acetone
Ether, Aldehyde, Ketone
Neutral, Alcohol, Ester, Amide,
ethyl acetate
Ether, Aldehide, Ketone
benzaldehyde X X X X
unknown X X Acid: Carboxylic acid

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
Yellow flame with
toluene - (purple)
soot/Unsaturated
Yellow flame without
cyclohexene + (brown)
soot/Saturated
Yellow flame with
t-butanol - (purple)
soot/Unsaturated
Yellow flame without
ethanol - (purple)
soot/Saturated
Yellow flame without
acetone - (purple)
soot/Saturated
Yellow flame without
ethyl acetate - (purple)
soot/Saturated
Yellow flame with
benzaldehyde + (brown)
soot/Unsaturated
Yellow flame without
unknown - (purple)
soot/Saturated
B. Lucas and Chromic Acid Tests
Observations/Indications
Sample
Lucas Test Chromic Acid Test
toluene - - (orange)
- (had a 2nd layer due to - (yellowish dark green due to
cyclohexene
solubility issues) hydrated benzene)
t-butanol - (clear) - (orange)
Ethanol - (clear) + (dark blue green)
acetone - (clear) - (reddish orange)
ethyl acetate - (clear) Partial reaction (dark brown)
- (had a 2nd layer due to
Benzaldehyde + (dark brown with precipitate)
solubility issues)
unknown + (white/milky, 2nd layer formed) - reddish orange color

C. Hydroxamic Acid and Iodoform Tests


Observations/Indications
Sample
Hydroxamic Acid Test Iodoform Test
- (didn’t turn red violet, more
toluene -
iron)
cyclohexene - (yellow orange) -
t-butanol - (white yellow) -
Ethanol - (yellow) + (yellowish precipitate)
Acetone - (bright yellow) +
ethyl acetate + (turned red violet) -
benzaldehyde - (yellow) -
Unknown - (light green) - (clear)

D. 2,4-DNPH and Tollen’s Tests


Observations/Indications
Sample
2,4-DNPH Test Tollen’s Test
toluene - (orange) - (slightly yellow)
cyclohexene - (insoluble orange) - (dirty yellow)
t-butanol - (orange) - (yellow)
ethanol - (orange) - (yellow)
acetone + (orange precipitate) - (yellow)
ethyl acetate - (orange) - (yellow)
benzaldehyde + (orange precipitate) + (silver mirror)
unknown - (no precipitate formed, orange) - (black)
E. Iron (III) Chloride and Alcohol Silver Nitrate Tests

Observations/Indications
Sample
Iron (III) Chloride Alcohol Silver Nitrate
toluene - + (clean layer)
cyclohexene - + (clean layer)
t-butanol - - (gold)
ethanol - -
acetone - - (yellow)
ethyl acetate - - (clear)
benzaldehyde - - (brown)
unknown - (yellow) - (clear)

Physical Properties of Unknown #21


Appearance: clear
Odor: pungent

Discussion

For this experiment, qualitative organic analysis tests were performed on different
samples and one unknown. These tests are used for identifying the different functional groups
present in a certain compound through properties such as solubility and reactivity with
different reagents as formation of precipitates and color changes). In the first day of this
experiment, the seven standard compounds (toluene, cyclohexene, t-butanol, acetone, ethyl
acetate, benzaldehyde and ethanol) were analyzed to see the positive and negative results and
other possible observations for these tests. After obtaining these results as a group, the
unknown sample was analyzed individually in day 2 of the experiment in order for its
functional groups to be identified. Through a process of elimination from a list of possible
compounds, the identity of the unknown is determined. The tests are categorized into two: the
solubility tests and the functional group tests.

The only test the unknown sample was positive in was the Lucas Test which was
indicated by the formation of a 2nd layer. This indicates the presence of a secondary alcohol
(AtQ<1>). Cross-referencing all the tests, the unknown sample is most probably propanal
(AtQ<2>). The limitations of these qualitative tests is that it would be difficult to know the
true structure of the compound because these tests can only detect certain functional groups.
Specific structures cannot be seen and the only way to narrow down the possible chemicals is
to give a set of standards something to compare with or a set of chemicals with which one of
them is surely the unknown sample (AtQ<3>). Modern analytical techniques like infrared
spectroscopy would give the same information as qualitative tests. They also provide
information on the presence of certain functional groups. It would also be more precise in
finding out what kind of functional group is present since it deals with specific wavelengths
and measurements. Qualitative tests are also subject to human error and also, subjectivity in
observing indicators such as formation of precipitates and reactions happening (AtQ<4>).

Sample Calculations
none

References

Most CF. Experimental Organic Chemistry. USA: Wiley & Sons; 1988. Palleros DR.
Experimental Organic Chemistry. USA: Wiley & Sons; 2000.
Organic Chemistry Teachers’ Association (OCTA). A Laboratory Manual of Basic Chemistry.
Philippines: Graphic Arts; 1973.

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