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Introduction
The Differentiation of Oxygen-bearing compounds was used to identify what functional
group is present in a solution. It also focused on identifying the kind of alcohol, whether it may
be primary, secondary or tertiary. Standard compounds were used as guides to identify the
characteristics of each of the compounds present.
Functional groups are specific and common arrangements of atoms that impart
predictable properties and reactivity to a certain molecule. The Alcohols used in the experiment
were n-propanol, 2-propanol, and t-butanol. The Alcohol Family is
characterized by having a hydroxyl (-OH) group attached to a carbon
atom.
Next is the Aldehyde and Ketone groups, in which Formaldehyde and Acetone
were
used as examples. Aldehydes and Ketones both contain a carbonyl group where a
carbon atom has a double bond to its oxygen. Another functional group
that
was identified was the Ester group, represented by Ethyl Acetate also known as
ethyl ester. Esters are characterized by having its general formula of RCOOR,
K 2 Cr 2 O7
and
H 2 S O 4 . The
second test was Tollens Test, it is used to detect if there is the presence of aldehydes in the
solution. As the name suggests, the reagent used is the Tollens reagent. The third test was the
Lucas Test that differentiates primary, secondary from tertiary alcohols. They differ in their
reactions with the reagents used, which are HCl and
Zn Cl 2
DNPH Test which able to detect if a carbonyl group or Ketone is present. Specific reagents that
were used in this test were Ethanol and the DNPH reagent. The fifth test was the Iodoform Test,
where secondary alcohols with methyl groups are oxidized to methyl ketones. The reagents
during this test were KI and NaOCl solution. And lastly, the Hydroxamate Test was done for the
determination of the presence of Esters in the solution. The reagent used was Hydroxylamine
hydrochloride in ethanol.
This experiment seeks to differentiate the several types of oxygen-bearing organic compounds
and to identify an unknown sample by the use of specific chemical tests.
Methodology
For the Dichromate Test, from the given unknown sample and the standard, eight drops
from each were placed in separate test tubes. Two drops of 10%
6M
H 2 S O4
K 2 Cr 2 O7
were added then mixed. The product produced would tell if the unknown sample
is oxidizable or non-oxidizable.
For Tollens Test, five drops of the unknown sample and standard in separate test tubes
were placed in separate test tubes. 2ml of Tollens reagent was then added. After doing so, the
solution was left to stand for 5 minutes. If ever there was no production of silver precipitate, the
test tube was placed into a 70 C water bath for 5 minutes.
For Lucas Test, five drops of the unknown sample and the standard in separate test tubes.
Then these were added with fifteen drops of conc. HCl and a corn-grain amount of
Zn Cl 2
solid. The test tubes were shaken well while the time it took for the appearance of turbidity was
recorded.
For the DNPH Test, five drops of the unknown sample and standard were placed in
separate test tubes. 1ml of Ethanol, and 1 ml of DNPH reagent were then added. The solution
was left to stand for 15 minutes. If ever there was no precipitate formed, the test tube was placed
into a 70 C water bath for 15 minutes.
For the Iodoform Test, five drops of the unknown sample and standard were placed in
separate test tubes and were then added with 20 drops of 10% KI and 20 drops of NaOCl
(Chlorox). If ever there was no precipitate formed, the test tube was placed into a 70 C water
bath for 5 minutes.
For the Hydroxamate Test, three drops of the unknown sample and standard were placed
in separate test tubes and the added with 1ml of 0.5M hydroxylamine hydrochloride in ethanol.
The solution was the heated to reflux for 5 minutes and was later left to cool in room
temperature. 2 to 5 drops of 5% ferric chloride was then added to the solution.
npropanol
blue
solution
2propanol
blue
solution
t-butanol
orange
solution
Tollens
Lucas
colorless
solution
turbid
solution
(slow)
Acetone
orange
solution
silver mirror
ppt
colorless
yellow
ppt
redorange
ppt
Ethyl
Acetate
blue
solution
Unknow
n
orange
solution
redorange
ppt
redorange
ppt
redpurple
solution
yellow
solution
turbid
solution
(fast)
DNPH
orange
solution
Iodoform
colorless
solution
Hydroxamat
e
Formaldehyd
e
blue
solution
yellow
ppt
yellow
solution
yellow
solution
Cr O3 in a sulfuric
acid solution which is made up of both Chromium 6+ and Chromium 3+. Chromium 6+ is
orange resulting to a negative reaction. While Chromium 3+ is blue-green giving a positive
result. When an oxidation reaction occurs the solution will turn blue or if not, it will show
otherwise.
Zn Cl 2
S N 2 and S N 1
chloride. Which first forms when the solution appears cloudy of turbid. The reaction also differs
in the time when the appearance of turbidity occurs for different alcohols respond to
Zn Cl 2 in
different rates. The test is positive for both secondary and tertiary alcohols while it is negative
with primary alcohols.
secondary alcohol
tertiary alcohol
alkyl chloride
alkyl chloride
In the Iodoform Test, methyl ketones are identified. It uses a haloform reaction. A
haloform is produced by the halogenation of a methyl ketone. In this test Acetone, a methyl
ketone was oxidized to a carboxylic acid and an iodoform, a yellow precipitate.
ester was heated with hydroxylamine and showed a red-purple solution, meaning it is positive for
the test.
For the Unknown sample, the researchers compared and contrast the results gathered
from the sample with the results from the other organic compounds. According to the results, the
unknown was positive in the DNPH test, showing that a Ketone is present in the solution. It also
showed that it was negative in the Dichromate Test. Based on these observations, the unknown
sample is Acetone.
Conclusion
The various types of Oxygen-bearing organic compounds were successfully differentiated
with the use of several chemical tests. The Dichromate Test is used to determine whether a
solution is oxidizable or non- oxidizable. Whereas, the Tollens Test indicates if the solution is an
Aldehyde or a 1 / 2 Alcohol. Lucas Test on the other hand determines whether the solution is a
2 or 1 Alcohol. While the DNPH Test shows if the solution is a Ketone or a 3 Alcohol. The
researchers identified the unknown sample as Acetone.
References
Ebbing, D. & Gammon, S. (2016). General Chemistry (11th ed.). New York, NY:
Cengage Learning
Fryle, C. & Solomons, T.W. (2014). Organic Chemistry (11th ed.). New Jersey, Hoboken: John
Wiley & Sons, Inc.
Hoffmann, R. (2004). Organic Chemistry: An Intermediate Text (2nd ed.). New Jersey, Hokoben:
John Wiley & Sons, Inc.
Winter, A. (2005). Organic Chemistry I For Dummies. New Jersey, Hoboken: John Wiley &
Sons,
Inc.
Chemical Tests for the Unknown.(2007, April 07). http://cactus.dixie.edu/smblack/chemlabs/
chemical_tests_for_unknowns.pdf
One Part of Chemistry: Reactions of Aldehydes, Ketones And Phenols (2011, September 19).
http://1chemistry.blogspot.com/2011/09/reactions-of-aldehydes-ketones-and.html
Organic Qualitative Analysis. (2009, September 21). http://www.foothill.edu/psme/armstrong/
pdfdocuments/qualanal.pdf