1

Differentiating Ketones, Alcohols, Aldehydes, and Esters through the use of

Dichromate Test, Tollens Test, Lucas Test, DNPH Test, Iodoform Test, and
Hydroxamate Test
Helen Rowi M. Tolentino, Jose Angelo S. Trinidad, Maria Cherisse P. Tuazon **, Maria
Christine P. Tuazon
College Of Science, Department of Biological Sciences, University of Santo Tomas, Espaa
Blvd., Manila
Abstract
This experiment seeks to differentiate the several types of oxygen-bearing organic compounds namely, n-propanol,
2-propanol, t-butanol, Formaldehyde, Acetone, Ethyl Acetate and an unknown sample by the use of specific
chemical tests; Dichromate Test, Tollens Test, Lucas Test, DNPH Test, Iodoform Test, and HydroxamateTest. The
researchers were able to characterize the unknown sample that was given to them through parallel chemical testing.
Keywords: Dichromate Test, Tollens Test, Lucas Test, DNPH Test, Iodoform Test, Hydroxamic Acid Test, npropanol, 2-propanol, t-butanol, Formaldehyde, Acetone, Ethyl Acetate

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,

where a carbonyl group is bonded to an alkoxyl (OR) group.

Several chemical tests were used to determine the nature of these standards. The first test
was the Dichromate Test, it is used to find out if there are compounds with reducing properties in
a solution. This test allows the convertion of primary alcohols to aldehydes and carboxylic acids
and secondary alcohols to ketones. The reagents used were

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

solid. The fourth test was the

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

and five drops of

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.

Results and Discussion

Tests
Dichromate

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

In the Dichromate test, n-propanol, a primary alcohol is oxidized to form an aldehydes,

while secondary alcohols are oxidized to ketones. The reagents contain

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.

In Tollens test, its reagent contains Ag( N H 3 2 OH which oxidizes Formaldehyde, an

aldehyde to a carboxylic acid, reducing silver ions to silver metal, thus producing a silver mirror
precipitate.

In Lucas Test, the reagent contains

alcohols like 2-propanol and t-butanol, in a

Zn Cl 2

in aqueous HCl, which reacts with some

S N 2 and S N 1

reaction which produces an alkyl

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 Dinitrophenylhydrazine (DNPH) Test, saturated compounds usually give off

yellow precipitates, while unsaturated or aromatic compounds give off red-orange precipitates.
Formaldehyde is a saturated compound that is why it was able to produce yellow precipitates.
While acetone, an aromatic ketone, and Ethyl Acetate, an unsaturated compounds both produced
red-orange precipitates which shows that they are positive for this test.

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.

In the Hydroxamate Test, esters when heated with hydroxylamine ( NH 2 OH ) form

+3
hydroxamic acids, which forms colored complexes with Ferric ( Fe

ions. Ethyl Acetate an

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