CLASSIFICATION TESTS FOR CARBOXYLIC ACID AND ITS DERIVATIVES

Yya Cabauatan, Denise Caramoan, Christine Cerrero, Christopher Cipriano, Joshua Adrian Crisostomo,
Joseph Cua
Group 2, 2F-PH, Department of Pharmacy, Faculty of Pharmacy
ABSTRACT
Carboxylic acid and its derivatives include classification tests being the following: aminolysis,
alcoholysis, and the hydroxamic acid test. Acetyl chloride, acetic anhydride, benzamide, and ethyl
acetate were the samples used for the carboxylic derivatives. Said compounds went through
classification tests that were set for each of them such that acetyl chloride and acetic anhydride was
subjected to hydrolysis, aminolysis, and alcoholysis ; ethyl acetate to hydrolysis and hydroxamic acid
test ; benzamide to hydrolysis ; acetamide to the hydroxamic acid test. Positive results of the following
tests equated to the following: carboxylic acid formation through hydrolysis, ester formation through
alcoholysis, amide formation in aminolysis, and deep burgundy discoloration in hydroxamic acid test
showing the presence of hydroxamic acid.
INTRODUCTION
Carboxylic acids are said to be the most
abundant of organic compounds that they could
be found in living things as well as in the
laboratory samples that are being used. Amides,
acid anhydrides, acid halides, and esters are
some of the many types or kinds of the
carboxylic acids. They are important, also, in
the sense that they are utilized by living
organisms, as well as us, humans, in factory
productions. Common feature of all carboxylic
acids is that contain acyl group(s) bonded to the
electronegative atom or substituent that acts as a
leaving group in the substitution reactions,
replacing the OH group of carboxylic acid.
Being strong organic acids, these compounds
react with silver nitrate and sodium carbonate to
create or form their corresponding carboxylate
salts.
Reactions that are common to the
carboxylic derivatives are the following:
substation by water through hydrolysis to yield
an acid, alchohol by alcoholysis to yield an
ester, amine by aminolysis to yield an amide,
hydride to yield an alcohol by reduction, and by
organometallic reagent to yield an alcohol
through the Grignard reaction.

Upon reaction with water, the carboxylic

acid derivatives yield the parent carboxylic acid.
Furthermore, provided that a derivative is more
reactive than the other, can be converted into
another substance.
The objectives of the experiment are the
following: differentiate reactivity of the
derivatives, distinguish derivatives using the
classification tests, and to further explain
through the use of chemical equations and
mechanism the reactions that were utilized in
the tests.
METHODOLOGY
The samples that were used in this
experiment are the following: acetyl chloride,
acetic anhydride, ethyl acetate, acetamide, and
benzamide.
A. Procedure
1.) Hydrolysis of Acid Derivatives
The hydrolysis of the acyl halides and
acid anhydride was done by placing 1ml of
water into two different test tubes. Then, 10
drops of acetyl chloride and acetic anhydride
were carefully dropped into each test tubes. The

reaction produced an exothermic reaction,

making the test tubes feel warm. The following
solution was then divided into 2 portions. 1mL
of 2% AgNO3 was added to one portion that
resulted to precipitation and 1mL of NaHCO3 to
the other portion that resulted to an evolution of
gas. An mL of ethyl acetate was utilized for the
hydrolysis of the esters. The esters were added
2mL of 25% NaOH. Afterwards, it was covered
and heated with a water bath. Then, the solution
was made neutral with the addition of 10% HCl.
This resulted to a particular odor that was taken
note of having distinguished it by the wafting
motion.
On the hydrolysis of amides, a small
amount of benzamide was added with 5mL of of
10% NaOH that was then boiled. A moist red
litmus paper was then used to test for the
evolution of gas.
2.) Alcoholysis: Schotten Baumann
Reaction
A mixture was made using 10 drops of
acetic acid, 1mL of ethanol, and 5 drops of
concentrated H2SO4. This mixture was warmed
using a water bath in the span of about 2
minutes. An odor of ester was distinguished and
recorded.
Another mixture involved 0.5mL of
ethanol, 1mL of water, 0.2mL of acetyl chloride,
and 2mL of 20% NaOH was added together.
This mixture that was placed in a test tube was
then stoppered with parafilm after which the
solution was shaken for several minutes. An
odor of ester was formed together with 2 layers
forming in the test tube.

4.) Hydroxamic Acid Test

2mL of alcoholic NH2OH.HCl and 1mL
of KOH was put together with 2 drops of ethyl
acetate and acetamide. This mixture was heated
to a boiling water bath for a few minutes. It was
later cooled and then 1mL of 5% FeCl3 was
added. A deep burgundy color was formed
indicating a positive result.
RESULTS AND DISCUSSION
In hydrolysis of acyl halides and acid
anhydrides, warming effect was observed
because of the exothermic reaction and acetic
acid formation brought about by the parent
carboxylic acid. CO2 gas was the result of the
evolution of gas when an effervescence
occurred on the addition of 2% AgNO3 and
saturated NaHCO3 to acetyl chloride.
25% NaOH, an aqueous base, was used
to hydrolyze ethyl acetate resulting to acetic
acid with alcohol that has a plastic balloon-like
odor.
Upon heating in 5mL of 10% NaOH
solution, benzamide yields ethanoic acid and
amine. The vapor was tested with moist red
litmus paper that turned blue because of the
basicity of the amine.
RCONH2 + NaOH => RCOO-Na+ + NH3
In alcoholysis, acetyl chloride and acetic
anhydride formed ester that was distinguished
by its smell upon its reaction with ethanol and
H2SO4.

3.) Aminolysis: Anilide Formation

Several drops of acetyl chloride and
acetic anhydride was mixed with 0.5mL of
aniline. This was later transferred to another test
tube that contained 5mL of water. Precipitation
was recorded.

In aminolysis, an oily layer was formed

as a result of the difference in density and
solubility of the compounds in the test tube.
Anilide was also present as a white precipitate
that yielded upon the addition of water.

In hydroxamic acid test, yellow

coloration of resulting mixture in preliminary
test showed the enolic property of the mixture.
Upon heating with NH2OH.Cl, acetamide and
ethyl acetate were converted into hydroxamic
acid. Deep burgundy discoloration of the ethyl
acetate and acetamide was seen from reaction of
FeCl3 and hydroxamic acid.

Brown, William H. (1997). Introduction to

Organic Chemistry. USA: Saunders College
Publishing.
Bayquen A. V., Cruz C.T., de Guia R. M. et al.
2009. Laboratory Manual in Organic Chemistry.
C&E Publishing, Inc., Quezon City, Philippines

To conclude, this experiment goes to

show that carboxylic acid and its derivatives
could be classified or identified by the means of
various classification tests. That each derivative
would have a unique property to distinguish one
from another. Types of nucleophilic acyl
substitution that carboxylic acids and its
derivatives go through the following:
hydrolysis, aminolysis, and alcoholysis. By
having a positive result, a certain carboxylic
acid derivative could be identified.

Carboxylic
Acids
and
Derivatives.
http://www.rapidlearningcenter.com/chemistry/o
rganic_chemistry/carboxylic-acids-andderivatives.html 10/02/10

REFERENCES

Jml/crbacid2.htm

McMurry, John (2010). Foundations of Organic

Chemistry. Philippine ed. Philippines: Cengage
Learning Asia Pte. Ltd.
Carboxylic Acid Derivatives Reactivity
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxt