THE DIFFERENTIATION OF CARBOXYLIC ACID AND THEIR DERIVATIVES USING

CLASSIFICATION TESTS
Kim Genesis DR. Tuazon, Carl Ubana, Anjelica Versoza,
Karen Faith Villaflores, Jeremiah Jan M. Vivar
Group 8
2D Pharmacy
Organic Chemistry Laboratory
ABSTRACT
The experiment tested compounds to differentiate reactivity of carboxylic acids and distinguish carboxylic acid using
classification tests. The four tests were as follows, Hydrolysis of Acid Derivatives using acyl halides and acid
anhydrides, esters and amides this test was to know if the sample has undergone hydrolysis by comparing
temperatures, precipitates and the evolution of gas; Alcoholysis or the Schotten-Baumann Reaction using acetic acid
and acyl halides and acid anhydrides for testing this test was to know if the sample has undergone hydrolysis with the
compounds given, odor and formation of layers were compared; Aminolysis or the Anilide formation was the third
test, it used acyl halides and acid anhydrides to observe if it has undergone aminolysis we observed a white
precipitate; Hydroxamic Acid Test using Ethyl acetate and acetamide, observed in this test was a yellow solution for
the preliminary test and a deep burgundy in the addition of 5% FeCL

INTRODUCTION

EXPERIMENTAL

Carboxylic acids and their derivatives are

organic compounds containing the acyl
group core structure attached to a Y group,
which may be an electronegative atom or a
substituent. This experiment aims to
Differentiate the reactivities of carboxylic
acids and to distinguish carboxylic acids
using classification tests. [1] Carboxylic
acids are organic compounds that have a
carboxyl group attached to an aryl group
(ArCOOH). The R may be a hydrogen and
the result is formic acid. They may be mono
carboxylated,
multi
carboxylated,
substituted (hydroxyl groups) or they may
be
aromatic.
Physical
properties
of
carboxylic acids are as follows; Low
molecular weight carboxylic acids are
soluble in water and therefore lie in class S1.
Water insoluble acids dissolve in both
sodium hydroxide solution and sodium
bicarbonate solution, being classified as
under class A1. When they react with
sodium bicarbonate, they evolve carbon
dioxide gas. This is considered as a good
simple indication of them. The reactions of
carboxylic acid in chemical means is related
to: the proton as in salt formation reactions,
removal of the hydroxyl group as in
conversion to derivatives such as esters,
amides or acid chlorides, substitution either
in the alpha position of aliphatic acids or in
the meta position of aromatic ones.

A. Compounds Tested: Acetyl chloride,

Acetyl anhydride, Ethyl acetate, Benzamide,
Acetic acid, Acetamide.
Structural formula of the compounds used:
1. Acetyl Chloride

2. Acetyl Anhydride

3. Ethyl Acetate

4. Benzamide

5. Acetic Acid

6. Acetamide

B. Procedure
1. Hydrolysis of acid derivatives
a. Acyl halides and Acid Anhydrides
1 ml of water was placed in a test tube.
10 drops of acetyl chloride/acetic anhydride
were added to the test tube with 1 ml
water. The resulting mixture was divided in
to two portions. In the first portion, 1 ml of
2%AgNO3was added. In the second portion,
1 ml of saturated NaHCO3 was added.
b. Esters
2 ml of 25% NaOH solution was added to
1ml of Ethyl acetate. the mouth of the test
tube was covered with a marble and then
subjected to a boiling water bath for
5minutes. The sample was neutralized with
10% HCl solution
c. Amides
1ml of benzamide was treated with 5ml
of 10% NaOH solution and was heated to
boiling. Litmus paper was then held against
the mouth of the test tube
2. Alcoholysis: Schotten Baumann
Reaction
A mixture of 10 drops of acetic acid, 1 ml
ethanol and 5 drops of conc. H2SO4 was
heated till warm and subjected to a water
bath for 2 minutes. 0.5 ml of ethanol, 1ml of
water and0.2ml of acyl halide or acid
anhydride sample are put in another test

tube. In the mixture was added 2ml 20%

NaOH solution. A cork or parafilm were used
as stopper for the test tube and was shaken
for several minutes.
3. Aminolysis: Anilide Formation
A few drops of acetyl chloride or acetic
anhydride sample were added to
0.5mlaniline and was transferred to a new
test tube containing 5ml water.
4. Hydroxamic Acid Test
Preliminary test: 2 drops of the sample
were mixed with1ml of 95% ethanol and 1M
HCl. 1drop of 5% FeCl3 was added to the
solution. It is noted that if another color
other than yellow is obtained, the test
would not be used. Otherwise, the test is
conducted as follows: 2 drops of the sample
were added to 2ml of alcoholic NH2OHHCl
and ml of 1M KOH. The solution was heated
in a boiling water bath for 2 minutes. After
which it was cooled and then 1ml of 5%
FeCl3 was added.

RESULTS AND DISCUSSION

Table 1. Hydrolysis of Acid Derivatives
Observations
Acyl halides
and Acid
Anhydrides
Acetyl
Chloride
Acetic
Anhydride
Ester: Ethyl
Acetate
Amide

Warming
effect

Upon
addition
of 2%
AgNO3

Warming
Whit ppt,
effect
AgCl3
No
No ppt
warming
effect
Odor: Vinegar like

Upon
addion of
saturated
NaHCO3
Evolution of
Gas, CO2
Evolution of
Gas, CO2

Red to Blue litmus paper

The acid halides and anhydrides acetyl

alcohol and acetic anhydride both showed
evolution of CO2 when NaHCO3 was added.
Upon addition of water andAgNO3, Acetyl
chloride showed warming effect and a white
cloudy precipitate, respectively; however
acetic anhydride did not show both warming
and precipitate. The Ester, Ethyl acetate,
after neutralizing with10% HCL and water
bathing, expressed a Fruity/Plastic-balloon
like odor The Amide, Benzamide, upon

heating turned basic, indicating presence of

ammonia with amine like odor.

Table4. Hydroxamic acid test

Observations
Preliminary test
Ethyl acetate
Acetamide

Figure1. Equations for Hydrolysis of Acid

Derivatives
Table2. Alcoholysis: Schotten- Baumann
Reaction
Acetic acid
Acyl halides and
acid anyhydrides
Acetyl chloride
Acetic anhydride

Observations
Odor: Plastic-balloon like odor
Odor
Formation of
layers
Plastic balloon
No layer formed
like
Fruity odor
No layer formed

The carboxylic acid, acetic acid, upon water

bathing for 2 minutes exhibited plastic
balloon like odor, but no layer was formed
Acyl halide, Acetyl chloride after addition of
20% NaOH solution and agitation, exhibited
also aplastic balloon like odor and formation
of no layers.

Figure2. Representation of Alcoholysis

Table3. Aminolysis: Anilide Formation

Observations
Acyl halides and acid
Appearance of precipitate
anhydrides
Acetyl chloride
White precipitate
Acetic anhydride
White precipitate

Acetyl Chloride and Acetic Anhydride

exhibited formation of white precipitate
upon addition of 0.5ml aniline.

Yellow solution
Yellow solution

Upon addition of
5% FeCl3
Deep burgundy
Deep burgundy

A Preliminary test was done to eliminate

those phenols that give color with ferric
chloride in acidic solution that would
therefore give false positive result in the
ferric hydroxamic test. Ethyl acetate ande
Acetamide yield deep burgundy color which
was a positive result.
REFERENCES:
[1] Jaism, A., Mohammad, D. (2012) A
Laboratory manual on practical organic
chemistry for second year students.
University of Baghdad.
Pavia, D., Lampman, G., Kriz, G., & Engel, R.
(1998).
Introduction to organic
laboratory techniques: a microscale
approach.3rd Ed. USA: Saunders Publishing
Comapany.
Williamson, K; Minard, R; Masters K. (2007).
Macroscale and microscale organic
experiments. 5th Ed. Boston, USA: Houghton
Mifflin Company.
Garner, CM. (1997). Techniques &
experiments for advanced organic
laboratory. USA: John Wiley & Sons. Inc.
MACAULAY, DB. (2007). General, organic &
biological chemistry an integrated approach.
USA: John Wiley & Sons. Inc.