CLASSIFICATION TESTS FOR CARBOXYLIC ACIDS AND THER DERIVATIVES

Ma. Patricia Anne S. Operaa, Jezreel Nikholai M. Paras, Maria Rizza Kristina P. Perey,
Ma. Carla R. Pulgar, Vanessa Lyn G. Ramos, Jessica Mae G. Renti Cruz
Group 5 2E Pharmacy
UST, Faculty of Pharmacy

ABSTRACT
The process of recrystallization involves dissolution of the solid organic compound in an appropriate
solvent at an elevated temperature then cooled. In this experiment, acetanilide, the crude product of acetic
anhydride and aniline, was used as the organic compound. For the recrystallizing solvent, water was
determined to be the appropriate solvent due to the fact that acetanilide was able to dissolve in a warm
bath unlike ethanol and hexane. Crude acetanilide and water underwent recrystallization by heating the
mixture in a water bath and was cooled in an ice bath. The melting point was also obtained through an oil
bath which is 112-115C. The percentage recovery in the experiment was 24. 51%.

I.

INTRODUCTION
Carboxylic acid derivatives are
compounds in which the -OH of the
carboxyl group is replaced by certain
other groups. (Brown) Examples are the
carboxylic
acid,
amides,
esters,
thioesters acyl halide, and acid
anhydrides. They are a family of closely
related functional groups that undergo
nucleophilic acyl substitution. As stated
in the website chem.ucalgary.ca, they
share a common reactivity pathway with
nucleophiles. The most common among
the carboxylic acid derivatives are acid
anhydrides, acyl halides, esters and
amides.
Based on the carboxylic acid
derivatives reactivity, among them,
carboxylate groups are the least
reactive towards nucleophilic acyl
substitution, next are amides, then
esters and carboxylic acids, thioesters,
and last are the acyl phosphates, which
are the most reactive among the
biologically relevant acyl groups.
(Soderberg)

Reactions like hydrolysis of acid

derivatives, alcoholysis: Schotten-

Baumann, and aminolyis: anilide

formation
are
involved
in
the
experiment. Hydroxanamic acid test was
also used in the experiment. In the
hydrolysis of acid derivatives, all acid
derivatives can be hydrolyzed to yield
carboxylic acids: the condition range
from mild to severe depending on the
compound involved. (Brown) Based on
the website name-reaction.com, an
organic reaction used to convert an acyl
halide or anhydride to an amide if
reacted with an amine base, or an ester
if reacted with an alcohol and base is
called the Schotten-Baumann Reaction.
Another reaction in the experiment is the
aminolysis or the anilide formation.
This
experiment
aims
to
differentiate the reactivities of carboxylic
acids and their derivatives. It also aims
to distinguish carboxylic acids and their
derivatives using some classification
tests.

II. MATERIALS AND METHOD

Samples Used:
Acetyl chloride
Acetic anhydride
Ethyl acetate
Aceta mide
Benzamide
A. Hydrolysis of Acid Derivatives
Use acetyl chloride and acetic
anhydride as samples. Place 1 mL of
water in a test tube then add 10 drops of
the sample dropwise. Note for a
warming effect. Divide the mixture into
two portions. To the first half, add 1 mL
of 2% AgNO3. Identify its miscibility. To
the second half, add 1 mL of saturated
NaHCO3. Note for the evolution of gas.
Use ethyl acetate as sample. Add
2 mL of 25% NaOH solution to the 1 mL
of sample. Then, cover the mouth of the
test tube with a marble and heat in a
water bath for 5 minutes. Lastly, add
10% HCl solution to neutralize. Take
note of odor.
Use benzamide as sample. Add 5
mL of 10% NaOH solution to the 1 mL
sample then heat to boiling. During
heating, test the reaction of gas evolved
by placing a moist red litmus paper on
the test tube. Note the change of color
to the litmus paper.
B. Alcoholysis: Schotten-Baumann
Reaction
Use acetic acid as sample. Add 10
drops of sample, 1 mL of alcohol, and 5

drops of concentrated H2SO4 in a test

tube the heat in a water bath for 2
minutes.
Use acetyl chloride and acid
anhydride as sample. Place 0.5 mL of
alcohol, 1 mL of water, 2 mL of 20%
NaOH and 0.2 mL of sample. Cover the
test tube with parafilm then shake
vigorously. Note for odor and layers
formed.
C. Aminolysis: Anilide Formation
Add a few drops of acetyl chloride
or acetic anhydride to 0.5 mL aniline.
Transfer the mixture in a new test tube
containing 5 mL of water.
D. Hydroxamic Acid Test
Use the samples ethyl acetate and
acetamide. Preliminary Test: mix 2
drops of sample, 1 mL of 95% ethanol,
and 1 M KOH. Add 1 drop of 5% FeCl. If
the solution did not turn to yellow,
disregard the following steps.
Add 2 drops of sample to 2 mL of
NH2OHHCl and 1 mL of 1 M KOH the
heat in a water bath for 2 minutes. Cool
mixture then add 1 mL of 5% FeCl 3.
Take note of the color of the solution.
III. RESULTS AND DISCUSSION

IV.CONCLUSION
REFERENCES