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Authors: *Constantino, Faye R., Dagcuta, Arnoika P., Brillo, Paulo D.C., Calicaran,
Diane Jean P., Calumay, Marie Cris C., Chan, Jannelyn P.
Abstract
Carboxylic acid is a functional group containing a carbonyl and hydroxyl group,
which is also known as carboxyl group. It has derivatives namely acyl halides, acid
anhydrides, amides, and esters. These are functional groups which are derived from the
carboxylic acid. This experiment aims to perform the different classification tests to the
sample compounds, differentiate carboxylic acids and their derivatives through the
tests, and identify the chemical reactions involved in the tests which are responsible for
the observed results. The experiment was divided into 4 tests: A. Hydrolysis of Acid
Derivatives, B. Alcoholysis: Schotten-Baumann Reaction, C. Aminolysis: Anilide
Formation, and D. Hydroxamic Acid Test and performed to the sample compounds. The
sample compounds were acetyl chloride, acetic anhydride, ethyl acetate, acetamide,
and benzamide. The reaction in the first three tests involves nucleophilic acyl
substitution wherein the nucleophile attached to a carbonyl group is replaced by
another nucleophile. In the hydrolysis of acyl halides and acid anhydrides, acetyl
chloride produced a warming effect, and formed a white precipitate upon addition of
2%AgNO3. Evolution of gas is present in both samples upon addition of saturated
NaHCO3. A vinegar-like odor is observed in ethyl acetate, and a change of red litmus
paper to blue is observed in hydrolysis of benzamide. In the alcoholysis of acetic acid, a
plastic-like odor evolved which is explained by the CH3COOCH2CH3 product. The
alcoholysis of acetic anhydride and acetyl chloride both produced ethyl ethanoate which
is expressed in the plastic balloon-like/ fruity odor. In the aminolysis of acetyl chloride
and acetic anhydride, both samples formed a yellow oily layer, but the result is must be
the formation of a white precipitate which indicates an anilide formation. In
hydroxamine acid test, both the acetamide and ethyl acetate gave yellow solution and
brown
precipitate.
I. Introduction
Carboxylic acid is a functional group
containing a carbonyl and hydroxyl
group, which is also known as carboxyl
group. Their presence in nature is
abundant and they are important
building block of foodstuffs such as
vinegar, butter and vegetable oils.
Acyl halides, acid anhydrides, esters,
and amides are functional groups
derived from the carboxyl group. Acyl
halides is an acyl group (RCO--) bonded
to a halogen atom. Acid anhydrides are
two acyl group bonded to an oxygen
Functional
Group
Acyl
Halides
IUPAC
Name
Acetyl
chloride
Acid
Acetic
Anhydrides anhydride
Structural
Formula
Esters
Ethyl
acetate
Amides
Benzamide
Esters:
Two milliliters of 25%NaOH solution
was added to one milliliter of ethyl
acetate. The test tube mouth was
covered with marble, and it was heated
in boiling water bath for five minutes.
The mixture was neutralized with
10%HCl solution, and with wafting
motion, the odor was noted.
Amides:
One milliliter of benzamide was
treated with five milliliters of 10%NaOH
solution, and it was heated to boiling.
During heating, the reaction of gas
evolved was tested by holding a piece of
moist red litmus paper over the test
tube. The change in the color of the
litmus paper is observed.
B. Alcoholysis:Schotten-Baumann
Reaction
Acetic Acid:
A mixture of 10 drops of acetic acid, 1
mL
ethanol,
and
5
drops
of
concentrated H2So4 was heated through
water bath. The odor of the ester
formed was noted.
Acyl Halides and Acid Anhydrides:
III. Results
Table 3: Hydrolysis Results
Hydrolysis of Acid
Derivatives
Acyl halides and Acid
anhydrides
Observations
1. Acetyl chloride
Acetic anhydride
Warming Effect
Upon addition
of 2% AgNO3
With warming
effect
Presence of a
white
precipitate
No precipitate
Upon addition
of saturated
NaHCO3
Evolution of
gas
No warming
effect
Odor: Vinegar-like odor
Litmus paper: Red to Blue
Evolution of
gas
Alcoholysis: SchottenObservations
Baumann Reaction
Acetic acid
Odor: plastic balloon-like
Acyl Halides and Acid
Odor
Formation of Layers
anhydrides
Acetyl chloride
Plastic balloon-like
None
Acetic anhydrides
Fruity
None
Table 5: Aminolysis Results
Observations
White precipitate
White precipitate
Observations
Preliminary Test
Upon addition of 5% FeCl3
Yellow
Yellow-orange w/ brown ppt
Yellow
Yellow-orange w/ brown ppt
IV.
Discussion
The
acetic
anhydride,
a
representative of acid anhydrides,
reacted with the alcohol and base in a
similar way as the acetyl chloride. The
resulting ester was still ethyl ethanoate
(C4H8O2).
The
reaction
was
References:
Carboxylic Acid and its Derivatives
McMurry
J.(2008).
Organic
th
Chemistry(7 ed.). CA: Brooks/Cole
(n.d.). Caboxylic Acid
Derivatives. Retrieved October 25,
2014
from
http://crab.rutgers.edu/~alroche/Ch
21.pdf
Roche
A.
Reactions
of
Derivatives
Carboxylic
Acid