CLASSIFICATION TESTS FOR CARBOXYLIC ACID AND DERIVATIVES

ABSTRACT

Carboxylic acids are organic compounds primarily characterized by the occurrence and presence of at least one
carboxyl group. The principal feature of carboxylic acid is its acidity, as it is generally more acidic than any other
organic compounds containing hydroxyl groups but it is weaker in a different sense. Carboxylic acid derivatives, on the
other hand, are organic compounds that are indicated by the incidence of a carbonyl group with an electronegative
atom attached to the carbon. On this experiment, one of the chief goals is to distinguish and discern the differences
between carboxylic acid derivatives through the classification tests. The classification tests performed and executed by
the group include the hydrolysis of acid derivatives, alcoholysis, aminolysis and hydroxamic acid test. These tests
yielded results which helped the group to infer in which of the following compounds are carboxylic acid and its
derivatives are present. In hydrolysis, both acetyl chloride and acetic anhydride reacted with evolution of gas but only
acetyl chloride was observed to have a warming effect with formation of precipitate. Benzamide on the other hand
proved to be basic. In alcoholysis, odors of the compounds were their distinguishing characteristics, plastic balloon-
like odor for acetic acid and fruity odor for acetyl chloride. Meanwhile, in aminolysis, formation of precipitate on both
compounds were clearly evident. In hydroxamic acid test, deep burgundy discoloration on the two compounds were
observed, excluding the preliminary test. Lastly, the reactions involved in each classification test were expounded
through the chemical equations and mechanisms and the reactivities of these compounds were singled out.

The objectives of the group include the aims to

differentiate the reactivities of carboxylic acid
INTRODUCTION derivatives, distinguish carboxylic acid derivatives
using classification tests and explain through
The important classes of organic compounds
chemical equations and mechanisms the
known as alcohols, phenols, ethers, amines and
reactions involved in each test.
halides consist of alkyl and/or aryl groups bonded
to hydroxyl, alkoxyl, amino and halo substituents
respectively. If these same functional groups are
Experimental
attached to an acyl group (RCO) their properties
are substantially changed, and they are
designated as carboxylic acid derivatives. A .Compounds tested
Carboxylic acids have a hydroxyl group bonded to
an acyl group, and their functional derivatives are The sample compounds tested for each
prepared by replacement of the hydroxyl group classification test include a.) acetyl chloride for
with substituents, such as halo, alkoxyl, amino hydrolysis, alcoholysis and aminolysis, b.) acetic
and acyloxy. (http://www2.chemistry.msu.edu/ anhydride for hydrolysis and aminolysis, c.) ethyl
faculty/reusch/virttxtjml/crbacid2.htm) acetate for hydrolysis and hydroxamic test, d.)
acetamide for hydroxamic acid test and lastly,
Carboxylic acid derivatives are group of organic e.) benzamide for hydrolysis.
compounds that contains a carbonyl group with
the presence of an electronegative atom, either
oxygen, nitrogen, or a halogen attached to the
carbonyl carbon. This difference in structure
leads to a major change in reactivity. The B. PROCEDURE
reactions of this group of organic compounds
typically involve substitution of the 1. PREPARATION AND ASSEMBLING OF
APPARATUSES
electronegative atom by a nucleophile. (http://
The instruments and apparatuses needed by
the group were prepared at firsthand, and these
include clean test tubes, beaker, parafilm, test
tube holder and rack and litmus paper. The
reagents necessary for each classification test
were also checked.
chemistry2.csudh.edu/rpendarvis/carboxder.htm)
 2. HYDROLYSIS of Acyl Halides & Acid derivatives
Anhydrides Acyl halides& Acyl
10 drops of the sample compounds namely Anhydrides
acetyl chloride and acetic anhydride were Acetyl chloride Warming effect,
separately introduced into a 1 ml of water in a
formation of white ppt.,
test tube. The resulting mixture of the two
compounds were divided into two portions and to evolution of gas
the first, drops of 2% AgNO3 were added and into Acetic anhydride No warming effect, no
the second portion, drops of saturated NaHCO3 ppt. Formed, evolution
were added. of gas
Esters
3. HYDROLYSIS of Esters Ethyl acetate Plastic balloon-like odor
1 ml of ethyl acetate was prepared into which 2 Amides
ml of 25% NaOH was added. The mouth of the Benzamide Evolution of gas, Red to
test tube was covered with parafilm and it was Blue litmus paper
heated for 5 mins. After heating, it was then change (BASIC)
neutralized by adding 10% HCl solution. Table 1. Results from Hydrolysis of Acid derivatives

4. HYDROLYSIS of Amides The warming effect observed in hydrolysis of acetyl

A few drops of benzamide was treated with 5
ml of NaOH solution and it was then heated. A
piece of moist red litmus paper was then placed
over the test tube to test the reaction of the gas
that evolved.
5. ALCOHOLYSIS
10 drops of acetic acid was mixed with 1ml of
ethanol and 5 drops of concentrated H2SO4 and
the mixture was then heated. Meanwhile, the
acetyl chloride sample was mixed with few drops
of ethanol, water and 20% NaOH solution. The
test tube was then covered with parafilm so it
could be shaked.
6. AMINOLYSIS
Few drops of aniline was added to separate test
tubes containing acetyl chloride and acetic
anhydride. 5 ml of water was then added to both
separate mixtures.
chloride was due to the exothermal reaction and
eventually the formation of the acetic acid, the
parent carboxylic acid.
25 % NaOH, which is an aqeous base, was used to
hydrolyze ethyl acetate which eventually yielded
acetic acid with alcohol and produced a plastic
balloon-like odor.
Benzamide yields ethanoic acid plus amine upon
heating in 5 mL of 10% NaOH solution. The
resulting vapor from the reaction upon testing with
moist litmus paper was basic duet o the basic nature
of amine.
Hydrolysis is the addition of water to form
f o r m carboxylic acids. The reaction is seen in
Figure 1:

7. HYDROXAMIC ACID TEST

Few drops of separate ethyl acetate and
acetamide was added with 2 ml of NH2OHHCl
and 1 ml of 1M KOH. The mixture was then
Figure 1. Reaction in Hydrolysis

Table 2 shows the results and observations

acquired from the alcoholysis test.
heated and cooled afterwards. 1 ml of 5% FeCl3
was finally added to the mixture. Alcoholysis Observations
Acetic acid Plastic balloon-like odor
RESULTS AND DISCUSSION Acetyl chloride Fruity odor
Table 2. Results of Alcoholysis
Table 1 shows the results and observations
acquired from the hydrolysis test. The agreeable odor of both mixtures was formed upon the
reaction of acetyl chloride and acetic acid with ethanol and
Hydrolysis of Acid Observations H2SO4.
 Alcoholysis is the reaction with an alcohol to yielded upon addition of water. In short,
yield amides. This is seen in the Schotten- aminolysis can be described as the reaction of
Baumann reaction, as shown in Figure 2, which amines to yield amides.
involves conversion of acid to acid chloride:

Table 4 shows the results and observations

acquired from the hydroxamic acid test.

Hydroxamic Acid Observations

Figure 2. Schotten-Baumann reaction in Test
Alcoholysis Ethyl acetate Deep burgundy
discoloration
Acetamide Deep burgundy
Table 3 shows the results and observations discoloration
acquired from the aminolysis test. Table 3. Results from Hydroxamic acid test

Aminolysis Observations
Acetyl chloride Formation of dark red
gel-like precipitate
Acetic anhydride Formation of dark red
The deep burgundy discoloration of the two
gel-like precipitate
Table 3. Results from Aminolysis compounds was brought about by the reaction of
hydroxamic acid with FeCl3.
The precipitate formed in aminolysis was due to
to the presence of anilide the mixture, which was

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[1] Bayquen, Aristea V., et al. (2009). Laboratory

Manual in Organic Chemistry. Manila: C&E
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[4] Carboxylic Acids

http://www2.chemistry.msu.edu/
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[5] Carboxylic Acids and Derivatives

http://chemistry2.csudh.edu/rpendarvis/carboxd
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