Experiment 8

COMPARATIVE REACTIONS OF CARBOXYLIC ACID DERIVATIVES
Gwyneth Ysabelle M. Guevarra, Antonio Miguel F. Jorge, Patricia Izakhie Labiano,

Jan Abbygale T. Lacsamana, and Regine Coeli M. Lansangan
Group 3 1G Medical Technology Inorganic and Organic Chemistry Laborataory
ABSTRACT
An organic compound containing at least one carboxyl group is classified as a carboxylic acid. It has a general formula
of R-COOH and can form various derivatives that are characterized by an electronegative atom attached to the carbonyl
carbon. Carboxylic acid derivative typically undergoes nucleophilic acyl substitution reaction to take place. This
experiment aims to determine the characteristic reactions of carboxylic acid and its derivatives under hydrolysis,
aminolysis, alcoholysis, and hydroxamic test.
INTRODUCTION
Carboxylic acid, a class of organic compound,
contains a carboxyl group. The functional group of
this organic acid is comprised of a carbon atom
that is double bonded to an oxygen and to a
hydroxyl group by a single bond. The replacement
of the hydroxyl group from a carboxyl group With these being said, this comparative
produces the derivatives of carboxylic acid experiment aimed to differentiate reactivity of
(Bettelheim, Brown, Campbell, Farrell, & Torres, carboxylic acid derivatives using different chemical
2012). reactions. Another objective of this experiment
was to establish better understanding on
nucleophilic acyl substitution that occurs in
halides, anhydrides, esters, and amides.
Figure 1. Formula Representation of Carboxylic
Acid Derivatives
EXPERIMENTAL
According to Kennepohl, Farmer & Soderberg I. Samples and Reagents
(2019), carboxylic acid derivatives are functional The main organic compounds used in the
groups that was generated through nucleophilic experiment were presented on Table 1.
acyl substitution. Acylation reaction generally
takes place by an addition-elimination process Table 1. The Molecular Formula and Condensed
where in a nucleophile attacks on an electrophilic, Structure of the Prescribed Analytes
a slightly positive atom, carbonyl carbon due to its
resonance effects to form a tetrahedral
intermediate (Reusch, 2013). The reaction of a ANALYTE MOLECULAR CONDENSED
tetrahedral intermediate is manifested by the FORMULA STRUCTURE
replacement of a leaving group, an acyl group, by Acetyl CH3COCl
the nucleophile, which will then become the new Chloride
acyl group. Therefore, nucleophilic acyl Acetic C4H6O3
substitution occurs when one acyl group is Anhydride
substituted with another acyl group forming a new Ethyl Acetate C4H8O2
carboxylic acid derivative (Kennepohl et al., Benzamide C7H7NO
2019).
FIGURE 2. The General Structural Formula of

Each Carboxylic Acid Derivatives
The odor of the ester formed was noted through
wafting motion.
III. Aminolysis: Anilide Formation with a

Primary Amine
A mixture of 0.5 mL aniline and 0.5 mL of
acetyl chloride was prepared in a test tube. In
another test tube, the same amount of aniline
was treated with 0.5 mL of acetic anhydride.
Both test tubes were covered with parafilm so
that the components can be mixed well.
Afterwards, 0.5 mL of cold water was added in
each test tubes.
IV. Hydroaxamic Acid Test for Carboxylic Acid
Derivatives
In a test tube, 2 drops of the carboxylic acid
derivative sample were placed, where in 2 mL
of alcoholic NH2OH*HCl and 1 M KOH was also
added. The test tube was placed in a boiling
water bath for about 2 minutes. Consequently,
A. Procedure the mixture was cooled to room temperature
I. Hydrolysis then 1 mL of 5% FeCl3 was added.
a. Carboxylic Acid Halides & Anhydrides
In two different test tubes, 20 drops of water
were placed in each. Five drops of acetyl chloride REFERENCES
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COMPARATIVE REACTIONS OF CARBOXYLIC ACID DERIVATIVES

Gwyneth Ysabelle M. Guevarra, Antonio Miguel F. Jorge, Patricia Izakhie Labiano,

FIGURE 2. The General Structural Formula of

III. Aminolysis: Anilide Formation with a

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