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Form 1A: Laboratory Formal Report Title Page

CHEM 101 Lab: ORGANIC CHEMISTY
1stSemester, AY 2020-2021
Sevetrim B. Torrejos
Professor
TESTS FOR CARBOXYLIC ACIDS

By: DEMELINO, JUSTINE MAE T.

BS Food Technology Student
Date Started: Dec. 26, 2020 Date Finished: January 14, 2021
Deadline: January 15, 2021
I certify that this report is truly my own work: Signature: ______________
To be filled by instructor:

RATING BOX: PENALTY/X BOX:

Objectives (10%) Deadline:
Materials and Methods (10%) Date Received:
Introduction (10%) Time Received:
Results (20%) No. Of Days Late:
Discussion (20%) Late Penalty:
Answer to questions (20%) Punctuality Penalty:
Conclusion/ References (10%) UNKNOWN
Total (R)= Percent Error:
NET RATING= Rating (X):
[(70% R +30% X)-Late Penalty]
I. Introduction

A carboxyl group (COOH) is a functional group consisting of a

carbonyl group (C=O) with a hydroxyl group (O-H) attached to the same carbon
atom. Carboxyl groups have the formula -C(=O)OH, usually written as -COOH or
CO2H. Carboxylic acids are a class of molecules which are characterized by the
presence of one carboxyl group. As proton donors, carboxylic acids are
characterized as Bronsted-Lowry acids. Acids with two or more carboxylic groups
are called dicarboxylic, tricarboxylic, etc. Salts and esters of carboxylic acids are
called carboxylates. Carboxylate ions are resonance-stabilized. This increased
stability leads to increased acidity compared to that of alcohols. Generally, in
IUPAC nomenclature, carboxylic acids have an “-oic acid” suffix, although “-ic
acid” is the suffix most commonly used.Carboxylic acids are used as precursors
to form other compounds such as esters, aldehydes, and ketones. Carboxylic
acids can exhibit hydrogen bonding with themselves, especially in non-polar
solvents; this leads to increased stabilization of the compounds and elevates
their boiling points. Since they contain both hydroxyl and carbonyl functional
groups, carboxylic acids participate in hydrogen bonding as both hydrogen
acceptors and hydrogen donors.

A Carboxylic Acid is an organic compound containing a carboxyl

functional group. They occur widely in nature and are also synthetically
manufactured by humans. Upon deprotonation, carboxylic acids yield a
carboxylate anion with the general formula R-COO–, which can form a variety of
useful salts such as soaps. The carboxylic acids are the most important
functional group that present C=O. This type of organic compounds can be
obtained by different routes, some carboxylic acids, such as citric acid, lactic acid
or fumaric acid are produced from by fermentation most of these type of
carboxylic acids are applied in the food industry.

The general formula of a carboxylic acid is R-COOH, were COOH

refers to the carboxyl group, and R refers to the rest of the molecule to which this
group is attached. In this carboxyl group, there exists a carbon which shares a
double bond with an oxygen atom and a single bond with a hydroxyl group.

Carboxylic acids are characterized by the strong absorption due to

the carbonyl group in the infrared spectra of these compounds. The absorption
occurs in the same region as the carbonyl groups of aldehydes and ketones, but
the absorption for carboxylic acids occurs at slightly higher wavenumber, and
tends to be somewhat broadened. The O—H bond of carboxylic acids absorbs in
the same region as that for alcohols. However, the absorption is very much
broader for carboxylic acids, and it overlaps the C—H absorptions.
 Carboxylic acid contains a hydroxyl group attached to a carbonyl
carbon. Due to the electronegativity of the oxygen atom, this functional group can
undergo ionization and discharge a proton.

The carboxylate ion, produced from the removal of a proton from

the carboxyl group, is stabilized by the presence of two oxygen atoms (through
which the negative charge can move). Some common examples of carboxylic
acids include acetic acid (a component of vinegar) and Formic acid.

Generally, these organic compounds are referred to by their trivial

names, which contain the suffix “-ic acid”. An example of a trivial name for a
carboxylic acid is acetic acid (CH3COOH). In the IUPAC nomenclature of these
compounds, the suffix “-oic acid” is assigned.

Most of the properties of carboxylic acids are a result of the

presence of the carboxyl group. Some physical and chemical properties of these
compounds are discussed in this subsection.

Carboxylic acid molecules are polar due to the presence of two

electronegative oxygen atoms. They also participate in hydrogen bonding due to
the presence of the carbonyl group (C=O) and the hydroxyl group. When placed
in nonpolar solvents, these compounds form dimers via hydrogen bonding
between the hydroxyl group of one carboxylic acid and the carbonyl group of the
other. The solubility of compounds containing the carboxyl functional group in
water depends on the size of the compound. The smaller the compound (the
shorter the R group), the higher the solubility. The boiling point of a carboxylic
acid is generally higher than that of water. These compounds have the ability to
donate protons and are therefore Bronsted-Lowry acids. They generally have a
strong sour smell. However, their esters have pleasant odours and are therefore
used in perfumes.

The α-carbon belonging to a carboxylic acid can easily be

halogenated via the Hell-Volhard-Zelinsky reaction. These compounds can be
converted into amines using the Schmidt reaction. A carboxylic acid can be
reduced to an alcohol by treating it with hydrogen to cause a hydrogenation
reaction. Upon reaction with alcohols, these compounds yield esters.

In this activity, there are four tests used to test carboxylic acid.
These tests used are litmus test, sodium bicarbonate test, Ester test, and
Fluorescein test (for Dicarboxylic acid).

II. Objectives

At the end of the experiment, the student would be able to:

 1. Understand what is carboxylic acid.
2. Know and understand the tests for carboxylic acid.
3. Identify the differences between results of different tests.
4. Know the importance and applications of carboxylic acids in different
fields.

III. Materials

(a.) Litmus test

 Blue litmus paper

 Dropper
 Carboxylic acid

(b.) Sodium bicarbonate test

 Test tube
 Beaker
 Saturated sodium bicarbonate solution

(c.) Ester test

 Test tube
 Beaker
 Water bath
 Dropper
 Concentrated sulfuric acid

(d.) Fluorescein test (Dicarboxylic acid)

 100mg phthalic acid

 200 mg resorcinol
 3 drops of conc. sulfuric acid
 100 mL 5M NaOH
 Dry test tube
 Beaker
 Dropper
 Bunsen burner

IV. Procedures
(a.) Litmus test

1. Prepare dropper, carboxylic acid, and a blue litmus paper.

2. Few drops of carboxylic acid was dropped in the blue litmus paper.

(b.) Sodium bicarbonate test

1. 2mL of saturated sodium bicarbonate solution was taken to the test tube.
2. Into that, few mL of carboxylic acid from the beaker was added.

(c.) Ester test

1. Clean and dry test tube was taken.

2. Into that, 1mL of carboxylic acid was added to a dry test tube.
3. 1mL of ethyl alcohol was added to the carboxylic acid in the test tube.
4. Compounds were mixed well by shaking.
5. 3-4 drops of concentrated sulfuric acid was added into the test, then mixed
well.
6. The test tube was then placed in a hot water bath for few minutes.
7. The contents of the test tube was then poured into a 30mL of distilled
water and mixed well.

(d.) Fluorescein test ( Dicarboxylic acid )

1. Clean and dry test tube was taken.

2. 100mg of phtalic acid was added in the test tube.
3. 200mg of resorcinol was then added. (The amount of resorcinol should
roughly double the amount of phthalic acid.)
4. It was then shaked well in order to mix the contents evenly.
5. 3 drops of conc. sulfuric acid was added to the contents.
6. The contents of the test tube was gently heated over the bunsen burner
flame.
7. Small volume of 5M of NaOH was added and poured into the content in
the test tube and then poured again into the beaker with the remaining 5M
NaOH solution.
8. It was then tested if the solution was alkaline or not by dipping a red litmus
paper.
9. And to test the presence of fluorescein, normal white light was passed
through it.
10. In the presence of UV light, fluorescein was added into the distilled water
under UV light.

V. Results and Discussions

 Carboxylic acids have a tendency to donate protons and act as
acids. It is this property which is helpful in the identification of a -COOH group.
Any of the following test can be carried out to detect the carboxylic functional
group; Litmus test, Sodium bicarbonate test, Ester test, and Fluorescein test
which is for Dicarboxylic acid.

Test for carboxylic acid Result

Litmus test Carboxylic group turns blue litmus red.

Table 1. Results after litmus test was made.

Table 1 shows the result of the litmus test made with the carboxylic
acid. After dropping the carboxylic acid into the blue litmus paper, it turns red.
This result in figure 1 indicates the presence of carboxylic acid. The carboxylic
acid turns blue litmus red. Because the hydroxyl group present in -COOH is far
acidic than in alcohol.

Test for carboxylic acid Result

Sodium bicarbonate test Brisk effervescence indicates the

presence of carboxylic acid

Table 2. Results after sodium bicarbonate test was made.

 Table 2 shows the observations and results after the sodium
bicarbonate test was made with tge carboxylic acid. After shaking, evolution of
brisk effervescence was observed as shown in figure 2. This indicates that
carboxylic acid is present. The evolution of carbon dioxide during the reaction
causes brisk effervescence in sodium bicarbonate test.

Test for carboxylic acid Result

Ester test Formation of a fruity and sweet smelling

compound indicates the presence of
carboxylic group.

Table 3. Results after ester test was made.

Table 3 shows the observations made after the ester test was made.
Formation of a sweet smelling compound and a fruity small as well indicates the
presence of carboxylic group. An ester is an organic compound that is a derivative of a
carboxylic acid in which the hydrogen atom of the hydroxyl group has been replaced
with an alkyl group. Because the reactions are slow and reversible, there's less esters
produced. The smell is often masked or distorted by the smell of the carboxylic acid. A
simple way of detecting the smell of the ester is to pour the mixture into some water in
a small beaker as shown in figure 3. As the esters get bigger, the smells tend towards
artificial fruit flavouring - "pear drops", for example.

Test for diarboxylic acid Result

Fluorescein test Appearance of green colour fluorescent

solution indicates the presence of acid group.

Table 4. Results after Fluorescein test was made.

Table 4 shows the results obtained after Fluorescein test was made with
the carboxylic acid. Presence of dicarboxylic acid shows the appearance of green colour
fluorescent solution. Fluorescein emits an intense green fluorescence in the presence of
alkaline solutions like dicarboxylic acid.

VI. Conclusions

Carboxylic acids are organic compounds containing carboxyl functional

group. It is of two types aliphatic and aromatic. Aliphatic acids are soluble in water
where as aromatic acids are sparingly soluble in water. Formic acid and acetic acid are
the simplest aliphatic acid and benzoic acid is the simplest aromatic acid. Formic acid
and acetic acid are liquids. Carboxylic acids such as benzoic acid, oxalic acid, phthalic
acid, tartaric acid etc are colourless crystalline solids.

Carboxylic acids are widespread in nature, often combined with other

functional groups. Simple alkyl carboxylic acids, composed of four to ten carbon atoms,
are liquids or low melting solids having very unpleasant odors. The fatty acids are
important components of the biomolecules known as lipids, especially fats and oils. As
shown in the following table, these long-chain carboxylic acids are usually referred to by
their common names, which in most cases reflect their sources. A mnemonic phrase for
the C10 to C20 natural fatty acids capric, lauric, myristic, palmitic, stearic and arachidic
is: "Curly, Larry & Moe Perform Silly Antics" (note that the names of the three stooges
are in alphabetical order).

Interestingly, the molecules of most natural fatty acids have an even

number of carbon atoms. Analogous compounds composed of odd numbers of carbon
atoms are perfectly stable and have been made synthetically. Since nature makes these
long-chain acids by linking together acetate units, it is not surprising that the carbon
atoms composing the natural products are multiples of two. The double bonds in the
unsaturated compounds listed on the right are all cis (or Z).

The form in which acids are present in the analyzed material is

important to the analyst: whether they are free, in aqueous solution, in the form of
salts or solutions of these salts, or mixed with other neutral or acid substances.
The character of the sample determines the course of the analytical procedure. It
is also important to bear in mind that some carboxylic acids are volatile (lower
aliphatic monocarboxylic acids), some are volatilized by steam distillation
(monocarboxylic acids), others are water soluble (lower monocarboxylic and
certain dicarboxylic acids), and practically all are soluble in 5% sodium hydrogen
carbonate. All these properties offer a possibility of separating these substances
from others. As carboxylic acids do not give char-acteristic color reactions, all
general detections of this class of substance are based on their acidity. This is
determined in aqueous solutions by means of indicators, and in the case of
water-insoluble acids on the basis of their solubility in 5% sodium hydrogen
carbonate. In all instances, however, it is advisable to complete the proof of
acidity by titration with alkali; in the case of pure acids by determining their NE
(neutralization equivalent), which is characteristic for each acid.

With the help of various tests, presence of carboxylic acid can be

identified. Carboxylic acid turns blue litmus red. The hydroxyl group in carboxylic is
far more acidic than that in alcohol. Carboxylic acids reacts with sodium hydrogen
carbonate to produce carbon dioxide gas which can be seen in the form of a
brisk effervescence.Carboxylic acid reacts with alcohol in presence of conc.
sulphuric acid to form ester that is identified by the presence of a fruity smell.
Also, green fluorescent is obtained due to the presence of alkaline solution

Carboxylic acids have many uses and applications in different fields

which really contribute to a great advantage for all of us. Fatty acids that are
essential to human beings are made up of carboxylic acids. Examples include
omega-6 and omega-3 fatty acids. Higher fatty acids are also used in the
manufacture of soaps. The production of soft drinks and many other food
products involve the use of many carboxylic acids. The manufacture of rubber
involves the use of acetic acid as a coagulant. Hexanedioic acid is used in the
manufacture of nylon-6,6. Carboxylic acids have numerous applications in the
rubber, textile, and leather industries. Ethylenediaminetetraacetic acid is a widely
used chelating agent. The synthesis of many drugs involves the use of these
compounds. Therefore, carboxylic acids are very important in pharmaceuticals.
The production of many polymers involves the use of compounds containing the
carboxyl functional group.

VII. References

https://youtu.be/s-O7UpF_Fe0 (Tests for Caboxylic acid)

esterification - alcohols and carboxylic acids. (n.d.). Esterification. Retrieved January 14,
2021, from
https://www.chemguide.co.uk/organicprops/acids/esterification.html

Mott, V. (n.d.). Carboxylic Acids | Introduction to Chemistry. Carboxylic Acid. Retrieved

January 14, 2021, from
https://courses.lumenlearning.com/introchem/chapter/carboxylic-acids/

Libretexts. (2020a, August 11). 9.8: Carboxylic Acids and Esters. Chemistry LibreTexts.
https://chem.libretexts.org/Courses/Sacramento_City_College/SCC
%3A_CHEM_330_-_Adventures_in_Chemistry_(Alviar-
Agnew)/09%3A_Organic_Chemistry/9.08%3A_Carboxylic_Acids_and_Esters