CARBOCYCLE ACID COMPOUNDS

ABSTRACT

Experiments of carboxylic acids and esters have been conducted which aim to synthesize
esters and identify carboxylic acids and esters. The principle of this experiment is that the
production of esters is done by converting free fatty acids to methyl esters using an acid
catalyst and identifying carboxylic acid compounds and esters with several tests to observe
the color changes when reacted. In color identification several tests were carried out for
carboxylic acid tests, mono and poly carboxylic tests, deposition tests using FeCl3, KMnO4
test and AgNO3 and alkaline test, and the formation of esters. The results of this experiment
are that the carboxylic acid test produces a small amount of gas bubbles and a colorless
solution. At the formation of esters bubbles form and smell slightly ester. In the mono and
poly carboxylic test produces a green solution with black deposits. In the deposition test
using FeCl3 produces a solution that is yellow with white gelatin. In the KMnO4 test which
produces a clear concentrated purple solution (acetic acid), the concentrated purple solution
and there is gelatin (benzoic acid) and a solid black solution and there is gelatin (salicylic
acid). In the AgNO3 test and base which produces a colorless solution

Keywords: carboxylic acid, ester, esterification

PRELIMINARY un-ionized molecules. Dissociation

Carboxylic acid is an acid that has
a very important role. The carboxylic
function group, -COOH, is the
characteristic. When a hydroxyl group is
bonded directly to a carbon atom from a
carbonyl group, a new functional group will
be formed, namely the carboxyl group. The
compounds containing the carboxyl group
are acids, because in water these
compounds are slightly ionized by the
release of protons and can be neutralized
with bases. Carboxylic acids are viewed
structurally as aldehydes and ketones
because they contain carbonyl groups. The
difference is in acid because it contains a
carbonyl group. The difference is that in the
carboxylic acid there is a hydroxyl group
bound to carbonyl carbon. This causes a
specific nature, namely as acid. Carboxylic
acids are classified as weak acids because
they are only slightly ionized in water. At
equilibrium, most acids are in the form of
constant, Ka, carboxylic acid, where R as
an alkyl group, is 10-5 or less. Carboxylic
acids are compounds that are abundant in
nature (Wilbraham, 1992; Saurawati, 2006).
Most carboxylic acids have straight chains
which are initially separated from fat so that
they are also called weak acids. Propionic
acid is a three carbon acid, literally means
the first fatty acid (Greek: protos = first;
pawn = fat). Four carbon acids or butyric
acid are obtained from butterfat. Solubility
in water depends on the length and size of
the R group. Only acids with molecular
weight low (up to four carbons) that is very
soluble in water. Although included in weak
acids, carboxylic acids can react with bases
stronger than water. So even though
benzoic acid has a small solubility in water,
benzoic acid can react with sodium
hydroxide to form a soluble sodium
benzoate salt (Usman, 2013).
The reaction of an ester with water is called where the carboxylics will be reacted with
a hydrolysis reaction, namely the reaction ethanol, sulfuric acid, and sodium
produces carboxylic acid and alcohol. bicarbonate. The odor that comes out in the
Whereas the reaction of esters with a base solution indicates the formation of an ester.
is called a saponification reaction, The identification of a carboxylic acid and
producing alcohol and carboxylic salts. The ester compound is carried out by adding a
main difference between carboxylic acids few drops of sodium bicarbonate solution
and esters is the aroma. Carboxylic acids into a solution containing carboxylic acid
have an unpleasant aroma, but esters have a and ester, where this identification is
pleasant aroma. Esters can often be used as characterized by the appearance of gas.
flavouring agents, for example ethyl Identification of the physical properties and
butyrate esters which have a pineapple solubility of carboxylic and ester acids will
aroma (Hoydonckx, 2004). be carried out by deposition test using
Carboxylic acids have a low FeCl3, KmnO4 test, AgNO3 test and base.
molecular weight and have an odor at room
temperature, because carboxylic acids with
METHODOLOGY
molecular weight the height will be solid
Tools and materials
and form a very strong hydrogen bond with
The tools used in this experiment
low vapor pressure. So that only a few
are spray bottles, three feet, bunsen, drop
molecules are smelled by our nose. Esters
pipettes, volume pipettes, test tubes, and
do not form hydrogen bonds between
test tube racks,
molecules, esters are liquid at room
The materials used in this
temperature even though the molecular
experiment were aquades, acetic acid,
weight is high. So that the ester has a large
oxalic acid, sodium bicarbonate, benzoic
vapor pressure and many of its molecules
acid, carboxylic acid, salsilic acid,
are smelled by our nose and give it a scent
concentrated sulfuric acid, barium
(Respati, 1986).
hydroxide, ethanol, FeCl3, iron (II) sulfate,
Applications of carboxylic acids in
sodium hydroxide, KmnO4 and silver
the pharmaceutical industry are used in
nitrate.
drugs such as aspirin, phenacetin and
others. The food industry requires
Work procedures
carboxylic acid as a preservative and also as
Carboxylic acid Identification of
a coagulant in the manufacture of rubber.
carboxylic acid was carried out by inserting
The application of esters is as an essence
into the test tube a carboxylic acid (salicylic
for food and drinks, as an ingredient for
acid) compound of 5 etes, adding 5 drops of
making soap and for analgesic treatment
NaHCO3. It is necessary to remove the gas
(Sukmanawati, 2009). The purpose of this
from the test tube, and note the changes that
experiment is to know and understand the
occur.
reactions of carboxylic groups in a
compound and learn how to make esters
Esther formation
and identify carboxylic acid compounds
Formation of esters is carried out
and esters. The principle in the experiment
by inserting into a test tube as much as 1 ml
of carboxylic and ester acid compounds is
of carboxylic acid compound (salicylic
the production of esters by converting free
acid), plus 2 ml of ethanol and 5 drops of
fatty acids contained in triglycerides into a
concentrated sulfuric acid. Cooled and
methyl ester using sulfuric acid catalyst,
added NaHCO3, andobserved the smell
that comes out indicates the formation of RESULTS AND DISCUSSION
esters.
Observation data
Distinguish mono and poly carboxylates.
Identification to be able to distinguish Carboxylic Acid
mono and poly carboxylates was carried out
by entering oxalic acid and acetic acid into Treatment Observation
the reaction tube. Added 3 tets of 5 drops of
FeSO4 and NaOH solutions and observed Carboxylic-
the results obtained. containing
compounds are
Deposition test with FeCl3 inserted into the test
The deposition test with FeCl3 was tube 5 drops of
carried out by inserting 5 mg of benzoic salicylic acid
acid into the test tube and dissolving it with Added a few drops and 5 drops of
NaOH. Concentrated HCl added to neutral. of 5% sodium sodium
Then added 5 drops of FeCl3 and observe bicarbonate bicarbonate
the changes that occur. solution little gas bubbles
are formed
KMnO4 test Colorless
Note the release of
The KMnO4 test was carried out by solution
gas from the test
inserting 0.1 g / 1mL of acetic acid, tube
benzoate and salicylate respectively into a
reaction tube. 2 drops of KmnO4 were
Note the changes
added and observed changes occurred
that occur

AgNO3 and Base Tests

AgNO3 and alkaline tests were
carried out by means of acetic acid and Distinguishing Mono and Poly
oxalic acid into 1 ml of each test tube. 5 Carboxylates
Treatment Observation
drops of AgNO3 solution were added and
observed changes occurred. Then heated
and observed changes that occur. A Oxalic acid and Acetic acid 5
procedure similar to the addition of Ba acetate are added drops plus
(OH) 2 is carried out. to each test tube FeSO4 5 drop of
cloudy solution
Set of tools Plus clear
solution NaOH
Oxalic acid 5
drops plus
Picture 1. FeSO4 5 drops
A series of
carboxylic acid
and esters
 Add 3 drops of Treatment Observation
FeMO4 1M and of solution
KOH solution or becomes clear
NaOH as much as yellow
5 drops Plus the NaOH Add 0.1 g / ml of
solution acetate, benzoate
becomes green and salicylate 0.5 acetic acid plus
and there is respectively in KmnO4 clear
Observed the different test tubes concentrated purple
black sediment
results obtained solution
0.5 benzoic acid plus
KmnO4 concentrated
purple solution and
Added with 2 drops
there is a gel
Sediment Test with FeCl3 of KmnO4 solution
0.5 salicylic acid plus
KmnO4 in a black
Treatment Observation solution and gelatin
Observed the
changes that
Put benzoic acid
occurred
into the test tube
and dissolve it in
NaOH Benzoic acid plus
clear solution
NaOH AgNO3 and Base Tests
Concentrated
Plus concentrated
HCl added to
HCl has white
neutral Treatment Observation
deposits and white
solutions
Next, FeCl3 5 Oxalic acid plus
Plus the yellow Put into 3 test
drops is added AgNO3 solution
solution FeCl3 and tubes 1 ml of
white gelatin forminic acid is cloudy
Observed the acetate and Heated white
changes that oxalate sediment and
occurred colorless solution
Acetic acid plus
Add 5 drops of AgNO3 solution
AgNO3 solution is cloudy
Heated white
Observed the sediment and
changes that colorless solution
occurred
Oxalic acid plus
Heated up Ba (OH) 2

KMnO4 test
 Observed the
changes that
occurred
The same
colorless solution
procedure is done
and white gel
with the addition
Heated there was
of Ba (OH) 2
no change
Acetic acid plus
Ba (OH) 2
Discussion
Carboxylic acid is the most
important compound, the effect of heat on
various carboxylic acids affects the distance
of the carboxylic group. Oxalic acid breaks
down into CO2 and formic acid which
breaks down into CO and H2O. Acid can be
produced from the oxidation of the
aldehyde or in wine to acetic acid. The
acetic acid solution formed by this method
is vinegar. The name suffix for organic is
-oat added to the acidic word in front of it
(Hart, 2003).
Carboxylic acid is a group of
organic compounds characterized by a
carboxyl group, namely the name derived
from the name of the carbonyl and hydroxyl
functional groups. The general formula for
carboxylic acid is RCOOH. Carboxylic
acids are classified as acids because these
compounds ionize in solution, produce
carboxylic ions and protons (Wilbraham,
1992).
Figure 2.
Structure of carboxylic acid
Carboxylic acids have several
species or types. The types of carboxylic
acids are as follows (Respati, 1986):
a. Acid Halide
Acid halides are the most reactive
derivatives of carboxylic acids. The
reactivity of the carboxylic acid derivative
is determined by the clarity of the group
leaving it. Weak bases are more
electronegative, but it is also less likely to
donate electrons to carbonyl carbon through
a resonance effect. The halide ion is a very
weak base because the conjugate acid is a
strong acid. Therefore, halide acid is more
reactive than other carboxylic acid
derivatives.
b. Carboxylic Acid Anhydride
Acid anhydride has two molecules
of carboxylic acid in which a molecule of
water is removed. (Anhydride means "a
compound without water"). For example,
two molecules of ethanoic acid and
removing one water molecule are obtained
ethanoic anhydride (old name: acetic
anhydride).
c. Carboxylic Acid Esters
Esters are organic compounds that
are very useful and can be converted into
other compounds. Esters are formed
through one or more substitutes of
hydrogen atoms in the hydroxyl group with
an organic group. Esters are often found in
nature such as fat and wax. Essential oils
cause in many fruits and perfumes.
d. Amida
Amides are compounds that are
not very reactive, because proteins consist
of amino acids connected by amide bonds.
Amide does not react with halide ions,
carboxylic ions, alcohol, or water because
in each case, the incoming nucleophile is a
weak base of the amide leaving group.
Amide can react with water and alcohol if
the reaction mixture is heated in an acidic
atmosphere.
c. Nitrile
Nitrile is an organic compound
containing triplicate between carbon and
nitrogen atoms. The functional group in the
nitrile is a cyano group.
Esters are polar molecules and also
have a lower boiling point than carboxylic
acids and also alcohols with similar
molecular weight because hydrogen bonds
between molecules between ester molecules
are not possible. Esters can be from
hydrogen bonds through their oxygen atoms
with hydrogen atoms from water molecules.
Thus, esters are slightly soluble in water.
However, because esters do not have
hydrogen atoms to form hydrogen bonds of
oxygen atoms with water, they are less
soluble with carboxylic acids (Ouellette and
Robert, 1994).
Esterification is an ionic reaction, in
which the combination of the addition
reaction and the Esterification elimination
rearrangement reaction is the reaction of
converting from a carboxylic acid and
alcohol to an ester using an acid catalyst.
This reaction is also often called Fischer
esterification. Esters are compounds that
contain the -COOR group with R can be in
the form of alkyl or aryl. An ester can be
formed by an acidic catalyst esterification
reaction. An esterification reaction is a
reversible reaction (Hoydockx, 2004).
An esterification reaction is an ester
formation reaction by refluxing a
carboxylic acid with an alcohol with an acid
catalyst. The acid used as a catalyst is
usually sulfuric acid. The formation of
esters through direct acylation of carboxylic
acid against alcohol, such as in Fischer
esterification is preferable to acylation with
acid (low atom) or acyl chloride anhydride
(sensitive to humidity). The main
disadvantage of direct acylation is the low
chemical equilibrium constant. This must
be overcome by adding a lot of carboxylic
acid, and separating the water that is the
result of the reaction. Water separation is
carried out through Dean-Strak distillation
or the use of molecular sieves (Usman,
2013).
Figure 3.
Esterification reaction
The experiments of carboxylic
and ester acid compounds were carried out
aimed at identifying carboxylic acid
compounds and esters, studying the
physical properties and solubility of
carboxylic acid compounds and esters and
knowing how to make esters using the
esterification method.
a. Carboxylic acid
The first step taken in this
experiment was the identification of
carboxylic acids by means of a solution
containing 5 carboxylic acids, salicylic
acid, which was taken into the reaction
pond. Add 5 drops of NaHCO3 to the
solution. After adding NaHCO3 a few gas
bubbles arise and a colorless solution.
Carboxylic is a salt that behaves
like organic salt, odorless, relatively high
melting point and often easily soluble in
water. Because of the shape of the ion, it is
difficult to dissolve in organic solvents.
Sodium salt from long carbon carboxylic
acids is called soap (Daintith, 1994).
b. Esther's formation
The formation of the ester is done
by inserting 1 ml of salicylic acid into the
test tube and adding 2 ml of ethanol and 5
drops of sulfuric acid. After addition of
ethanol and sulfuric acid the solution
becomes clear and has a hot temperature.
The addition of H2SO4 in this experiment
functions as a catalyst. Eserifikasi reaction
is a reversible reaction that is very slow, but
when using a mineral acid catalyst such as
sulfuric acid, equilibrium will be achieved
in a fast time. Then heated and added with
sodium bicarbonate. After addition of
sodium bicarbonate gas bubbles arise and a
little smell of esters. In general the reaction
is: RCOOH + R’OH → RCOOR + H2O
c. Distinguish mono and poly carboxylates
Identification of mono and poly
carboxylates was carried out by means of
oxalic acid and acetic acid put into 2
different test tubes and then added 5 drops
of FeSO4 solution. In a solution of oxalic
acid the solution is clear yellow, and in the
solution of acetic acid is cloudy. Next
NaOH is transplanted into the game. In a
mixture of oxalic acid solution the solution
changes from clear yellow to green and
black deposits are applied, and the solution
of acetic acid solution becomes clear.
Oxalic acid solution plus FeSO4
and NaOH indicates mono carboxylic
formation. Where in this oxalic acid
solution does not form deposits, and dark
colored solutions. Whereas in acetic acid
solution indicates the formation of poly
carboxylates. This poly carboxylate is
characterized by the formation of deposits
in acetic acid solution.
Carboxylic acid is an organic
compound containing the carbonyl group
-CO2H. The carboxyl group is a group
containing a carbonyl group and a hydroxyl
group. The interaction between these two
groups results in a unique chemical
reactivity for carboxylic acids. Aspirin is a
carboxylic acid because the carboxyl group
is polar and does not block so that the
reaction is not too affected by the rest of the
molecule. The molecular-weighted acids are
low soluble in water or in organic solvents
(Fessenden, 1982).
d. Deposition test with FeCl3
The deposition test with FeCl3
was carried out by means of benzoic acid
inserted into the test tube and added by
clear solution NaOH. Added concentrated
HCl clear solution and white deposits. Then
added with FeCl3 the solution changes
from clear to yellow and the color of the
sediment is white
e. KMnO4 test
KMnO4 test was carried out by
0.5 acetic acid, benzoic acid and salicylic
acid added with KMnO4. In acetic acid the
concentrated purple solution is clear. In a
solution of concentrated purple benzoic
acid and there is a gel, and in a solution of
salicylic acid the solution is black and there
is a gel.
KMnO4 acts as a catalyst. The
aim of adding KMnO4 is to determine the
oxidation reaction. KMnO4 is a strong
oxidizing agent. An oxidation reaction
occurs when the purple color of KMnO4 is
lost from the mixture.
f. AgNO3 and base test
The AgNO3 and base tests are
carried out by means of an oxalic acid
solution plus AgNO3 solution which is
cloudy and when heated the solution turns
clear and the formation of white deposits.
The formation of these deposits indicates
that Ag has acted with oxalic acid. Next a
solution of oxalic acid plus Ba (OH) 2 is a
colorless solution and when the solution is
heated there is no change. This indicates
that the carboxylic acid is soluble in basic
solvents and is insoluble in acid solvents.
CONCLUSION

Based on the experiments that

have been done, it can be concluded that:
1. A carboxylic acid is an organic
compound containing the -COOH
group. Esters are carbon compounds
containing the -COO-group
2. Carboxylic acids and esters dissolve
in alkalan base, and are difficult to
dissolve in acidic solutions.
3. An ester can be made by reacting
carboxylic acid with an alcohol with
an acid catalyst.

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