Carboxylic acids and derivatives

L. Maminta1, R. Sagun2, S. Nota3

1 Departmentof Physical Sciences, College of Science, UP Baguio, Baguio City 2600
Performed 18 October 2019; Submitted 6 October 2019

ABSTRACT

Carboxylic acids contain the carbonyl group and a hydroxyl group that is attached to the carbonyl carbon. A
chief characteristic of this group is that it is the most acidic among all organic compounds due to the
combination of the carbonyl and hydroxyl groups. The basis of acid strength is the stability of the consequent
ion that is formed after proton removal. Due to the acidity of the carboxyl group, it is prone to nucleophilic
attacks and thus gives rise to a family of related organic derivatives. In this experiment, two carboxylic acid
representatives namely; acetic and benzoic acid were found to be soluble in the weak base 5% NaHCO 3. Acetic
acid and benzoyl chloride were synthesized to produce a sweet odor, indicating that both compounds
produced ester through esterification of carboxylic acid. The carboxylic derivative samples namely; acetic
anhydride, benzamide, and ethyl acetate underwent hydrolysis. Observations indicate that the parent
compound was regained. The test for the presence of carboxylic acid in acetic acid and benzoic acid through
mixture with FeCl3 gave positive results. It was also found that the reducing capacity of oxalic acid was greater
than that of formic acid.

strong bases like NaOH. Generally, the more the

Introduction delocalization of the negative charge in the
conjugate base, the more stable the anion is and the
Like aldehydes and ketones, carboxylic acids also more acidic the compound becomes (Solomons &
contain the carbonyl functional group (C=O). The Fryhle, 2011).
difference is that, instead of a hydrogen or an alkyl
group, the hydroxyl group (-OH) is attached to the Carboxylic acids are polarized. Their molecules can
carbonyl carbon. Thus, the functional group form strong hydrogen bonds with each other and
exhibited by carboxylic acids is termed carboxyl with water. As a result, carboxylic acids have the
group (Department of Physical Sciences, 2017). highest boiling point among organic compounds
and low-molecular-weight carboxylic acids show
appreciable solubility in water. The carboxyl group
is the parent group of a large variety of related
compounds. Several nucleophiles may attack the
Figure 1. General structure of carboxylic acids. carboxyl group to form a number of carboxylic acid
derivatives known as acyl compounds (Solomons &
The central chemical characteristic of this group is Fryhle, 2011). These include acyl halides,
its greatest acidity among all organic compounds anhydrides, esters, and amides.
due to the combination of the carbonyl and
hydroxyl groups. The primary factor in
determining the relative acid strength of
compounds is the nature of the carboxylate ion
formed consequent to removal of the hydroxyl
proton. The carboxyl group and carboxylate anion
exhibit resonance but the anion experiences a more
effective delocalization of the negative charge thus
greater stabilization than its neutral form. Two
resonance contributors give equal weight to the
hybrid resulting to increased acidity of the
Figure 2. General structure of carboxylic acid
molecule (Reusch, 1999). Electronegative
derivatives.
substituents increase the acidity of the compound
by inductive electron withdrawal. Such compounds
are soluble in both weak bases like NaHCO3 and
Esters and amides are important derivatives as
these have close associations with natural
products, proteins, and pharmaceuticals. Acyl
halides are most commonly used to synthesize
other related derivatives due to the high reactivity
of the halide substituent. Anhydrides are derived
through the dehydration of two carboxylic acids
and are commonly used to manufacture industrial
products like polymers or plastics (Brown & March,
2018).
The parent compound may be resynthesized from
acid derivatives through either acid or base-
catalyzed hydrolysis. The presence of carboxylic
acids is indicated by the formation of colored
complexes upon reaction with FeCl3. Benzoic acid
gives a flesh-colored precipitate while acetic acid
gives a red solution (Department of Physical
Sciences, 2017).
In this experiment, the objectives were; 1) to
compare the solubility of acetic acid and benzoic
acid, 2) to synthesize esters from carboxylic acid
and from acyl halide, 3) to resynthesize the
carboxylic acid from acetic anhydride, amide, and
ester, 4) to determine the presence of acetic and
benzoic acids through reaction with FeCl3, and 5) to
observe the reducing property of formic and oxalic
acids.
Methodology
In this experiment, five (5) major tests were
performed to synthesize and examine carboxylic
acids and derivatives.
In part 1, solubility of carboxylic acid in 5% NaHCO3
was tested. In two separate test tubes, 5 drops each
of acetic acid and a pinch of benzoic acid was
placed. Then 3.00 mL of 5% NaHCO was added to
3 drops of FeCl was added into the solution.
the solution. Any observable changes in the
solution was noted.
For part 2, formation of esters from carboxylic
acids and acyl halides was done. For part 2A,
carboxylic acid was used as a precursor in the
formation of esters. To 10 drops of acetic acid, 1 mL
of ethanol and 5 drops of concentrated H SO were
2 4
added. the mixture was warmed in a 60 C water
o the permanganate solution stopped. Observations
bath. A sweet smell of the solution was observed.
The product was then set-aside. In part 2B, acyl
halide was used to form ester, a reaction also called
Schotten-Baumann Reaction. Into a test tube, 1.00
mL of ethanol and 3.00 mL of water was placed.
Then 5 drops of benzoyl chloride were added to the
solution. The test tube was covered with cork
stopper and mixed. Into the solution, 3.00 mL of
20% NaOH was gradually added with vigorous
shaking. Odor of the solution was noted.
Hydrolysis of acid derivatives was performed in
part 3. This teste was furtherly divided into three
tests. For the first test, 2.00 mL of water was placed
into a test tube. then 1.00 mL of acetic anhydride
was added. The acidity of the mixture was tested by
placing a piece of blue litmus paper at the mouth of
the test tube. For the second test, a pinch of
benzamide added with 5.00 mL of 10% NaOH were
placed into a test tube. the mixture was heated at
60 C water bath for 3-5 minutes. The odor of gas
o
evolved was noted. The acidity of the mixture was
tested by placing a piece of moist red litmus paper
at the mouth of the test tube. For the third part of
hydrolysis, 2.00 mL of ethyl acetate reared in part
2A was added with 5.00 mL of 6.00 M NaOH. The
mixture was heated in a water bath for 30 minutes.
The disappearance of the sweet smell of ester was
observed. The resulting mixture was then
neutralized with 6.00 M HCl. The odor of the
resulting solution was, again, observed.
In part 4, the reaction of carboxylic acids with FeCl3
was examined. For part 4A, 3.00 mL of 10% NaOH
was placed in a test tube. Acetic acid was added
until the solution became slightly acidic. Few drops
of FeCl solution was added. For part 4B, 2.00 mL of
3
water was placed into a test tube. Then, a pinch of
benzoic acid was added. The mixture was heated to
dissolve the solid. When the solution was cool
enough, 10% of NH was added until the solution
3
was slightly basic. The test tube was placed in a
boiling bath to evaporate the excess NH The 3.
procedure was done in the hood. Afterwards, 2
3
Observations were recorded.
For the last part, the reducing property of some
acids was tested. In two separate test tubes, 1.00
mL each of formic acid and oxalic acid was placed.
Then, 2.00 mL of dilute H SO was added, and was
2 4
heated gently. Next, 0.10% KMnO was added drop
4
by drop, with shaking, until the decolorization of
and the number of drops of KMnO added were
4
recorded.
Results and Discussion
A. Solubility in 5% NaHCO3
Both and carboxylic acids are known to be a polar
compounds. Recalling the principal rule of
solubility which is “like dissolves like“, we can infer
that 5% 𝑁𝑎𝐻𝐶𝑂3 dissolves both acetic acid and
benzoic acid. Furthermore, we must note that
𝑁𝑎𝐻𝐶𝑂3 will deprotonate functional groups with a
pKa of less than 8, which include carboxylic acids.
This reaction is due to the neutralization of both
acid and base properties to produce salt (made of a
metal ion and a non-metal ion), water and carbon
dioxide. Acetic acid (𝐻𝐶2 𝐻3 𝑂2 ) with 5% 𝑁𝑎𝐻𝐶𝑂3
undergoes a reaction called double replacement. A
double-replacement reaction is a reaction in which
the positive and negative ions of two ionic
compounds exchange places to form two new
compounds. The following reaction is as follows:
HC2H3O2 + NaHCO3  NaC2H3O2 + H2CO3 
NaC2H3O2 + H2O +CO2
For benzoic acid (𝐶6 𝐻5 𝐶𝑂𝑂𝐻) with 5% 𝑁𝑎𝐻𝐶𝑂3 to
form water, two hydrogen atoms for every oxygen
is needed. Thus in the balanced equation, you will
have 2 benzoic acids for every sodium carbonate as
follows:
2C6H5COOH + NaHCO3  2C6H5COONa + H2CO3 
2C6H5COONa + H2O +CO2
This will also mean that you have provided two
benzoate ions, which will be necessary as the
formula for sodium carbonate shows there are two
sodium ions joined to every carbonate.
Generally, the reaction converts the acid into its
more soluble conjugate base which is also a factor
of the solubility of both carboxylic acids. As an
additional observation, when bicarbonate
solutions are treated with acids they react to form
𝐶𝑂2 which bubbles out of solution. Hence, the
bubbling of the solution.
B. Formation of esters
The reaction being observed in this test is
esterification. Esterification occurs between an
acid, usually carboxylic acid and an alcohol or any
compound containing the hydroxyl group where
esters are obtained. Most carboxylic acids are
suitable for this reaction, but the alcohol should
generally be a primary or secondary alcohol hence
the use of ethanol. Upon the addition of a catalyst
such as concentrated 𝐻2 𝑆𝑂4 , the carboxylic acid
and alcohol combine in an equilibrium process to
give ester and water. The presence of the acid
catalyst in the mechanism of ester formation aids
in making the carbonyl carbon more electrophilic
and undergo nucleophilic attack. Moreover, the
protonation of the hydroxyl group gives water,
which is a superior leaving group (i.e. weaker base)
in the elimination step. An indication of the
formation of an ester is the change in smell of the
mixture. Esters are usually manifested by its fruity
characteristic odor.
Being a carboxylic acid, acetic acid follows this
mechanism to form esters. Generally, acetic acid
reacts with ethanol in the presence of concentrated
sulphuric acid (𝐻2 𝑆𝑂4 ) as a catalyst to produce the
ester, ethyl ethanoate. The reaction is as follows:
Figure 3. Reaction of acetic acid with ethanol and
concentrated sulphuric acid.
Benzoyl chloride, on the other hand, is a typical acyl
chloride which reacts with alcohols to give the
corresponding esters. Benzoyl chloride has the
formula 𝐶6 𝐻5 𝐶𝑂𝐶𝑙. The –COCl group is attached
directly to a benzene ring. It is much less reactive
than simple acyl chlorides like ethanoyl chloride
thus it can undergo esterification. Unlike acetic acid
which needs concentrated 𝐻2 𝑆𝑂4 catalyst to react,
benzoyl chloride readily reacts with an alcohol to
produce esters as shown in the figure:
Figure 4. General reaction of benzoyl chloride
with alcohols
 C. Hydrolysis of Acid Derivatives
Hydrolysis of acid derivatives is one of the methods
to synthesize carboxylic acids. All acid derivatives
can be hydrolyzed or cleaved by water to yield
carboxylic acids (Brown & March, 2018). In a
hydrolysis reaction, a chemical bond is broken by
the addition water. Hydrolysis is typically carried
out in the presence of a salt of a weak acid or weak
base. Water autoionizes into hydroxyl ions (- OH)
and hydronium ions (H3O+ ) and acts as a source of
a nucleophile and catalyzing acid, but it is also a
weak acid and in most cases hydrolysis in water is
too slow for the reaction to proceed without the
addition of a strong acid (Antic, 2014). Acyl
chlorides are the easiest acid derivatives to
hydrolyze which requires only the addition of
water (Brown & March, 2018).
Carboxylic esters, nitriles, and amides are less
reactive. They must be heated with water and a
strong acid or base to yield the corresponding
carboxylic acid. Among these three acid
derivatives, amides are the least reactive and
require the most vigorous treatment like higher
temperature (Brown & March, 2018).
Hydrolysis of acetic anhydride was done first. The
hydrolysis of acetic anhydride in the presence of
water is an exothermic reaction that produces
acetic acid. (Fritzler, Dharmavaram, Hartrim, &
Diffendall, 2014). Acetic anhydride exhibits the
same reactions as acyl chloride, although it
generally reacts more slowly. Like acyl chloride, it
rapidly hydrolyzes in the presence of water. It
actually reacts with water in the air, and is a
lacrimatory (a substance that increases or triggers
the production of tears) (Brown & March, 2018). In
the experiment, as the compounds were mixed,
evolution of heat was observed. This was a
manifestation that the reactive was positive.
Furthermore, when the blue litmus paper was
brought at the mouth of the test tube, the color
gradually turned into red. Litmus paper is used to
test the pH balance of a liquid or substance. When
red litmus paper is placed into a basic substance,
it will turn blue. When blue litmus paper is placed
in a substance that is acidic, it will turn to red
(Hanson, 2018). The hydrolysis of acetic
anhydride, therefore, yielded a carboxylic acid
since the blue litmus paper turned into red which
is an indication that an acidic compound is
present. The chemical equation for the hydrolysis
of acetic anhydride is shown below.
(𝐶𝐻3 𝐶𝑂)2 𝑂 + 𝐻2 𝑂 → 2𝐶𝐻3 𝐶𝑂𝑂𝐻
Secondly, the hydrolysis of benzamide was
performed. Amides are the least reactive because
they have the poorest leaving group among the
carboxylic acid derivatives. Under strenuous
reaction conditions, amides are hydrolyzed in acid
or base to form carboxylic acids or carboxylate
anions (Smith, 2008). In acid, carboxylic acid is
formed and the amine by-product is protonated as
an ammonium ion, whereas is base, a carboxylate
anion is yielded, and a neutral amine or ammonia is
formed. The chemical equations are shown below.
Hydrolysis of amide in an acid
𝐶𝐻3 𝐶(𝑂)𝑁𝐻2 + 𝐻2 𝑂 + 𝐻 + → 𝐶𝐻3 𝐶𝑂𝑂𝐻 + 𝑁𝐻4
Hydrolysis of amide in a base
𝐴𝑟𝐶(𝑂)𝑁𝐻2 + 𝐻2 𝑂 + 𝐻𝑂 − → 𝐴𝑟𝐶𝑂𝑂+ + 𝑁𝐻3
In the experiment, a pinch of benzamide was added
with 5.00 mL of 10% NaOH and heated at 60o C
water bath for 3-5 minutes. A change in odor was
observed. Initially, the mixture was odorless. An
unpleasant smell evolved after the procedure. The
change in odor is an indication that the reaction
was positive. Furthermore, when the red litmus
paper was brought at the mouth of the test tube, the
color changed into blue. This is an indication that a
basic or alkaline compound was formed.
Carboxylate anion and ammonia were the products
of the hydrolysis of amide in basic condition.
Ammonia is a base and carboxylate anion is a
conjugate base of carboxylic acid, therefore, the
color change of red litmus paper into blue is
justified. The chemical equation for the hydrolysis
of benzamide under 10% NaOH is shown below.
𝐴𝑟𝐶(𝑂)𝑁𝐻2 + 𝐻2 𝑂 + 𝑁𝑎𝑂𝐻
→ 𝐴𝑟𝐶𝑂𝑂− 𝑁𝑎 + + 𝑁𝐻3
The hydrolysis of a carboxylic ester was done in the
third part. Ethyl acetate was used as a test
compound. Esters are hydrolyzed with water in the
presence of either acid or base to form carboxylic
acids or carboxylate anions (Smith, 2008). The
hydrolysis of esters in aqueous acid is a reversible
equilibrium reaction, whereas the hydrolysis of
ester in aqueous base is irreversible (Smith, 2008).
Basic hydrolysis of an ester is called saponification.
It forms carboxylate anion and alcohol, while
carboxylic acid is formed in acidic hydrolysis.
Chemical equations are shown below.
Hydrolysis of ester in an acid
𝐶𝐻3 𝐶𝑂𝑂𝐶𝐻2 𝐶𝐻3 + 𝐻2 𝑂 + 𝐻 + → 𝐶𝐻3 𝐶𝑂𝑂𝐻
Hydrolysis of ester in a base
𝐶𝐻3 𝐶𝑂𝑂𝐶𝐻2 𝐶𝐻3 + 𝐻2 𝑂 + 𝐻𝑂 −
→ 𝐶𝐻3 𝐶𝑂𝑂 − + 𝐶𝐻3 𝐶𝐻2 𝑂𝐻
In the experiment, 2.00 mL of ethyl acetate was
added with 5.00 mL of 6.00 M NaOH and heated in
a water bath for 30 minutes. The sweet smell of the
ester was observed to have turned into an
unpleasant smell. This was an indication that the
ester was already reacted with the reagents. The
chemical equation of the reaction was shown
below.
𝐶𝐻3 𝐶𝑂𝑂𝐶𝐻2 𝐶𝐻3 + 𝐻2 𝑂 + 𝑁𝑎𝑂𝐻
→ 𝐶𝐻3 𝐶𝑂𝑂 − 𝑁𝑎+ + 𝐶𝐻3 𝐶𝐻2 𝑂𝐻
Afterwards, the resulting mixture was neutralized
with 6.00 M HCl. White precipitate was formed. The
equation is shown below.
𝐶𝐻3 𝐶𝑂𝑂 − 𝑁𝑎+ + 𝐻𝐶𝑙 → 𝐶𝐻3 𝐶𝑂𝑂𝐻 + 𝑁𝑎𝐶𝑙
Sodium acetate reacted with hydrogen chloride (an
acid) and produced acetic acid (carboxylic acid)
and sodium chloride (salt).
D. Reaction with FeCl3
Acid derivatives react with nucleophiles to form a
tetrahedral intermediate which, through loss of a
leaving group, gives the product. In this process,
acyl transfer occurs from the acid derivative to the
nucleophile. Acetic acid is an acyl halide that reacts
with FeCl3 indicated by the formation of red-
colored precipitate. However, higher acidity can
interfere in the final results therefore should be
made neutral hence the addition of NaOH. This
reaction produces sodium acetate and water. The
reaction is as follows:
3CH3COOH + FeCl3  Fe(CH3COO)3 + 3HCl
Benzoic acid changes color with FeCl3 due to the
formation of salts. Nota that to form salts,
carboxylic acids are neutralized by bases in a
manner similar to that of inorganic acids.
Neutralization of carboxylic acid produces salt and
water. The formation of flesh-colored precipitate
was observed during the reaction. The reaction is
as follows:
3C6H5COOH + FeCl3 → Fe(C6H5COO)3+3HCl
E. Reducing property of some acids
Oxalic acid is also known as ethanedioic acid. In
reaction with KMnO4, it acts as a reducing agent
while potassium permanganate acts as an oxidizing
agent. Since this reaction takes place in the
presence of dilute sulfuric acid, the oxidizing
power of the permanganate ion is increased. The
KMnO4 exhibits the deep purple color of the
permanganate ions MnO4– and it acts as the
indicator of the chemical reaction with oxalic acid
as the oxalate ion C2O42- will decolorize the
permanganate (Brown, 2019). This reaction occurs
very slowly at room temperature which is why the
solution should be warmed gently. In this test, the
oxalic acid decolorized 30 drops of potassium
permanganate. This indicates that the MnO4- was
reduced to colorless manganous ions (Mn2+) in the
acidic medium. The succeeding drops produced an
increasing pinkish to reddish brown color. The first
drop that is not decolorized indicates the
equivalence point of the permanganate and oxalate
ions. Potassium permanganate reacts with oxalic
acid and sulfuric acid to produce manganese (II)
sulfate, carbon dioxide, potassium sulfate and
water. The balanced equation for this reaction is as
follows:
2KMnO4 + 5H2C2O4 + 3H2SO4 → 2MnSO4 + 10CO2 +
K2SO4 + 8H2O
Formic acid is a distinct carboxylic acid that is
characterized by its weak acid strength, failure to
form an anhydride, and its reactivity as a reducing
agent. In reaction with KMnO4 in the presence of an
acid, the purple color disappears to form a red-
brown complex due to the presence of a crystalline
compound with the formula
(K2{Mn(H2O)2[Mn3O](HCOO)9]2} (Lis &
Trzebiatowska, 1976). In this test, the formic acid
was able to reduce 8 drops of potassium
permanganate and the intense purple color
combined with the colorless formic acid exhibited
a rusty color. The final products are the same with
oxalic acid. The overall reaction between
permanganate and formic acid is expressed in the
following equation:
5HCOOH + 2KMnO4 + 3H2SO4 → 5CO2 + 8H2O +
K2SO4 + 2MnSO4
In comparison, the oxalic acid was able to reduce a
greater amount of potassium permanganate. This
is attributed to the significant difference of their
acid strengths. Since acidity is generally measured
by the ease of giving away a proton and reduction
indicates an increase in hydrogen or a decrease in
oxygen atoms, then a stronger acid is consequently
a stronger reducing agent (McMurry, 2010). Oxalic
acid is more acidic than formic acid due to the
presence of two carbon atoms and two double
bonds thus providing a more effective
delocalization of negative charge. Theoretically,
the oxalic should be able to reduce more KMnO4. In
this experiment, it reduced 30 drops of potassium
permanganate as denoted by the decolorization of
the purple compound while formic only
decolorized up to 8 drops. Thus, the experimental
results agree with the theoretical.
Conclusion and Recommendations
Carboxylic acids are organic acids with one or more
carboxylic acid groups. Their properties vary
significantly with their carbon-chain length,
molecular structure, and the presence of additional
functional groups. The experiment aimed to
observe the different reactions of carboxylic acid
under various tests. Carboxylic acid test
compounds were first subjected to a solubility test
with 5% NaHCO3 as solvent. Both acetic acid and
benzoic acid yielded positive results primarily due
to their similar polarity. Test compounds were also
tested for esterification wherein acetic acid and
benzoyl chloride were both transformed into
esters which was manifested through the change in
odor of the solution. Both solutions manifested
fruity and sweet odors which is an indication of
ester formation. Test compound were also tested
for hydrolysis. It was observed that acetic
anhydride yielded a carboxylic acid since the blue
litmus paper turned into red which is an indication
that an acidic compound is present; benzamide
yielded carboxylate anion and ammonia while
ethyl acetate have acetic acid (carboxylic acid) and
sodium chloride (salt) as its final product. Hence,
all three test compounds yielded positive results.
Reactions of carboxylic acid with FeCl3 were also
observed wherein both acetic acid and benzoic acid
yielded positive results through the formation of
precipitate and change in color. Finally, the
reducing property of some acids were observed.
Oxalic acid decolorized 30 drops of potassium
permanganate. This indicates that the MnO4- was
reduced to colorless manganous ions (Mn2+) in the
acidic medium. Potassium permanganate reacts
with oxalic acid and sulfuric acid to produce
manganese (II) sulfate, carbon dioxide, potassium
sulfate and water. Formic acid, on the other hand,
was able to reduce a lesser amount of potassium
permanganate. This is due to the significant
difference of their acid strengths.
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APPENDIX