ORGANIC FUNCTIONAL GROUP

CARBOXYLIC
ACIDS
IVAN CHRISTIAN B. BANASTAO, LPT
OBJECTIVES

Describe Carboxylic Acids and their

Functional Derivatives;

Give name and draw the structures of Carboxylic

Acids and their Functional Derivatives

enumerate the different sources and uses of

Carboxylic Acids and their Functional Derivatives in
the industry and in our daily life;
OBJECTIVES

Correlate the structure of Carboxylic Acids and their

Functional Derivatives to their physical properties

present an equation on the preparations of

Carboxylic Acids and their Functional Derivatives;

write a chemical reaction and describe the reaction

mechanisms of Carboxylic Acids and their
Functional Derivatives.
INTRODUCTION
Carboxylic acids have been
known throughout human
history. Prehistoric people
likely made acetic acid when
their fermentation reactions
went awry and produced
vinegar instead of wine. The
Sumerians (2900–1800 BCE)
used vinegar as a condiment, a
preservative, an antibiotic, and
a detergent.
INTRODUCTION Vinegar contains 4 to 5 percent
acetic acid. Acetic acid gives
vinegar its sour taste and
pungent odor and can do the
same thing to wine. Acetic acid,
CH₃COOH, is an example of the
class of compounds
called carboxylic acids, each of
which contains one or more
carboxyl groups, COOH. The
general formula of a carboxylic
acid is RCOOH.
 Carboxylic
Acid
Structure

The general formula of a
carboxylic acid is R- In this carboxyl group,
COOH, were COOH there exists a carbon
refers to the carboxyl which shares a double
group, and R refers to the bond with an oxygen
rest of the molecule to atom and a single bond
which this group is with a hydroxyl group.
attached.
 Carboxylic
Acid
Structure

Continuous
carbon chain
Carboxylic Carboxyl
Group
Acid
Structure
 Carboxylic Carboxyl
Group
Acid
Structure

Continuous
carbon chain
Carboxylic
Acid
Structure

The first four carboxylic acids derived from alkanes

are methanoic acid (HCOOH), ethanoic acid
(CH₃COOH), propanoic acid (C ₂H ₅COOH) and
butanoic acid (C₃H₇COOH).
 Nomenclature of
Carboxylic Acids

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.
Nomenclature of
Carboxylic Acids Guideli
nes
The suffix “e” in the name of the The number of carboxyl groups is represented by
corresponding alkane is replaced with “oic Greek numeral prefixes such as “di-”, “tri-“, etc.
acid”.

When the aliphatic chain contains only one A carboxylic acid is named by adding these
carboxyl group, the carboxylic carbon is always prefixes and suffixes to the parent alkyl chain.
numbered one.

When the aliphatic chain contains more than one Arabic numerals are used for indicating the
carboxyl group, the total number of carbon atoms positions of the carboxyl group.
is counted
Nomenclature of
Carboxylic Acids

TRIVIAL NAME/ IUPAC NAME/

COMMON NAME SYSTEMATIC NAME
Formic Acid, H-COOH Methanoic Acid
Crotonic Acid, CH₃CH=CH-COOH 2-butenoic Acid
Carbonic Acid, HO-COOH Carbonic Acid
Butyric acid, CH₃(CH₂)₂COOH Butanoic Acid
examples

Hexanoic acid
examples

3-pentenoic
acid
 examples

4-oxohexanoic
acid
 examples

Cyclohexane
carboxylic acid
 6
5 1

4 2
examples

H₃C 3
Br

2-bromo-4-methyl- cyclohexane
carboxylic acid
 O O
3
5 4 1
6 2
OH
examples

OH

4-hydroxy-5-oxohexanoic acid
examples

Butanedioic acid
examples

Benzoic acid
examples

Toluic acid
• 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.
Properties of
Carboxylic Acids
Physical Properties
• 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.
 Physical Properties

• The solubility of
compounds
containing the
carboxyl functional
group in water
depends on the size
of the compound.
The smaller the
compound (the
Properties of shorter the R group),
the higher the
Carboxylic Acids solubility.
 Physical Properties
• The boiling
point of a
carboxylic acid • When placed in
is generally nonpolar solvents,
higher than these compounds
that of water. form dimers via
hydrogen bonding
between the hydroxyl
group of one
carboxylic acid and
the carbonyl group of
Properties of the other.

Carboxylic Acids
 Physical Properties

• These compounds
have the ability to
donate protons and
are therefore
Bronsted-Lowry
acids.
• They generally have a
strong sour smell.
However, their esters
Properties of have pleasant odours
and are therefore
Carboxylic Acids used in perfumes.
 Physical Properties

• The production of
soft drinks and many
other food products
involve the use of
many carboxylic
acids.

• The manufacture of
rubber/ cheese
Properties of involves the use of
acetic acid as a
Carboxylic Acids coagulant.
 Physical Properties

• 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

Properties of also used in the
manufacture of
Carboxylic Acids soaps.
 Physical Properties

• Hexanedioic acid
is used in the
manufacture of
nylon-6,6.
• Carboxylic acids • The synthesis of
have numerous many drugs involves
applications in the the use of these
rubber, textile, compounds.
and leather Therefore,
industries. carboxylic acids are
very important in
pharmaceuticals.

Properties of
Carboxylic Acids
 Physical Properties

Ethylenediaminetetraacetic acid is
a widely used chelating agent.

Properties of
Carboxylic Acids
 Uses of
carboxylic acid
 Uses of
carboxylic acid

• Carboxylic acids make up
a series of fatty acids
which are excellent for
human health. The
omega-6 and omega-3
are essential fatty acids
which are not produced
by the body. They help in
maintaining the cell
membrane and control
nutrient use along with
metabolism.
 Uses of • If we consume a meal with
unsaturated fat, the gluco
carboxylic acid se and other nutrients will
directly rush into the bloo
dstream without being abs
orbed. Whereas if there is
an intake of saturated fat,
digestion will slow down a
nd the body will get more t
ime to absorb the energy a
nd nutrients from the mea
l.
 Uses of • ●
Heating of a fat with a strong
carboxylic acid base such as sodium hydroxi
de (NaOH) or potassium hyd
roxide (KOH) to produce glyc
erol and the salt of a fatty ac
id (soap)
• ●When NaOH is used, a
solid soap will be formed,
whereas, when KOH is used,
a liquid soap will be formed.
 Carboxylic Acids and their
Functional Derivatives

Compounds such as acid

chlorides, amides, esters etc., are
called carboxylic acid derivatives
because they differ from a
carboxylic acid only in the nature
of the group or atom that has
replaced the – OH group of
carboxylic acid.
Carboxylic Acids and their
Functional Derivatives
 Carboxylic Acids and their
Functional Derivatives

Carboxylic acid anyhydrides

and acid chlorides, which also
fall under the carboxylic acid
derivative category, are not
generally found in
biomolecules but are useful
intermediates in laboratory
synthesis.
 Carboxylic Acids and their
Functional Derivatives
Carboxylic acid derivatives can
be distinguished from
aldehydes and ketones by the
presence of a group containing
an electronegative heteroatom
- usually oxygen, nitrogen, or
sulfur – bonded directly to the
carbonyl carbon.
You can think of a carboxylic
acid derivative as having two
sides. One side is the acyl
group, which is the carbonyl
plus the attached alkyl (R)
group.
Carboxylic Acids and their
Functional Derivatives

In the specific cases where R is a

hydrogen or methyl, chemists use the
terms formyl and acetyl group,
respectively.

One the other side is the heteroatom-

linked group: in this text, we will
sometimes refer to this component as
the ‘acyl X' group (this, however, is not
a standard term in organic chemistry).
 Notice that the acyl X
Carboxylic Acids and their
groups are simply Functional Derivatives
deprotonated forms of
other functional groups
linked to the acyl
group: in an amide, for
example, the acyl X
group is an amine,
while in an ester the
acyl X group is an
alcohol.
 Preparation and Uses of
Acid Halides Carboxylic Acid

• Methods of Preparation of
Acid Chloride:
• Acid chlorides are
prepared from carboxylic
acid by treating it with
anyone of the • This method is
chlorinating agent such as superior to
others as the by-
SOCl₂, PCl₅, or PCl₃ products being
1. By Reaction with Thionyl gases escape
Chloride (SOCl₂) leaving the acid
chloride in the
pure state.
• By Reaction of Acid Halide Preparation and Uses of
With a Salt of Carboxylic Carboxylic Acid
Acids

• Acid chlorides on heating

with sodium salt of
carboxylic acids gives
corresponding anhydride.

Acid
Anhydride
 Preparation and Uses of
Carboxylic Acid

We have already learnt that

treatment of alcohols
with carboxylic acids in
presence of mineral acid
gives esters. The reaction
is carried to completion
by using an excess of
reactant or by removing
the water from the
Esterification reaction mixture.
 Acid Amides Ammonolysis of Acid
Derivatives Preparation and Uses of
Acid amides are Carboxylic Acid
prepared by the action
of ammonia with acid
chlorides or acid
anhydrides.

Acid amides are derivatives

of carboxylic acid in which
the – OH part of carboxyl
group has been replaced
by – NH₂ group. Now, we
shall focus our attention
mainly on the study of
chemistry of acetamide.