UNIT 2

Chemistry of Carbon and Carbon

Compounds

Lesson 5:
Carboxylic Acid and Esters
DESIRED LEARNING OUTCOMES (DLO):
At the end of the unit, the students must have:
1. Wrote the common and IUPAC names of carboxylic acids.
2. Illustrated structural formulas for saturated carboxylic acid.
3. Wrote the common names, IUPAC names and formulas of esters.
4. Identified the portion of an ester that is derived from a carboxylic acid
and the portion derived from an alcohol.
5. Explained how a soap or synthetic detergent acts as a cleansing agent.

Whenever we eat food with a sour or tart taste, it is very likely that at least one
carboxylic acid is present in that food. For example, citric acid is present in lemons,
acetic acid is present in vinegar, and lactic acid ir present in sour milk. Carboxylic acids
are also important compounds in biochemistry. Citric acid is found in our blood, and
lactic acid is produced in our muscles during the breakdown of glucose. In living system,
these acids are most often found in the form of salts or acid derivatives. In the world
around us, we use carboxylic acid salts as preservatives, especially in cheeses and
breads, and to treat skin irritations like diaper rash and athlete’s foot.

Carboxylic acid derivatives known as esters are responsible for the sweet and
pleasant odors and tastes of our food. We frequently use these compounds as artificial
flavors in foods in place of more expensive natural extracts. In biochemistry, esterlike
molecules act as the energy carriers in many cells. As you will see, the properties of
carboxylic acids are quite distinct from those of aldehydes and alcohols.

5.1 CARBOXYLIC ACIDS

O
║
• Contains a carboxyl group , - C –OH or - COOH , - CO2H

Carboxylic acids can be either aliphatic or aromatic

5.2 NOMENCLATURE OF CARBOXYLIC

Aliphatic carboxylic acids form a homologous series. The carboxylic group is always
at the beginning of a carbon chain, and the carbon atom in this group is understood
to be the carbon number 1 when the compound is named.
_____________________________________________________________________
IUPAC Rules for Naming Carboxylic Acids
1. To establish the parent name, identity the longest carbon chain that includes
the carboxylic.
2. Drop the final e from the corresponding hydrocarbon name.
3. Add the suffix -oic acid.
_____________________________________________________________________

Thus the names corresponding to the one-, two-, and three-carbon acids are
methanoic acid, ethanoic acid and propanoic acid. These names are derived from
methane , ethane and propane:

CH4 methane HCOOH methanoic acid

CH3CH3 ethane CH3COOH ethanoic acid
CH3CH2CH3 propane CH3CH2COOH propanoic acid

Other groups bonded to the parent chain are numbered and named as we have
done previously. For example, we have

5 4 3 2 1
CH3-CH2-CH-CH2-COOH

CH3

3-methylpentanic

Table 5.1 IUPAC Names (Common Names) and Structural Formula of

Carboxylic Acid

IUPAC Name (Common Name) Structural Formula

Methanoic acid (Formic Acid) HCOOH
Ethanoic acid ( Acetic Acid) CH3COOH
Propanoic acid (Propionic Acid) CH3CH2COOH
Butanoic acid (Butyric Acid) CH3CH2CH2COOH
Pentanoic acid (Valeric acid) CH3CH2CH2CH2COOH
Hexanoic acid (caproic acid) CH3CH2CH2CH2CH2COOH

Organic acids are usually known by common names. Methanoic, ethanoic, and
propanoic acids are called formic, acetic, and propionic acids, respectively. These
names often refer to a natural source of acid and are not systematic. Formic acid gets
its name from the Latin word formica, meaning ant. This acid contributes to the
stinging sensation of ant bites. Acetic acid is found in vinegar and gets its name from
the Latin word for vinegar. The name butyric acid comes from the Latin term for butter,
since it is a constituent of butterfat. The 6-, 8-, and 10-carbon acids are found in goat
fat; their names are derived from the Latin word for goat. These three acids – caproic,
caprylic, and capric – along with butyric acid have characteristic and disagreeable
odors. In similar way, the names of the 12-, 14-, and 16-carbon acids – lauric, myristic
and palmitic – come from plants from which the corresponding acid has been isolated.
The name stearic acid comes from a Greek word meaning beef fat or tallow, which is
a good source of this acid. Many of the carboxylic acids- principally, those with even
numbers of carbon atoms ranging from 4 to about 20- exist in combined form in plant
and animal fats. These are called fatty acid. Table 24.1 lists the common and IUPAC
names, together with some of the physical properties, of the more important saturated
aliphatic acids.

5.3 PHYSICAL PROPERTIES OF CARBOXYLIC ACID

• Polar
• First four carboxylic acid, are completely soluble in water
• Acids with more than eight carbons are virtually insoluble in water
• Generally weak acids

5.4 CHEMICAL PROPERTIES OF CARBOXYLIC ACID

• Acid-base Reaction
- Sour taste
- Change blue litmus to red and effect other suitable indicators
- Form water solutions with pH values of less than 7
- Undergo neutralization reactions with bases to form water and a salt
 • Acid Chloride Formation

Acid + thionyl chloride acid chloride

• Acid Anhydride Formation

Acetyl chloride + sodium acetate acetic anhydride

• Ester formation

Carboxylic acid + alcohol ester

5.5 CLASSIFICATION OF CARBOXYLIC ACID

5.5.1 Unsaturated Carboxylic acid

• contain one or more carbon-carbon double bonds
• first member, acrylic acid, CH2 = CHCOOH: used to manufacture a class of
synthetic polymers known as the acrylate (are widely used as textiles and
in paints and lacquers)

https://i.visual.ly/images/acrylic-acid-market-is-expected-to-reach-188-billion-globally-by-2020_53b263060702f_w1500.jpg
5.5.2 Aromatic carboxylic acid
• Parent compound is benzoic acid

5.5.3 Dicarboxylic acid – contain two carboxyl group

• Simplest member is oxalic acid
Oxalic acid – found in various plants, including spinach, cabbage, and
rhubarb; use as bleaching straw and leather and removing rust and stains
and are poisonous
 Malonic acid – is made synthetically, but was originally prepared from
malic acid, which is commonly found in apples and many fruit juices; major
compounds used in the manufacture of the class of drugs known as
barbiturates

• Citric acid (tricarboxylic acid) – widely distributed in plant and animal tissue,
especially in citrus fruits
Citric acid has many uses in food production. It is a flavor enhancer,
preservative, and helps facilitate the ripening process. About 50 percent of
the world’s citric acid production is used as a flavor booster in beverages, and
because citric acid is made in a powder form, it's added to dry foods such as
seasoning salts, flavoring powders, and crunchy snacks when a sour flavor is
desired.

https://www.thespruceeats.com/what-is-citric-acid-1328465
 • adipic acid - is used to produce nylon; also used in polyurethane foams,
plasticizers, and lubricating-oil additives

https://mms.businesswire.com/media/20170516006527/en/587238/5/Adipic_Acid_Market.jpg

5.5.4 Hydroxy Acid

• Lactic acid – found in sour milk, sauerkraut, and dill pickles; contain of
both a carboxylic acid and an alcohol; end product when our muscles use
glucose for energy in the absence of oxygen, a process called glycolysis.
 • Salycylic acid (salicylates) – both a carboxylic acid and a phenol
Aspirin – function as analgesic (pain reliever) and as antipyretics (fever
reducers)

5.5.5 Amino Acids – has a carboxyl group that acts as an acid and an amino group
that acts as a base; found in every form of life

https://i0.wp.com/www.compoundchem.com/wp-content/uploads/2014/09/20-Common-Amino-Acids-v3.png?ssl=1
5.6 PREPARATION OF CARBOXYLIC ACID

5.6.1 Oxidation of an aldehyde or a primary alcohol

o Used to convert an aldehyde or primary alcohol to the
corresponding carboxylic acid

5.6.2 Oxidation of alkyl Groups attached to Aromatic Rings

COONa COOH

+ H+ + Na+

5.6.3 Hydrolysis of Nitriles

Nitrile (CH3CN) + 2H2O Carboxylic acid + NH4+

5.7 ESTERS
• is an organic compound formed by the reaction of an acid with an alcohol
or a phenol
• general formula for an Ester is RCOOR’
• found throughout nature
• fats and oils

Esters are used in many food industries because they are characterized by pleasant
smells and tastes, so they are used as flavours, Saponification is the hydrolysis of
fats or oils (triglyceride ester) in the presence of strong alkali as (NaOH) to produce
glycerol and sodium salt of the fatty acid (soap).

USES OF ESTERS

Fats and oils are esters produced from the reaction between fatty acids and glycerol,
their molecules are called triglyceride ester because each molecule is formed from the
reaction of one molecule of glycerol (trihydric alcohol) and three molecules of fatty
acids, the acid molecules may be similar or different, saturated long chain or
unsaturated short chain.

Esters are used in the manufacturing of soap, the hydrolysis of fats or oils (triglyceride
ester) in the presence of a strong alkali, such as (NaOH) or (KOH) to produce glycerol
and (sodium or potassium salt of fatty acid) is known as saponification process which
is the main reaction in the manufacture of soap.

Esters as polymers (polyester): Polyesters are polymers produced from the

condensation of two monomers, one of them is a dibasic acid and the other one is
dihydric alcohol, The most common polyester is Dacron fibers which are prepared by
the reaction between a terephthalic acid and ethylene glycol (ester formation reaction).

The condensation process proceeds continuously where the alcohol end of the ester
reacts with the carboxylic group of a new acid molecule or the acid end of the molecule
may be attached by a new alcohol molecule.
By the repetition of the condensation process, a very long molecule, which is called
polyester is formed, since Dacron is an inert polymer, so, it is used to substitute the
spoiled arteries and in the manufacture of artificial heart valves.

Polyesters are the polymers produced from the condensation of two monomers, one
of them is a dibasic acid and the other one is a dihydric alcohol, Dacron is the polymer
produced by the reaction between terephthalic acid and ethylene glycol, Esters are
used in manufacturing of textiles because the esterification of terephthalic acid with
ethylene glycol produces polyester which is used in dacron fibers industry.

Esters as medical drugs: Organic esters are used in the manufacture of many drugs
such as Aspirin and Marookh oil, the most common and simplest one is aspirin, oil of
wintergreen (Marookh oil) is used as a local oil absorbed by the skin to decrease the
pains of rheumatism, The acid which is used in the manufacture of these two drugs is
salicylic acid, its molecule contains both the carboxylic and hydroxyl groups, It reacts
as an acid or as an alcohol.

Aspirin is the important drug which reduces the headache pains and temperature, it
also reduces the blood clotting and prevents the heart crises, the active substance in
aspirin is salicylic acid, however, the addition of acetyl group (CH3CO–) to the acid
decreases its acidity effect and becomes tasteless, Aspirin is hydrolyzed in the body
to produce salicylic acid and acetic acid.

Esters are alcohol derivatives of carboxylic acids. They are named in much the same
way as salts. The alcohol part is named first, followed by the name of the acid modified
to end in -ate. The -ic ending of the organic acid name is replaced by the ending -ate.
Thus, in the IUPAC System, ethanoic acid becomes ethanoate. In the common names,
acetic acid become acetate. To name an ester, it is necessary to recognize the portion
of the ester molecule that comes from the acid and the portion that comes from the
alcohol. In the general formula for an ester, the RC=O comes from the acid, and the
R’O comes from the alcohol:

The R’ in R’O is named first, followed by the name of the acid, modified by replacing -
ic acid with -ate. The ester derived from ethyl alcohol and acetic acid is called ethyl
acetate or ethyl ethanoate. Consider the ester formed from CH3CH2COOH and CH3OH:
 Table 5.2 IUPAC Name , Common Name, and Odors of Selected Esters

Formula IUPAC Name Common Odors or

Name Flavor
O CH3 Isopentyl ethanoate Isoamyl Banana,
║ acetate pear
CH3-C-O-CH2-CH2-CH-CH3

O Ethyl butanoate Ethyl Pineapple

║ butyrate
CH3CH2CH2-C-OCH2CH3

O Isobutyl methanoate Isobutyl Raspberry

║ formate
HC- O -CH2CHCH3

CH3
O Octyl ethanoate Octyl Orange
║ acetate
CH3C-OCH2(CH2)6CH3
2-hydroxymethylbenzoate Methyl wintergreen
O salicylate
║
C-OCH3

OH

5.8 PHYSICAL PROPERTIES OF ESTERS

• low- and intermediate-molar-mass esters (above 10 carbons) are liquids with
characteristic (usually fragrant or fruity) odors
• are generally good solvents for organic substances
• with relatively low molar masses are volatile
• high-molar-masses esters (16 or more carbons) are waxes and are obtained
from various plants

5.9 CHEMICAL PROPERTIES OF ESTERS

• Acid hydrolysis

Ester + water acid + alcohol

• Alkaline Hydrolysis (Saponification)

• Saponification – the hydrolysis of an ester by a strong base to produce an
alcohol and a salt (or soap if the salt formed is from a high molar- mass acid)

Ester + NaOH salt + alcohol

5.10 SOAP and SYNTHETIC DETERGENT

Soaps
• Soaps are potassium or sodium salts of a carboxylic acid having a long aliphatic
chain attached to it.
• They are surfactants (compounds that reduce the surface tension between a
liquid and another substance) and therefore help in the emulsification of oils in
water.
• Soaps are generally prepared via the saponification of fats and oils.
• The carboxylate end of the soap molecule is hydrophilic whereas the
hydrocarbon tail is hydrophobic.
Detergents
• Detergents are the potassium or sodium salts of a long alkyl chain ending with
a sulfonate group.
• They are soluble in hard water.
• This solubility is attributed to the fact that the sulfonate group does not attach
itself to the ions present in hard water.
• Commonly, anionic detergents such as alkyl benzene sulfonates are used for
domestic purposes.

DIFFERENCE BETWEEN SOAP AND DETERGENT

The key differences between soaps and detergents are tabulated below.

Difference Between Soap and Detergent

Soaps Detergents
Consist of a ‘-COONa’ group attached Consist of a ‘-SO3Na’ group attached to
to a fatty acid having a long alkyl chain. a long alkyl chain.
They are not effective in hard water They do not lose their effectiveness in
and saline water hard water and saline water.
Soaps are completely biodegradable Detergents containing a branched
hydrocarbon chain are non-
biodegradable
They have a tendency to form scum in These compounds do not form scum.
a hard water environment.
They are derived from natural sources Detergents are synthetic derivatives.
such as vegetable oils and animal fats.
Soaps are environment-friendly These compounds can form a thick
products since they are biodegradable. foam that causes the death of aquatic
life.
Examples of soaps: sodium palmitate Examples of detergents: deoxycholic
and sodium stearate. acid and sodium lauryl sulfate.
PREPARATION OF SOAP
The most commonly used soap making process is the saponification of oils and fats.
This process involves heating oils and fats reacting them with a liquid alkali to produce
soap plus water plus glycerine.

Saponification

The other soap making process is with the neutralization of fatty acids with an alkali.
Oils and fats are hydrolyzed with high-pressure steam to yield glycerine and crude
fatty acids.

The fatty acids are later purified by the method of distillation and neutralized with an
alkali to produce water and soap.

How do Soaps and Detergents Clean out Dirt?

Cleaning a soiled surface is a four-step process. In the first step, the surface to be
cleaned is made wet with water. In the second step, soap or detergent is applied to
the surface to be absorbed.
Soaps and detergents are also called surface-active agents, or surfactants. Surface
active molecules present in soaps and detergents dissolve in water. This solution
serves to loosen surface tension or the force that holds together molecules on a
surface or on cloth. When this happens, it helps water to spread easily over a surface
or soak into clothes.
In the third step, when clothes are rubbed together, either by hand or in a washing
machine, dirt particles are broken up as surface-active molecules work to separate
the dirt from clothes and deposit them in the water. In the fourth and final step of
the cleaning process, the separated dirt is prevented from going and re-depositing
on the surface of clean clothes. Dirt particles are coated with soap and detergent
molecules. This keeps them suspended in water until the dirt is washed away with
rinsing.
https://byjus.com/chemistry/difference-between-soap-and-detergent/
 Self
Assessment
Assessment 5.1
Carboxylic acids & Esters

Name:_________________________________ Score:________
Course, Year & Section:____________________ Date:________

Give what is ask in each of the following.

__________1. Contains a carboxyl group , - C –OH or - COOH , - CO2H.

__________2. The first member of the carboxylic acid series.

CLASSIFICATION OF CARBOXYLIC ACID

3.________________________
4.________________________
5.________________________
6.________________________
7.________________________
___________8. The parent compound of carboxylic acid.
___________9. It is found in various plants, including spinach, cabbage, and
rhubarb; use as bleaching straw and leather and removing rust and
stains and are poisonous
___________10. It is made synthetically, but was originally prepared from malic
acid, which is commonly found in apples and many fruit juices;
major compounds used in the manufacture of the class of drugs
known as barbiturates
___________11. It is widely distributed in plant and animal tissue, especially in citrus
fruits.
____________12. It is found in sour milk, sauerkraut, and dill pickles; contain of
both a carboxylic acid and an alcohol; end product when our
muscles use glucose for energy in the absence of oxygen, a process
called glycolysis.
____________13. It functions as analgesic (pain reliever) and as antipyretics (fever
reducers)
____________14. It is an organic compound formed by the reaction of an acid with
an alcohol or a phenol with general formula, RCOOR’.
____________15. Refers to the hydrolysis of an ester by a strong base to
produce an alcohol and a salt (or soap if the salt formed is from a
high molar- mass acid).
 Activity

Activity 5.1
Carboxylic acids and esters

Name:___________________________ Rating:___________
Course, Year & Section:_____________ Date:_____________

I. Objective:
1. To be able to name and write structure of carboxylic acid and ester.

II.Name the following compounds.

A. Carboxylic acid

1. CH3-CH2-COOH

2. CH3-CH2-CH-COOH

CH3

CH3

3. CH3-CH2-CH-CH-CH2-COOH

CH3

B. Esters

O
║
1. CH3-C-OCH2CH3

O
║
2. CH3-CH2-C-OCH3

O
║
3. CH3-CH2-C-OCH2CH2CH3
III. Draw the following compound

A. Carboxylic acid
1. Propanoic acid
2. 2-methylbutanoic acid
3. 2,2-dimethylpentanoic acid

B. Esters
1. Methylpropanoate
2. Ethylethanoate
3. Ethylpropanoate

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“Whoever neglects discipline comes to poverty and disgrace,

But the one accepting correction will be glorified.”
Proverbs 13:18