CHAPTER 4.

3
C A R B OX Y L I C AC I D
 LEARNING OUTCOME
At the end of the lesson, student should be able to:
1. Assign IUPAC names for carboxylic acid
2. Draw the structure of carboxylic acid according to IUPAC
name
3. Distinguish chemical and physical properties of carboxylic
acid
4. State the uses of carboxylic acid
 CARBOXYLIC ACID
• Contains functional group –COOH
• Organic compounds which contain the carboxyl functional group
are called as carboxylic acids.
• The name carboxyl is derived from carbonyl(C=O) and
hydroxyl(OH)
NAMING CARBOXYLIC ACID
EXAMPLE C
6
C
5
C
4
C
3
C
2
COOH
1

CH3 CH3
6 5 4 3
H3C H2C C C CH2 COOH
H H 2 1

3,4-dimethylhexanoic acid

Br

H3C C COOH
H
2-Bromopropanoic acid
 PHYSICAL PROPERTIES
• Colourless liquid at room temperature & relatively low boiling
point of 118⁰C
• Dissolve in water
• Has a characteristic ‘sour-ish’ smell
• Is a weak acid of pH 3
• Boiling points and melting point of carboxylic acids increase with
increase in molecular weight.
• Boiling points of carboxylic acids are higher than those of
alcohols of same molecular weight.
• First four members are completely soluble in water. This is due
to the ability of the carboxyl group to form hydrogen bonds with
water molecules. Carboxylic acids readily soluble in ethanol,
ether and benzene.
PREPARATION OF CARBOXYLIC ACID

1. OXIDATION OF PRIMARY ALCOHOL AND

ALDEHYDES
2. HYDROLYSIS OF ESTER
 1. OXIDATION OF PRIMARY ALCOHOL
AND ALDEHYDE
• Primary alcohols or aldehydes undergo oxidation with a mixture
of potassium dichromate and sulphuric acid to form carboxylic
acids. The alcohol is first oxidised to an aldehyde, and then to a
carboxylic acid.
 2. HYDROLYSIS OF ESTER

• When an ester is boiled with concentrated aqueous NaOH,

sodium salt of the acid is formed. This on treatment with dilute HCl
gives carboxylic acid. For example,
 CHEMICAL REACTION

1. FORMATION OF AMIDE
2. FORMATION OF ESTER
3. REDUCTION
 1. FORMATION OF AMIDE

• Carboxylic acids react with ammonia to give salts, which on

heating yields amides.

O O

CH3 C OH NH3 CH3 C ONH3

Acetic acid Ammonium acetate
-H2O

CH3 C NH2
Acetamide
 2. FORMATION OF ESTER

• Carboxylic acids react with alcohol in the presence of a strong

acid catalyst like H2SO4 or HCl to form esters. The reaction is
reversible and is called esterfication.
 3. REDUCTION

• Carboxylic acids undergo reduction with lithium aluminium

hydroxide to give primary alcohols.

LiAlH4
CH3 C OH CH3 CH2 OH
Ether
Acetic acid Ethanol
 USES OF CARBOXYLIC ACID
• Carboxylic acids are also important in manufacture of greases,
crayons, and plastics.
• Higher fatty acids are used in the manufacture of soaps.
• Organic acids are used in foods, cold drinks, etc. For example,
acetic acid is used as vinegar.
• Organic acids are used for the preparation of many drugs such
as aspirin, phenacetin etc.
• Acetic acid is used as coagulant in the manufacture of rubber.
• Acetic acid is also used in the manufacture of various dye stuffs,
perfumes and rayon.