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CA R BOX YL IC A C I D

A. DEFINITION AND STRUCTURE


Carboxylic acids are organic compounds which contain carboxyl
functional group (-COOH). A carboxyl functional group is
composed of a hydroxyl group bonded to a carbonyl carbon atom.
The carboxyl functional group is written as:

O
C CnH2nO2
OH
O O O
H C or R C or Ar C
OH OH OH
Based on number of –COOH groups carboxylic acids are classification as:
NOMENCLATURE OF CARBOXYLIC ACIDS
1. Common System
• History name
• Alkyl acetic acid (derivate of acetic acid)
• Alkane carbocylic acid

2. IUPAC System
• Alkanoic acid (1 carboxyl group)
COMPARATION IUPAC AND COMMON NAME
Formula IUPAC Common Historical Name
alkan -oic acid prefix – ic acid Source

HCOOH Methanoic acid Formic acid Latin: formica

CH3COOH Ethanoic acid Acetic acid Latin: acetum

CH3CH2COOH Propanoic acid Propionic acid Latin: protospion

CH3(CH2)2COOH Butanoic acid Butyric acid Latin: butyrum

CH3(CH2)3COOH Pentanoic acid Valeric acid Latin: valere

CH3(CH2)4COOH Hexanoic acid Caproic acid Latin: caper

CH3(CH2)5COOH Heptanoic acid Enantic acid Yunani: oenanthe


SALT OF CARBOXYCLIC ACIDS

Salt of carboxylic acids are named by


replacing the ending –ic acid with –
ate. This applies to common as well
as IUPAC Name

O C: Sodium acetate
I: Sodium ethanoate

CH3-C-ONa
EXAMPLE :

5 4 3 2 1
CH3-CH-CH2-CH2-COOH
CH3
IUPAC NAME: 4-methylpentanoic acid

Common names:
• γ -methylvaleric acid
• 2-methylpropyl acetic acid
• 3-methylbutane carboxylic acid
Isomers
Carboxylic acids can exist as chain isomer
and functional isomers with esters

C3H6O2
PHYSICAL PROPERTIES
Phase : • Low molecular weight are liquids and have sharp or
unpleasant odors.
• Larger molecular weight that have 10 or more carbons
are waxlike solids and have a little or no odor.
• Aromatic acids, as well as dicarboxylic acids, are
odorless, crystalline solids at room temperature.
: Carboxylic acids have higher boiling point than aldehydes,
Boiling
ketones, alcohols or ethers. carboxylic acids form strong
point hydrogen bonds among themselves, to water, and to other
molecules.

Alkanes < ethers < aldehydes < ketones < alcohols < carboxylic acids
E. CHEMICAL PROPERTIES
1. Salt formation with hydroxides, carbonates, and bicarbonates

The acids can be regenerated by treating these salts with dilute HCl or
H2SO4.
O O
H3C C ONa + HCl H3C C OH
Sodium acetate Acetic acid
2. Convertion Into Functional Derivates

a. Formation of acid halides/ acyl halides


Carboxylic acids react with phosphorus halides (PCl5 or PCl3) or thionyl chloride (SOCl2) to
form acid halides.
b. Formation of amides
Carboxylic acids react with ammonia to form salts, which on heating give amides.

O O O
H 3C C OH + NH3 H 3C C ONH 4 H 3C C NH 2
-H2O
Amm. acetate Acetamide
c. Formation of esters
Carboxylic acids react with alcohols in the presence of an acid catalyst (Conc. H2SO4)
to form esters.

O O
H+
H 3C C OH + H-OC2H5 H 3C C OC2H5 + H2O
Acetic acid Ethanol Ethyl acetate

Memorise:
The reaction is reversible and and is called esterification
The equilibrium can be shifted to the right by using excess of alcohol
or by removal of water by distillation
d. Formation of anhydrides
Carboxylic acids undergo dehydration with phosphorus pentoxide (P2O5)
to form acid anhydride

O O P2O5 O O
H 3C C OH + H-O C CH3 H 3C C O C CH3 + H2O
Acetic acid Acetic acid Acetic anhydride

3. Reduction with lithium aluminium hydride


Primary alcohols are formed

O
LiAlH4
H 3C C OH CH3CH2OH
Acetic acid Ether Ethanol
F. PREPARATION OF CARBOXYLIC ACID

1. Oxydation of aldehydes

Aldehydes undergo oxidation with acidic K2Cr2O7


or KMnO4 to give carboxylic acids.
O + O
K2Cr2O7/H
H3C C H H3C C OH
Acetaldehyde Acetic acid
2. Oxydation of primary alcohols.

Primary alcohols undergo oxidation with acidic


K2Cr2O7 or KMnO4 to form carboxylic acids. The
alcohol is first oxidized to an aldehyde, and then to a
carboxylic acid.

K2Cr2O7 K2Cr2O7
CH3CH2OH CH3CHO CH3COOH
H2SO4 H2SO4
Ethyl alcohol Acetaldehyde Acetic acid
3. Hydrolysis of cyanides

Alkyl cyanides on acid-hydrolysis form


carboxylic acids. The alkyl cyanides (RCN)
are prepared by treating alkyl halides with
sodium cyanide.
:

H2O O
NaCN
CH3Br H3C C N H3C C OH + NH3
-NaBr H+
Methyl Methyl Acetic acid
bromide cyanide
4. Carbonation of Grignard reagents

Grignard reagent (RMgX) react with CO2 to give addition compound. These
on acidification yield carboxylic acids.

O O O
H2O/H+
R-MgX + C O R C O MgX R C OH + Mg(OH)X

Not isolated

Memorizse:
a. RX + MgRMgX
b. The acid formed by this method contains one more carbon than the Grignard reagent
5. Hydrolysis of esters

O O
H3C C OC2H5 + NaOH H3C C -ONa+ + C2H5OH
Ethyl acetate Sodium acetate Ethanol

O O
H3C C -ONa+ + HCl H3C C OH + NaCl
THE USES OF CARBOXYLIC ACID
Countries such as Austria and Switzerland.
These countries, which fight bitter winters
and very dangerous roads, are now using
formates, which are the salts that are
derived from formic acid (increase the
gripping ability).
• Methanoic acid (formic acid)
– Used in the production of leather.
– Used in textile and rubber industries.
– Because of its natural antibacterial
properties is used in antibacterial
preservative and pesticide and food
additives-
THE USES OF CARBOXYLIC ACID
• Manufacturing of soaps need higher fatty acids. Soaps are generally sodium or
potassium salts of higher fatty acids such as stearic acid.
• Food industry uses many organic acids for the production of soft drinks, food
products etc. For example, acetic acid is used in making vinegar. Sodium salts of
organic acids find application in preservatives.
• In pharmaceutical industry organic acids are used in many drugs such as aspirin,
phenacetin etc.
• Acetic acids are often used as a coagulant in the manufacturing of rubber.
• Organic acids find huge application in making dye stuff, perfumes and rayon