Lesson Nine

Carboxylic acid and derivatives

Carboxylic acids are a class of organic compounds characterized by

carboxyl group.

O
C OH    (Also written –CO2H  or –COOH)

The general formula for carboxylic acid is RCOOH.

Nomenclature

Carboxylic acids   :-

(i)  In IUPAC system of nomenclature

carboxylic acid is named by
replacing the ending e of an alkane
name with oic acid , e. g.

O   COOH

H OH CH3 CH2 COOH

methanoic propanoic acid phenyl

acid methanoic acid

(ii) For substituted acid, the carbonyl

carbon is always the C-1 carbon of
carboxylic acid.

H3CO O

CH3 CH2 CH C OH
4 3 2 1

2-methoxy butanoic acid

(ii) Carboxylic acid in which

carboxylic group is attached to a
cyclic compound can be named by
adding carboxylic acid to the name
of the cyclic compound.

COOH COOH

HOOC COOH
1,3,5-benzene tricarboxylic acid cyclopentane carboxylic acid

Acyl halides   :-

          These are named by using the acid name and

replacing ic by yl halides.

H3C C Cl

Ethanoyl chloride

Acid anhydrides   :-

          For symmetrical anhydride we add in the end of the name

of acid anhydride . But if it’s unsymmetrical is named by starting
the names of both acids in alphabetical order, followed by
anhydride .

O O O O

H3C C O C CH3 H3C C O C CH2 CH3

Ethanoic anhydride ethanoic propanoic anhydride

Esters:-

In this the name of the group attached to carboxylic

oxygen is stated first. This is followed by the name of the acid
with ic acid repalced by ate .

O O

H3C C O CH2 CH3 C O CH2 CH3

Ethyl ethanoate ethyl benzoate

 

Amides:-

Primary amides are named by using acid name replacing

oic by amide , if there is a substituent bonded to nitrogen the
name of the substituent is named first followed by the name of
the amide.

O
CONH2
NH C CH2 CH3

Phenyl methanamide N-cyclohexyl propanamide

Dicarboxylic acids: 

Dicarboxylic acids are compounds that have two carboxyl groups. To

memorize these acids, note their first letters (o, m, s, g, a, p) fit the expression "
Oh My Such Good Apple Pie".

COOH COOH H2C COOH

H2C
COOH COOH H2C COOH

    Oxalic acid                        Malonic acid                                   Succinic

acid   

H2C COOH H2C CH2 COOH

H2C HOOC (CH2)5 COOH
H2C COOH H2C CH2 COOH

Glutamic acid                         Adepic acid                       

Pimelic acid
 

Phthalic acid is an aromatic dibasic acids COOH

 
COOH
 

The unsaturated dicarboxylic acids maleic and fumaric acid are geometric
isomers

HOOC COOH HOOC H

H H H COOH

Maleic acid                             Fumaric acid

Polyfunctional Carboxylic acids:

Poly functional carboxylic acids are carboxylic acids acid that contain
other functional groups as well. Latic acid is a hydroxyl acid.

OH
CH
H3 C COOH
Lactic acid

When lactose (milk sugar) is fermented by the bacteria, lactic acid is

produced. It is responsible for the sour taste of sour milk. Other hydroxy acids
are citric, tartaric and salicylic acids.

 
H2C COOH H COOH
HO C COOH
HO C COOH
HO C COOH OH
H2C COOH H

Citric acid                                      Tartaric acid        

Salicylic acid

Here are some examples of carboxylic acids with functional groups other than
hydroxyl groups:

O
Cl NH2
C
H3C COOH H2C COOH H2C COOH

Pyruvic acid Chloroacetic acid Glycine