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Nomenclature &
Preparation
Carboxylic Acids
LECTURE 1
Dr. Monica Bedi
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Nomenclature &
Preparation
Carboxylic Acids
LECTURE 1
Carboxylic acids
Carboxylic acids
Carboxylic acids
Carboxylic acids
i. Carboxylic acids :
Organic compounds containing carboxyl groups
Called carboxylic acids. The carboxyl group is made up
Carbonyl, >C = O and hydroxyl, -OH group, hence, its name is
carboxyl group
Nomenclature
In IUPAC system, the monocarboxylic acids are called alkanoic
acids
O
OH
CH3COOH
O
OH
HCOOH
H
OH
O
CH3CH2COOH
OH
Br
CH3CH2CHCOOH
O
Br
OH
O
CH3CHCOOH
CH3
OH
CH3CH2CH2COOH
O
CH3(CH2)3CHCOOH
O
OH
HOOC - COOH
I. by oxidation of primary alcohols :
General methods of preparation
R - CH2OH +2[O] R-COOH + H2O
CH3CH2OH + 2[O]
kmnO4/H+
CH3COOH + H2O
II. by oxidation of aldehydes :
Ethyl alcohol
Acetic acid
R - CHO + [O] R-COOH
CH3CHO + [O] CH3COOH
Acetaldehyde Acetic acid
From Alkyl benzenes :
The alkyl side chain oxidised to - COOH group irrespective
Of the size of the chain
Alkyl benzenes
From Alkyl benzenes :
The alkyl side chain oxidised to - COOH group irrespective
Of the size of the chain
Alkyl benzenes
Nitriles and amides
O
II
R - CN
H+ or -OH
RCOOH
R - C-NH2
H2O
H+ or -OH
CH3COOH + NH3
CH3CONH2
H+ or -OH
Ethanamide Ethanoic acid
CONH2
COOH
Benzamide Benzoic acid
H3O+
+ NH3
Grignard reagents
R-Mg-X + O = C =O H3O+
Dry ether
R-C
RCOOH
MgX+
Bring about the following transformations
Br
OH
O
II
CH2CH3
KmnO4
KOH, heat
I. Methanal
II. 2-Methylpentanal
III. Benzaldehyde
IV. Benzophenone
V. Cyclohexanone
VI. 1-Phenylpropanone
VII. Butan-1-ol
VIII.2,2-Dimethylbutanal
Which of the following compounds would undergo aldol condensation, which
the Cannizzaro reaction and which neither? Write the structures of the
expected products of aldol condensation and Cannizzaro reaction.
I. Methanal
II. 2-Methylpentanal
III. Benzaldehyde
IV. Benzophenone
V. Cyclohexanone
VI. 1-Phenylpropanone
VII. Butan-1-ol
VIII.2,2-Dimethylbutanal
Write structural formulas and names if four possible aldol condensation
products from propanal and butanal. In each case, indicate which aldehyde
acts as nucleophile and which as electrophile
An organic compound with molecular formula C9H10O forms 2,4- DNP
Derivative, reduces tollen’s reagent and undergoes cannizzaro reaction. On
vigorous oxidation, it gives 1,2- benzenedicarboxylic acid, identify compound.
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