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Carboxylic Acids

Carboxylic acids can be synthesized through oxidation of primary alcohols and aldehydes, hydrolysis of nitriles, and Grignard reactions. They have higher boiling points than alcohols due to strong intermolecular hydrogen bonding. Aliphatic acids with 1-4 carbons are soluble in water. Carboxylic acid strength is influenced by inductive/resonance effects and intramolecular hydrogen bonding. The Hell-Volhard-Zelinsky reaction is used to prepare carboxylic acids from alkyl halides and involves a carbon-carbon bond forming reaction. Carboxylic acids undergo reactions like chlorination, esterification, reduction, decarboxylation, and the Hun

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52 views12 pages

Carboxylic Acids

Carboxylic acids can be synthesized through oxidation of primary alcohols and aldehydes, hydrolysis of nitriles, and Grignard reactions. They have higher boiling points than alcohols due to strong intermolecular hydrogen bonding. Aliphatic acids with 1-4 carbons are soluble in water. Carboxylic acid strength is influenced by inductive/resonance effects and intramolecular hydrogen bonding. The Hell-Volhard-Zelinsky reaction is used to prepare carboxylic acids from alkyl halides and involves a carbon-carbon bond forming reaction. Carboxylic acids undergo reactions like chlorination, esterification, reduction, decarboxylation, and the Hun

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xdawy2004xd
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15/03/2023

Carboxylic acids
By
Dr. Zahra Ali Kassem

Carboxylic acids

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Nomenclature
1. Trivial:

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Nomenclature
2.IUPAC

Give the IUPAC nomenclature for:

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Synthesis
1. oxidation:
a) Oxidation of primary alcohols and adehydes
e,.g.

B ) oxidation of aralkyl

Synthesis
2.Hydrolysis of nitriles:

3.Grignard:

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Physical properties

Therefore
1. Carboxylic acids have high boiling points (which
is higher than the corresponding alcohol).
2. Aliphatic acids (C1-C4) are soluble in water.

Reactions
1. Acidity:

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1. Acidity :
Acidity is affected by:
Electronic factors (induction or resonance)
Hydrogen bonding ( intramolecular )
a ) Electronic effect:
Groups having –I or –R Acidity
Groups having +I or +R Acidity

i. Aliphatic acids (mainly inductive ):


Acid pKa Acid pKa
CH₃COOH 4.8 CH₃CH₂COOH 4.8
HCOOH 3.8 CH₃= CHCOOH 4.2
ICH₂COOH 3.2 HCΞCCOOH 1.8
CICH₂COOH 2.9
FCH₂COOH 2.7
O₂NCH₂COOH 1.7
Cl₂CHOOH 1.3
Cl₃CCOOH 0.65

Acidity:

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ii. Aromatic acids


A- induction and resonance:

Acidity:
Nitrobenzoic acid ( -I and –R)

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iii. Dicarboxylic acids:

Difference in acidity between two carboxylic groups:

1. Acidity:
b) Hydrogen bonding:
e.g.1

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b) Hydrogen bonding:
e.g.2

Reactions
2- Chlorination
RCOOH + SOCl₂ → RCOCl + HCl + SO₂
3- Esterification
RCOOH + R’OH → RCOOR’ + H₂O

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Reactions
4- Reduction

Reactions
5- HellVolhard –Zelinsky

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5- HellVolhard –Zelinsky
Importance :

6- Decarboxylation

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Other Reactions
1- Hunsdieker Reaction
(free radical mechanism)

2- Reaction with amines to give amides (will be


dicussed in acid deriv.)

3- Dehydration to give anhydrides (will be discussed in


acid deriv.)

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