Grade 12 → Aldehydes, ketones and carboxylic acids ↓
Preparation and Properties of Carboxylic Acids
Carboxylic acids are an important group of organic compounds known for their widespread presence in nature and industrial applications. Carboxylic acids contain -COOH
functional group. In this article, we will explore how to prepare carboxylic acids and examine their properties.
Preparation of carboxylic acids
1. Oxidation of alcohols and aldehydes
Carboxylic acids can be prepared by oxidizing primary alcohols or aldehydes. This reaction proceeds via the transformation of the alcohol or aldehyde into an acid.
RCH2OH → RCHO → RCOOH
Here, RCH2OH
is a primary alcohol, which is oxidized to the aldehyde RCHO
, and further oxidation gives the carboxylic acid RCOOH
.
2. Oxidative fragmentation of alkenes
Alkenes can be converted into carboxylic acids using oxidative cleavage. The double bond in the alkene is broken, and carboxylic acids are formed.
RCH=CHR' + [O] → RCOOH + R'COOH
In this reaction, the alkene RCH=CHR'
is oxidised to form two carboxylic acids RCOOH
and R'COOH
.
3. Hydrolysis of nitriles
Nitriles can produce carboxylic acids by hydrolysis. This reaction is carried out under acidic or alkaline conditions.
RCN + 2H2O → RCOOH + NH3
In this reaction, nitrile RCN
reacts with water to form carboxylic acid RCOOH
and ammonia NH3
.
4. Carbonation of Grignard reagents
Grignard reagents can be used to prepare carboxylic acids by reacting with carbon dioxide.
RMgX + CO2 → RCOOMgX RCOOMMgX + H2O → RCOOH + MgX(OH)
The Grignard reagent RMgX
reacts with carbon dioxide CO2
to form carboxylate salts, which on hydrolysis give carboxylic acids RCOOH
.
Properties of carboxylic acids
1. Physical properties
Carboxylic acids are generally polar compounds, as they can form hydrogen bonds with water and themselves, causing them to have higher boiling points than other organic compounds of similar molecular weight. They are often soluble in water due to the formation of hydrogen bonds.
For example, acetic acid, commonly known as carboxylic acid, is soluble in water.
2. Acidity of carboxylic acids
Carboxylic acids are acidic because they can donate a proton H+
from -COOH
group to form the carboxylate ion RCOO -
.
RCOOH ⇌ RCOO− + H+
This equation shows the reversible dissociation of carboxylic acid into carboxylate ion and hydrogen ion. Due to the ability to donate protons, these compounds are acidic and have a sour taste.
3. Chemical reactions of carboxylic acids
3.1. Esterification
Carboxylic acids react with alcohols in the presence of an acid catalyst to form esters, a process called esterification.
RCOOH + R'OH → RCOOR' + H2O
For example, acetic acid reacts with ethanol to form ethyl acetate and water.
3.2. Deduction
Carboxylic acids can be reduced to primary alcohols using reducing agents such as lithium aluminium hydride LiAlH4
.
RCOOH + 4[H] → RCH2OH + H2O
This process involves the reduction of carboxyl group to hydroxyl group.
3.3. Decarboxylation
Decarboxylation is the process in which carboxylic acids lose a carbon dioxide molecule to form alkenes.
RCOOH → RH + CO2
For example, heating sodium salts of carboxylic acids with soda lime causes decarboxylation.
Visual representation
Let us look at the structure of carboxylic acids and their reactions.
The illustration above shows the structure of a typical carboxylic acid, where R refers to any alkyl or aryl group attached to the carboxyl group -COOH
.
Conclusion
Carboxylic acids are versatile compounds that are essential in a variety of chemical processes and everyday products. Methods for their preparation, ranging from the oxidation of alcohols to the hydrolysis of nitriles, provide numerous pathways to synthesize these acids. The properties of carboxylic acids, particularly their acidity and reactivity, make them important in both laboratory synthesis and industrial applications.
Understanding the formation and properties of carboxylic acids provides a strong foundation to delve deeper into organic chemistry and explore the wide range of derivatives and applications that arise from these basic compounds.