Grade 12

Grade 12Aldehydes, 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.

C=O Oh R

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.


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