Blog / Carboxylic Acids Important Reactions

Carboxylic Acids: Important Reactions

Written by Sabina Cabrera on Mar 27, 2020

Due to the reactive nature of both the carbonyl and hydroxyl group on the carboxylic acid, they are most useful with nucleophilic attacks, particularly with amines and esters; anhydride formation and reduction of the functional groups within the carboxylic acids are possible.

1.Carboxyl group reactions

Due to the electron-poor carbon in the carboxylic acid, carboxylic acids can be functionalized via nucleophilic addition. In this case, the hydroxyl (-OH) in the carboxylic acid leaves and is replaced by the nucleophile (R) attacking the carbon, which can be represented by (R-C=O).

In certain circumstances, the oxygen in the hydroxyl can act as the nucleophile and attack the carbon on a different carboxylic acid,

a)Amides, esters, anhydride formation

Amides are formed via the addition of a carboxylic acid and a primary amine using DCC as an activating agent.

Esters are formed by the addition of carboxylic acid and an alcohol under the presence of a strong acid. The most common reaction for this is Fischer Esterification.

In the presence of a base, acid anhydrides are formed by the addition of a carboxylic acid and an acid chloride.

b)Reduction

Carboxylic acids can have the carbonyl oxygen reduced to two hydrogens by a reducing agent such as LiAlH4.

c)Decarboxylation

Decarboxylation is the removal of carbon dioxide (CO2) from a carboxylic acid group. In the case of a carboxylic acid compound, such as (R-COOH), decarboxylation would produce (-R-H) and (O=C=O).

Key Takeaways:

  • Carboxylic acids can be highly reactive and can undergo nucleophilic addition.
  • Esters, amides, and acid anhydrides can be derived from carboxylic acids.


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