Gattermann Reaction – Mechanism, Steps and Applications

What is the Gattermann Reaction?

The Gattermann Reaction is a synthetic organic reaction used to produce aldehydes and ketones from carboxylic acids. The reaction uses a palladium catalyst to convert the carboxylic acid to an aldehyde or ketone. The reaction is named for the chemist Heinrich Gattermann, who first developed the reaction in 1898.

Gattermann Reaction can be written as Follows

• In the presence of a base, an alkyl halide and an aryl Grignard reagent react to form an alkyl aryl ether.
• The Grignard reagent attacks the alkyl halide to form a new carbon-carbon bond. The halide ion then leaves, and the aryl group moves to form a new carbon-carbon bond with the Grignard reagent.
• The reaction is named after the German chemist Louis Gattermann, who first reported it in 1901.

How is Diazonium Salt Formed?

A diazonium salt is a salt of a diazonium compound, which is a nitrogen-containing organic compound. The salt is formed when the diazonium compound reacts with a metal or a mineral acid.

Diazotization of Aniline

The diazotization of aniline is a chemical reaction in which aniline is converted into aniline hydrochloride. The reaction is performed by adding a solution of sodium nitrite to a solution of aniline. The sodium nitrite converts the aniline into aniline nitrate, which is then converted into aniline hydrochloride by the addition of hydrochloric acid.

Synthesis of Aromatic Aldehyde by Gattermann Reaction

• Benzaldehyde can be synthesized from toluene by the Gattermann reaction. In this reaction, toluene is converted to benzoic acid, which is then converted to benzaldehyde.
• The Gattermann reaction proceeds through a series of steps in which a carboxylic acid is converted to an aldehyde. The reaction begins with the conversion of toluene to benzoic acid. Benzoic acid is then converted to benzaldehyde by the removal of a water molecule.
• The Gattermann reaction is used to produce a number of aromatic aldehydes, including benzaldehyde, cinnamaldehyde, and vanillin.

Gattermann Reaction Mechanism

• The Gattermann reaction mechanism is the proposed mechanism for the organic reaction of aldehydes and ketones with ammonia to form amides. The reaction is named for the German chemist Friedrich Gattermann, who first reported it in 1894.
• The mechanism involves the formation of an amide intermediate, which is then protonated to form the amide product. The mechanism is shown below.
• The first step in the reaction is the formation of the amide intermediate. This is done by the addition of ammonia to the aldehyde or ketone. The nitrogen of the ammonia molecule attacks the carbon of the aldehyde or ketone, and the hydrogen of the ammonia molecule attacks the oxygen of the carbonyl group. This forms an amide bond between the nitrogen and carbon.
• The next step is the protonation of the amide intermediate. This is done by the addition of a proton to the nitrogen atom. This proton comes from a hydrogen atom of the solvent, and the protonated amide intermediate is then called an amide proton.
• The amide proton then reacts with the remaining oxygen atom of the carbonyl group to form the amide product. This reaction is called an elimination reaction, and it is done by the loss of a water molecule.

Applications of Gattermann Reaction

• The Gattermann reaction is used to synthesize indole derivatives from α-bromo ketones.
• The Gattermann reaction is a chemical synthesis reaction used to produce ketones from aldehydes and alcohols.
• The reaction is performed in the presence of a base, usually sodium hydroxide, and produces a ketone and a salt.
• The Gattermann reaction is used in the production of synthetic flavors and fragrances, and has also been used in the production of pharmaceuticals.

The Formation of Diazonium Salt

• The formation of a diazonium salt is a two-step process. The first step is the formation of the diazonium ion from an aromatic compound and a nitrogen gas. The second step is the addition of the diazonium ion to an aldehyde or ketone.
• The formation of the diazonium ion is shown below. In this reaction, an aromatic compound and a nitrogen gas react to form the diazonium ion.
• The addition of the diazonium ion to an aldehyde or ketone is shown below. In this reaction, the diazonium ion is added to an aldehyde or ketone to form a diazonium salt.

The Mechanism of Gattermann Reaction

• The Gattermann reaction is a chemical reaction that produces a substituted benzene compound from two other benzene compounds.
• The reaction is named for its inventor, German chemist Friedrich Gattermann.
• The reaction mechanism is not fully understood, but it is believed to involve the formation of a benzene ring from two benzene molecules.