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Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained.
In the related Hammick reaction, uncatalyzed decarboxylation of a picolinic acid gives a stable carbene that attacks a carbonyl electrophile. Oxidative decarboxylations are generally radical reactions. These include the Kolbe electrolysis and Hunsdiecker-Kochi reactions. The Barton decarboxylation is an unusual radical reductive decarboxylation.
The Koch reaction is an organic reaction for the synthesis of tertiary carboxylic acids from alcohols or alkenes and carbon monoxide. Some commonly industrially produced Koch acids include pivalic acid , 2,2-dimethylbutyric acid and 2,2-dimethylpentanoic acid. [ 1 ]
It is the precursor to nitric acid, which is the source for most N-substituted aromatic compounds. Amines can be formed by the reaction of ammonia with alkyl halides or, more commonly, with alcohols: CH 3 OH + NH 3 → CH 3 NH 2 + H 2 O. Its ring-opening reaction with ethylene oxide give ethanolamine, diethanolamine, and triethanolamine.
Carbamic acid is a planar molecule. [3]The H 2 N− group of carbamic acid, unlike that of most amines, cannot be protonated to an ammonium group H 3 N + −.The zwitterionic form H 3 N + −COO − is very unstable and promptly decomposes into ammonia and carbon dioxide, [6] yet there is a report of its detection in ices irradiated with high-energy protons.
Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones, the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3, which loses water in an elimination reaction to diazoiminium 5.
The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product.
The Schiff base is an electrophile which reacts in a second step in an electrophilic addition with an enol formed from a carbonyl compound containing an acidic alpha-proton. The Mannich reaction is a condensation reaction. [4]: 140 In the Mannich reaction, primary or secondary amines or ammonia react with formaldehyde to form a Schiff base ...