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These reactions proceed via the intermediacy of amides. The intramolecular reaction of a carboxylic acid with an amide is far faster than the intermolecular reaction, which is rarely observed. They may also be produced via the oxidation of amides, particularly when starting from lactams. [6] R(CO)NHCH 2 R' + 2 [O] → R(CO)N(CO)R' + H 2 O
The core −C(=O)−(N) of amides is called the amide group (specifically, carboxamide group). In the usual nomenclature, one adds the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH 3 CONH 2). IUPAC recommends ethanamide, but this and related formal names are rarely ...
Peptide amidase (Pam), [1] which catalyses the hydrolysis of the C-terminal amide bond of peptides. Fatty acid amide hydrolases, [2] which hydrolyse fatty acid amid substrates (e.g. cannabinoid anandamide and sleep-inducing oleamide), thereby controlling the level and duration of signalling induced by this diverse class of lipid transmitters.
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...
The amide derivatives that are obtained by Beckmann rearrangement can be transformed into a carboxylic acid by means of hydrolysis (base or acid catalyzed). Beckmann rearrangement is used for the industrial synthesis of caprolactam (see applications below).
Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. [11] Alternatively the workup may be via the Ing–Manske procedure, involving reaction with hydrazine. This method produces a precipitate of phthalhydrazide (C 6 H 4 (CO) 2 N 2 H 2) along with the primary amine: C 6 H 4 (CO) 2 NR + N 2 H 4 → C 6 H 4 (CO) 2 N 2 ...
The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1] [2] [3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.