Nitrous acid is used to make diazonium salts from amines. The nitrite and the acid form nitrous acid which reacts with the amine. Nitrous acid (also known as nitric(III) acid) has the formula HNO 2. It is sometimes written as HONO to show the way it is joined up. This migration results in an expansion of the ring.

That's because any acid we add will react with the amine, so the strongest acid we can have in the reaction is the conjugate acid of the amine.

Nitrous acid reactions of 1º-aryl amines generate relatively stable diazonium species that serve as intermediates for a variety of aromatic substitution reactions. Nitrosation of Amines. Nitrous acid (molecular formula H N O 2) is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite (NO − 2) salts. Primary amines react with nitrous acid to yield a diazonium salt, which is highly unstable and degradates into a carbocation that is capable of reaction … Nitrous acid is a weak acid and we get the following chemical reaction. The classic nitrosation mechanism usually involves nitrite, which participates the formation of nitrosating agent in the acidic solution 26−28 or in the presence of hypochlorite (HOCl), 29,30 carbonyl compounds, 15,31,32 or sunlight. Diazonium cations may be described by resonance contributors, as in the bracketed formulas shown below. The Action of Nitrous Acid on Aliphatic Amines Nature 188, 1086-1088 (1960) as reference 472 to support the above information. So, if you consider whether amines will react with nitrous acid, the answer is YES! However, the product with a secondary amine is a powerful carcinogen, and so this reaction is no longer carried out at this level. Examines the history of investigation into the reaction of tertiary amines with nitrous acid as an example of the inherently conservative nature of science and resistance to new concepts. This displacement can occur via a rearrangement (path A), in which one of the sigma bonds adjacent to the diazo group migrates. Diazotization reaction mechanism generally involves the usage of nitrous acid and another acid in the treatment of aromatic amines in order to yield the diazonium salt. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous.
Nevertheless the denitrosation reaction can be studied if steps are taken to remove the nitrous acid at such a rate that it is much faster than the reverse reaction of Eq. Reaction mechanism. The left-hand contributor is dominant because it has greater bonding. The equilibrium position lies towards right because nitrous acid is a weak acid. Salt formation is instantly reversed by strong bases such as NaOH. The reaction process begins with diazotization of the amine by nitrous acid. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes
Reaction with nitrous acid. Nitrous acid is unstable and must be prepared in the reaction solution by mixing sodium nitrite with acid. Amine - Amine - Reactions of amines: Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. The reaction between amines and nitrous acid was used in the past as a very neat way of distinguishing between primary, secondary and tertiary amines. Nitrous acid reactions of 1º-aryl amines generate relatively stable diazonium species that serve as intermediates for a variety of aromatic substitution reactions. (82). Diazotization Mechanism, Sandmeyer Reaction, Arenediazonium Salts, Diazo Coupling, Organic Chemistry - Duration: 31:29. Some of the most important reactions of amines are brought about by nitrous acid \(\left( \ce{HONO} \right)\). In the case of its reaction with phenylamine, the phenylamine is first dissolved in hydrochloric acid, and then a solution of sodium or potassium nitrite is added.

The diazonium group is a good leaving group, forming nitrogen gas when displaced from the organic structure.

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