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1° Amines to Diazonium ...
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.\r\n \r\n Figure 1. The mechanism of the diazotization reaction of primary amines.\r\n As illustrated in Figure 1, in the mechanism of the reaction, a primary amine attacks as the nucleophile on the nitrosonium ion. The subsequent deprotonation yields an N-nitrosamine. Next, the N-nitrosamine readily undergoes keto-enol tautomerism to give a diazotic acid. Protonation of the diazotic acid followed by water loss results in the formation of diazonium ions. The aliphatic diazonium ions formed are extremely unstable and readily decompose to form a carbocation by releasing molecular nitrogen even at 0 °C, which is a good and stable leaving group.\r\n
Material Proyectable
material_proyectable Rebiun36496947 https://catalogo.rebiun.org/rebiun/record/Rebiun36496947 m o c vz czazuu cr cnannnuuuuu 230725s2022 mau002 o vleng d 12864 JoVE UCEU on1391119492 12864 MyJoVE Corporation MAJOV eng rda pn MAJOV eng eng 1° Amines to Diazonium or Aryldiazonium Salts Diazotization with NaNO2 Mechanism Cambridge JoVE 2022 Cambridge Cambridge JoVE 1 online resource (1 video file (1 min., 37 sec.)) sound, color 1 online resource (1 video file (1 min., 37 sec.)) 000137 Two-dimensional Moving Image tdi rdacontent computer c rdamedia online resource cr rdacarrier digital rdatr video file rdaft Core: Organic Chemistry. Amines 19.26 2769-4496 Presented by MyJoVE Corporation Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.\r\n \r\n Figure 1. The mechanism of the diazotization reaction of primary amines.\r\n As illustrated in Figure 1, in the mechanism of the reaction, a primary amine attacks as the nucleophile on the nitrosonium ion. The subsequent deprotonation yields an N-nitrosamine. Next, the N-nitrosamine readily undergoes keto-enol tautomerism to give a diazotic acid. Protonation of the diazotic acid followed by water loss results in the formation of diazonium ions. The aliphatic diazonium ions formed are extremely unstable and readily decompose to form a carbocation by releasing molecular nitrogen even at 0 °C, which is a good and stable leaving group.\r\n Presented in English; subtitles in English Instructional and Educational Work MyJoVE Corporation production company publisher Core. Organic Chemistry. Amines 19.26. 2769-4496