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For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H 2 NC 6 H 4 SO 3 H. If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. To generate the mono-substituted product, a protection with acetyl chloride is required:
2,4,6-Tribromoaniline can be prepared by treating bromine water with aniline in a solution of acetic acid or dilute hydrochloric acid: [1] By reacting bromine with aniline in water, a white precipitate immediately forms and that is 2,4,6-tribromoaniline
Sodium sulfide (or hydrogen sulfide and base). Illustrated by the selective reduction of dinitrophenol to the nitroaminophenol. [11] Tin(II) chloride [12] Titanium(III) chloride; Samarium [13] Hydroiodic acid [14] Metal hydrides are typically not used to reduce aryl nitro compounds to anilines because they tend to produce azo compounds. (See below)
Illustrative is the acetylation of aniline. First aniline is dissolved in water using one equivalent of hydrochloric acid. This solution is subsequently treated, sequentially, with acetic anhydride and aqueous sodium acetate. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion: Acetate then acts as a leaving group:
Azide salts can decompose with release of nitrogen gas. The decomposition temperatures of the alkali metal azides are: NaN 3 (275 °C), KN 3 (355 °C), RbN 3 (395 °C), and CsN 3 (390 °C). This method is used to produce ultrapure alkali metals: [4] 2 MN 3 2 M + 3 N 2. Protonation of azide salts gives toxic hydrazoic acid in the presence of ...
A 6 electron cyclization reaction with the loss of another ethanol molecule forms a quinoline (ethyl 4-oxo-4,4a-dihydroquinoline-3-carboxylate). The enol form can be represented from the keto form through keto-enol tautomerism. Protonation of the nitrogen forms ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate. Mechanism for the Gould-Jacobs reaction
In the reaction, thermal or photochemical decomposition of N-halogenated amine 1 in the presence of a strong acid (concentrated sulfuric acid or concentrated CF 3 CO 2 H) generates a nitrogen radical intermediate. The radical then abstracts an intramolecular hydrogen atom to give a cyclic amine 2 (pyrrolidine or, in some cases, piperidine).
HAT reactions are common in various redox reactions, hydrocarbon combustion, and interactions involving cytochrome P450 that contain an Fe(V)O unit. The entity removing the hydrogen atom, known as the abstractor (X•), is often a radical itself, though in some instances, it may be a species with a closed electron shell, such as chromyl chloride.