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The reaction, which involves simultaneous nitration and oxidation, was first reported by the German chemists Richard Wolffenstein and Oskar Böters in 1906. [4] The Wolffenstein-Boters reaction. According to one series of studies the mercury nitrate first takes benzene to the corresponding nitroso compound and through the diazonium salt to the ...
In the case of nitration of benzene, the reaction is conducted at a warm temperature, not exceeding 50 °C. [6] The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring: Alternative mechanisms have also been proposed, including one involving single electron transfer (SET). [7 ...
Many other electrophilic reactions of benzene are conducted, although on a much smaller scale; they are valuable routes to key intermediates. The nitration of benzene is achieved via the action of the nitronium ion as the electrophile. The sulfonation with fuming sulfuric acid gives benzenesulfonic acid.
This reaction is similar to nucleophilic aliphatic substitution where the reactant is a nucleophile rather than an electrophile. The four possible electrophilic aliphatic substitution reaction mechanisms are S E 1, S E 2(front), S E 2(back) and S E i (Substitution Electrophilic), which are also similar to the nucleophile counterparts S N 1 and ...
In nitration, benzene reacts with nitronium ions (NO 2 +), which is a strong electrophile produced by combining sulfuric and nitric acids. Nitrobenzene is the precursor to aniline . Chlorination is achieved with chlorine to give chlorobenzene in the presence of a Lewis acid catalyst such as aluminium tri-chloride.
The nitration product produced on the largest scale, by far, is nitrobenzene. Many explosives are produced by nitration including trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). [3] Another but more specialized method for making aryl–NO 2 group starts from halogenated phenols, is the Zinke nitration.
The mechanism of the Zincke reaction This mechanism can be referred to as an instance of the ANRORC mechanism : nucleophilic addition (A N ), ring opening and ring closing . Applications
Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called "mixed acid." The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (ΔH = −117 kJ/mol). [5] +