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For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively. Likewise, whereas both benzene and naphthalene can be alkylated using Friedel–Crafts reaction conditions, naphthalene can also be easily alkylated by reaction with alkenes or alcohols , using ...
The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction:
The reaction proceeds through generation of an acylium center. The reaction is completed by deprotonation of the arenium ion by AlCl 4 −, regenerating the AlCl 3 catalyst. However, in contrast to the truly catalytic alkylation reaction, the formed ketone is a moderate Lewis base, which forms a complex with the strong Lewis acid aluminum ...
The sulfonation with fuming sulfuric acid gives benzenesulfonic acid. Aromatic halogenation with bromine, chlorine, or iodine gives the corresponding aryl halides. This reaction is typically catalyzed by the corresponding iron or aluminum trihalide. The Friedel–Crafts reaction can be performed either as an acylation or as an alkylation.
Chloroacetic acid was first prepared (in impure form) by the French chemist Félix LeBlanc (1813–1886) in 1843 by chlorinating acetic acid in the presence of sunlight, [3] and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing glacial acetic acid in the presence of chlorine and sunlight, [4] and then by the French chemist Charles Adolphe Wurtz by ...
Chloroacetic acid is mainly made by hydrolysing trichloroethylene in the presence of sulfuric acid: CCl 2 =CHCl + 2 H 2 O → CH 2 ClCOOH + 2 HCl; Dichloroacetic acid is manufactured in small quantities by reducing trichloroacetic acid. Trichloroacetic acid is made by directly reacting chlorine with acetic acid using a suitable catalyst.
The most commonly employed Sandmeyer reactions are the chlorination, bromination, cyanation, and hydroxylation reactions using CuCl, CuBr, CuCN, and Cu 2 O, respectively. More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction.
2-Chloronaphthalene is obtained directly by chlorination of naphthalene, with the formation of more highly substituted derivatives such as dichloro- and trichloronaphthalenes, in addition to the two monochlorinated isomeric compounds: 1-chloronaphthalene and 2-chloronaphthalene.