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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 overall reaction mechanism, denoted by the Hughes–Ingold mechanistic symbol S E Ar, [3] begins with the aromatic ring attacking the electrophile E + (2a). This step leads to the formation of a positively charged and delocalized cyclohexadienyl cation, also known as an arenium ion, Wheland intermediate, or arene σ-complex (2b).
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
Ethylbenzene is an organic compound with the formula C 6 H 5 CH 2 CH 3.It is a highly flammable, colorless liquid with an odor similar to that of gasoline.This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material.
Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C 6 H 5 Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.
Industrially, it is mainly produced by the reaction of hydrogen gas with bromine gas at 200–400 °C with a platinum catalyst. However, reduction of bromine with red phosphorus is a more practical way to produce hydrogen bromide in the laboratory: [2] 2 P + 6 H 2 O + 3 Br 2 → 6 HBr + 2 H 3 PO 3 H 3 PO 3 + H 2 O + Br 2 → 2 HBr + H 3 PO 4
High bromine concentrations: r(a/s) = k 2a /k 2s (1 + k 4a /k 3a [Br 2]) where r(a/s) is the ratio of addition to substitution, and the k values correspond to constants describing the specific reaction steps pictured above under Competing Pathways.
A bromophenol is an organic compound consisting of hydroxyl groups and bromine atoms bonded to a benzene ring. They may be viewed as hydroxyl derivatives of bromobenzene, or as brominated derivatives of phenol. There are five basic types of bromophenols (mono- to pentabromophenol) and 19 different bromophenols in total when positional isomerism ...