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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:
Addition of Cl 2 destroys the aromaticity of the benzene ring, and the addition of two more Cl 2 molecules is rapid compared to the first. Hence, only thrice-dichlorinated product can be isolated from this reaction. Radical addition: C 6 H 6 + 3Cl 2 → C 6 H 6 Cl 6. Hexachlorocyclohexane isomers with more than one chlorine atom per carbon are:
Photochlorination is a chlorination reaction that is initiated by light. Usually a C-H bond is converted to a C-Cl bond. Photochlorination is carried out on an industrial scale. The process is exothermic and proceeds as a chain reaction initiated by the homolytic cleavage of molecular chlorine into chlorine radicals by ultraviolet radiation ...
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. Aromatic halogenation with bromine, chlorine, or iodine gives the corresponding aryl halides. This reaction is typically catalyzed by the corresponding iron or aluminum trihalide.
Mechanism of Blanc chloromethylation. Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 +) or chlorocarbenium cation (ClCH 2 +), which may be formed in the presence of zinc chloride. [4]
However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. [2] The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly ...
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:
Nucleophilic substitutions can proceed by two different mechanisms, unimolecular nucleophilic substitution (S N 1) and bimolecular nucleophilic substitution (S N 2). The two reactions are named according tho their rate law, with S N 1 having a first-order rate law, and S N 2 having a second-order. [2] S N 1 reaction mechanism occurring through ...