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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:
The most widely practised example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999. [2] (After dehydrogenation and polymerization, the commodity plastic polystyrene is produced.) In this process, acids are used as catalyst to generate the incipient carbocation. Many other electrophilic reactions ...
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:
Chlorine is slightly more selective, but still reacts with most metals and heavier nonmetals. Following the usual trend, bromine is less reactive and iodine least of all. Of the many reactions possible, illustrative is the formation of gold(III) chloride by the chlorination of gold.
A good example of a substitution reaction is halogenation. When chlorine gas (Cl 2) is irradiated, some of the molecules are split into two chlorine radicals (Cl•), whose free electrons are strongly nucleophilic. One of them breaks a C–H covalent bond in CH 4 and grabs the hydrogen atom to form the electrically neutral HCl.
Addition reactions are also encountered in polymerizations and called addition polymerization. General overview of addition reactions. Top to bottom: electrophilic addition to alkene, nucleophilic addition of nucleophile to carbonyl and free-radical addition of halide to alkene. Depending on the product structure, it could promptly react ...
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:
A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group. [1] The general chemical formula of the halogen addition reaction is: C=C + X 2 → X−C−C−X (X represents the halogens bromine or chlorine, and in this case, a solvent could be CH 2 ...