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Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C 6 H 5 Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. [6]
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:
In this way the two halogens add in an anti addition fashion, and when the alkene is part of a cycle the dibromide adopts the trans configuration. For maximum overlap of the C–Br σ* antibonding molecular orbital (the LUMO , shown to the right in red) and the nucleophile (X − ) lone pair (the HOMO , shown to the right below in green), X − ...
Other products such as CH 2 Cl 2 may also form. Chain termination Two free radicals (chlorine and chlorine, chlorine and methyl, or methyl and methyl) combine: Methane chlorination: termination The last possibility generates in an impurity in the final mixture (notably, an organic molecule with a longer carbon chain than the reactants).
Substituents add ortho to the amine in diethyl-(meta-trifluoromethyl)aniline and ortho to the fluoride in para-fluorobenzaldehyde; When multiple substituents are comparably activating, steric hindrance dominates regioselectivity. Substituents add ortho to the methyl group in para-(tert-butyl)toluene
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:
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C 7 H 5 ClO.It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring (C 6 H 6) with an acyl chloride (−C(=O)Cl) substituent.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C 6 H 5 CH 2 Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block .