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Bromotoluenes are aryl bromides based on toluene in which at least one aromatic hydrogen atom is replaced with a bromine atom. They have the general formula C 7 H 8– n Br n , where n = 1–5 is the number of bromine atoms.
For example, consider radical bromination of toluene: [5] bromination of toluene with hydrobromic acid and hydrogen peroxide in water. This reaction takes place on water instead of an organic solvent and the bromine is obtained from oxidation of hydrobromic acid with hydrogen peroxide. An incandescent light bulb suffices to radicalize.
Nitration of toluene gives mono-, di-, and trinitrotoluene, all of which are widely used. Dinitrotoluene is the precursor to toluene diisocyanate, a precursor to polyurethane foam. Trinitrotoluene (TNT) is an explosive. Complete hydrogenation of toluene gives methylcyclohexane. The reaction requires a high pressure of hydrogen and a catalyst.
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.
Reaction of toluene to produce benzene and xylene. Transalkylation, as used by the petrochemical industry, is often used to convert toluene into benzene and xylenes. This is achieved through a disproportionation reaction of toluene in which one toluene molecule transfers its methyl group to another one. The reaction is not selective, and the ...
Iodination and bromination can be effected by the addition of iodine and bromine to alkenes. The reaction, which conveniently proceeds with the discharge of the color of I 2 and Br 2, is the basis of the analytical method. The iodine number and bromine number are measures of the degree of unsaturation for fats and other organic compounds.
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:
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 ...