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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.
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: [3] C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl. In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. [4]
Reaction scheme of the photobromination of the methyl group of toluene. Photobromination with elemental bromine proceeds analogous to photochlorination also via a radical mechanism. In the presence of oxygen, the hydrogen bromide formed is partly oxidised back to bromine, resulting in an increased yield. Because of the easier dosage of the ...
These compounds are diazotized followed by treatment with cuprous chloride. [1] Industrially, the diazonium method is reserved for 3-chlorotoluene. The industrial route to 2- and 4-chlorotoluene entails direct reaction of toluene with chlorine. The more valuable 4-chlorotoluene is separated from 2-chlorotoluene by distillation.
Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction: The mechanism for bromination of benzene. The mechanism for iodination is slightly different: iodine (I 2) is treated with an oxidizing agent such as nitric acid to obtain the electrophilic iodine ("I +", probably IONO 2).
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.
Toluene is also found in cigarette smoke and car exhaust. If not in contact with air, toluene can remain unchanged in soil or water for a long time. [39] Toluene is a common solvent, e.g. for paints, paint thinners, silicone sealants, [40] many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and ...
Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. [6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. [3]