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  2. Free-radical halogenation - Wikipedia

    en.wikipedia.org/wiki/Free-radical_halogenation

    The relative rates at which different halogens react vary considerably: [citation needed] fluorine (108) > chlorine (1) > bromine (7 × 10 −11) > iodine (2 × 10 −22).. Radical fluorination with the pure element is difficult to control and highly exothermic; care must be taken to prevent an explosion or a runaway reaction.

  3. Halogen addition reaction - Wikipedia

    en.wikipedia.org/wiki/Halogen_addition_reaction

    As it attacks and forms a bond with one of the carbons, the bond between the first bromine atom and the other carbon atoms breaks, leaving each carbon atom with a halogen substituent. 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.

  4. Photochlorination - Wikipedia

    en.wikipedia.org/wiki/Photochlorination

    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 ...

  5. Electrophilic halogenation - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_halogenation

    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).

  6. Dehydrohalogenation - Wikipedia

    en.wikipedia.org/wiki/Dehydrohalogenation

    where B is a basic ligand such as a pyridine, X is a halogen (typically chlorine or bromine), M is a metal such as cobalt, copper, zinc, palladium or platinum, and L n are spectator ligands. References

  7. Toluene - Wikipedia

    en.wikipedia.org/wiki/Toluene

    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 ...

  8. Chlorotoluene - Wikipedia

    en.wikipedia.org/wiki/Chlorotoluene

    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.

  9. Benzyl chloride - Wikipedia

    en.wikipedia.org/wiki/Benzyl_chloride

    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]