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  2. Free-radical halogenation - Wikipedia

    en.wikipedia.org/wiki/Free-radical_halogenation

    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.

  3. Bromotoluene - Wikipedia

    en.wikipedia.org/wiki/Bromotoluene

    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.

  4. Electrophilic aromatic substitution - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_aromatic...

    Although discussions of directing groups usually focus on electronic effects (e.g. EWG vs EDGs), steric effect can prove influential. Thus, nitration of toluene gives approximately 2:1 ortho vs para-nitrotoluene. In the case of tert-butylbenzene, however, the selectivity is reversed:73% of the product is 4-nitro-tert-butybenzene]]. [4]

  5. Electrophilic halogenation - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_halogenation

    Halogenation of phenols is faster in polar solvents in a basic environment due to the dissociation of phenol, with phenoxide ions being more susceptible to electrophilic attack as they are more electron-rich. Chlorination of toluene with chlorine without catalyst requires a polar solvent as well such as acetic acid.

  6. Halogenation - Wikipedia

    en.wikipedia.org/wiki/Halogenation

    Halogenation of saturated hydrocarbons is a substitution reaction. The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions.

  7. 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 ...

  8. Benzyl bromide - Wikipedia

    en.wikipedia.org/wiki/Benzyl_bromide

    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]

  9. Aryl halide - Wikipedia

    en.wikipedia.org/wiki/Aryl_halide

    For example, phenols and anilines react quickly with chlorine and bromine water to give multihalogenated products. Many detailed laboratory procedures are available. [ 5 ] For alkylbenzene derivatives, e.g. toluene , the alkyl positions tend to be halogenated by free radical conditions, whereas ring halogenation is favored in the presence of ...