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Bromination of Methane

[ "article:topic", "authorname:clarkj", "showtoc:no" ]
  • Page ID
    3759
  • A Free Radical Substitution Reaction

    This page gives you the facts and a simple, uncluttered mechanism for the free radical substitution reaction between methane and bromine. This reaction between methane and bromine happens in the presence of ultraviolet light - typically sunlight. This is a good example of a photochemical reaction - a reaction brought about by light.

    \[CH_4 + Br_2 \rightarrow CH_3Br + HBr\]

    The organic product is bromomethane. One of the hydrogen atoms in the methane has been replaced by a bromine atom, so this is a substitution reaction. However, the reaction doesn't stop there, and all the hydrogens in the methane can in turn be replaced by bromine atoms.

    The mechanism

    The mechanism involves a chain reaction. During a chain reaction, for every reactive species you start off with, a new one is generated at the end - and this keeps the process going.The over-all process is known as free radical substitution, or as a free radical chain reaction.

    • Chain initiation: The chain is initiated (started) by UV light breaking a bromine molecule into free radicals.

    Br22Br

    • Chain propagation reactions: These are the reactions which keep the chain going.

    CH4  +  BrCH3  +  HBr

    CH3  +  Br2CH3Br  +  Br

    • Chain termination reactions: These are reactions which remove free radicals from the system without replacing them by new ones.

    2BrBr2

    CH3  +  BrCH3Br

    CH3  +  CH3CH3CH3

    Contributors

    Jim Clark (Chemguide.co.uk)