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Unlike the complex transformations of combustion, the halogenation of an alkane appears to be a simple substitution reaction in which a C-H bond is broken and a new C-X bond is formed. The chlorination of methane, shown below, provides a simple example of this reaction.
Halogenation of an alkane produces a hydrocarbon derivative in which one or more halogen atoms have been substituted for hydrogen atoms. Alkanes are notoriously unreactive compounds because they are non-polar and lack functional groups at which reactions can take place.
Reactivity Comparison of Halogenation; When alkanes react with halogen (Cl 2 or Br 2), with heat or light, hydrogen atom of the alkane is replaced by halogen atom and alkyl halide is produced as product. This can be generally shown as:
One of these reactions is halogenation, or the substitution of a single hydrogen on the alkane for a single halogen to form a haloalkane. This reaction is very important in organic chemistry because it opens a gateway to further chemical reactions.
9.2 Halogenation Reaction of Alkanes. When alkanes react with halogen (Cl 2 or Br 2), with heat or light, the hydrogen atom of the alkane is replaced by a halogen atom, and alkyl halide is produced as a product. This can be generally shown as:
In this tutorial, we are going to talk about the radical halogenation of alkanes. We’ll go over the intricacies of the mechanism, how to find the major products in this reaction, and discuss the most important points of each mechanistic step.
Predict the products of halogenation reaction of alkanes. Be able to draw the mechanism of radical halogenation of alkanes. Explain the thermodynamics of halogenation reactions.
In the halogenation of an alkane, the alkane is stated to undergo either chlorination, fluorination, iodination, or bromination, depending on the identity of the halogen reactant. Bromination and Chlorination are the alkane halogenation reactions that are used widely.
In this post we’re going to begin building our reaction map, starting with the simplest organic compounds of all: alkanes.*We’ve only learned one synthetically important class of alkane reaction: free-radical halogenation.
Halogenation At Tiffany’s. Thinking Through The Selectivity of Bromination vs Chlorination: An Intuitive Analogy. As we discussed in the last post on radicals, bromine radicals are considerably more selective than chlorine radicals in the halogenation of alkanes.