Halogen addition reaction
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A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon-carbon double bond of an alkene functional group.
Here is the general chemical formula of the halogen addition reaction:
- C=C + X2 → X-C-C-X
(X represents the halogens bromine or chlorine, and in this case, a solvent could be CH2Cl2 or CCl4). The product is a vicinal dihalide.
This type of reaction is a halogenation and an electrophilic addition. The reaction mechanism for an alkene bromination can be described as follows (scheme 1). In the first step of the reaction, a bromine molecule approaches the electron-rich alkene carbon-carbon double bond. The bromine atom closer to the bond takes on a partial positive charge as its electrons are repelled by the electrons of the double bond.
The atom is electrophilic at this time and attacks the negatively charged, high energy pi bond portion of the alkene's carbon-carbon double bond. It forms for an instant a single sigma bond to both of the carbon atoms involved. The bonding of Bromine is special in this intermediate, due to its relatively large size compared to carbon, the bromide ion is capable to latching onto both carbons which once formed the π-bond, making a three-membered ring. acquiring a positive charge, which it shares slightly with the two carbon atoms. At this moment the halogen ion is called a "bromonium ion" or "chloronium ion", respectively.
When the first bromine atom attacks the carbon-carbon pi-bond, it leaves behind one of its electrons with the other bromine that it was bonded to in Br2. That other atom is now a negative bromide anion and is attracted to the slight positive charge on the Carbon atoms. It is blocked from nucleophilic attack on one side of the carbon chain by the first bromine atom and can only attack on the other side. 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.
The two halogens always add in a anti addition fashion, adopting the trans configuration.
[edit] See also
- Example of bromination in the Auwers synthesis
