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Reaction with Halogens

Alkenes react readily with halogens at room temperature and in the dark. The reaction of alkenes with bromine is used as a test for a C=C double bond. Alkenes will turn bromine water from orange to colourless. The mechanism of the reaction is electrophilic addition.When the non-polar bromine molecule approaches the alkene in a particular orientation, the repulsion of the bonding pair of electrons by the electron dense region of the C=C double bond causes heterolytic fission. The positive Br+ ion then forms a bond with the π electrons and a carbocation and negative bromide ion remains. The negative bromide ion forms a bond with the positive carbon ion forming a dibromoalkane.Alkenes react with chlorine and iodine in a similar way.

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Specification: OCR Chemistry A (H432), A-level, 4.1.3 Alkenes. Topic: Alkenes.

Key terms in this lesson

heterolytic fission
The breaking of a covalent bond in which both electrons of the bonded pair go to the same atom, forming a positive and a negative ion.
carbocation
A positively charged carbon-containing ion, formed when a carbon atom has only three bonds and a positive charge.

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