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Electrophilic Addition

In electrophilic addition to carbon-carbon double bonds, a positive species approaches in the first step converting the pair of π-electrons into an s-pair. As in electrophilic substitution, the approaching species need not actually be a positive ion but may be the positive end of a dipole or induced dipole.

Bromohydrin formation is an example of electrophilic addition to an alkene initiated by attack of a proton and subsequent reaction with bromide ion. This reaction is stereospecific and is an example of anti-addition. Thus, reaction of a C=C bond in the intermediate (I) with HBr results in the stereospecific formation of the bromohydrin (II). This compound may subsequently be converted to the antimitotic drug Podofilox (III).

electrophilic addition formula

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