Electrophilic addition reactions
are transformations in which reagents are added to compounds containing
multiple (double or triple) bonds. The mechanism goes via
carbocation intermediates, the formation of which is dictated again by
relative stability (compare with the SN1 reaction). The carbocations
formed in this type of reaction are trapped by nucleophiles, exactly as
in the SN1 reaction, with resultant formation of the addition product(s).
The following series of graphics may help you visualize the events occurring
during this reaction.
Unsaturated substrate (alkene or alkyne)
and electrophilic species (e.g. H+) come into close proximity.
Pi electrons from substrate are donated
towards the electrophile, bond formed between one of the carbon atoms in
the double bond and the electrophile.
Donation of electrons to electrophile
results in carbocation formation. Same stability rules apply as elsewhere
(3o>2o>1o).
Nucleophilic species approaches and donates
electron pair towards cation resulting in C-Nu bond formation.
Overall, the reaction results in addition
of an electrophile and nucleophile to the multiple bond.
The following animation puts these events is sequence:
When unsymmetrical substrates are employed, Markovnikoff addition occurs. Essentially, the major product of addition will be the one that results from the most stable cation intermediate. The following is an example:
Peter Norris, Ph.D. 1998