Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
The electrons of a double bond are more loosely held than those of the bond. As a result, the electrons which extend above and below the molecular plane of the
alkene, can act as a nucleophile in a manner similar to that of more typical Lewis bases.
2,3-dimethylbutene
The electrophilic addition reactions of alkenes can be both regioselective and stereospecific.
At low temperatures, and with a good nucleophile, an electrophilic addition product is formed.
Typically, the gaseous HX (HCl, HBr, or HI) is bubbled through the pure or dissolved alkene. The reaction can also be carried out in a solvent such as acetic acid.
If the carbon atoms participating in the double bond are not equally substituted, the proton from the hydrogen halide attaches itself to the less substituted carbon. The halogen, as a result attaches to the more substituted carbon. This result is known as Markovnikovs rule and is based on the stability of the carbocation formed by the addition of the proton.
HX adds to unsymmetric alkenes in a way that the initial protonation gives the more stable carbocation.
Product mixures will be formed from alkenes that are similarly substituted at both sp2 carbon atoms. If addition to an achiral alkene generates a chiral product, a racemic mixure will be obtained.
The reaction with bromine results in a color change from red to colorless, which is sometimes used as a test for unsaturation. Halogenations are best carried out at or below room temperature and in inert halogenated solvents (i.e. - halomethanes)
Only anti addition is observed. The product is racemic since the initial attack of bromine can occur with equal probability at either face of the cyclohexene.
The water molecule is added anti to the bromine atom and the other product is HBr.
Vicinal haloethers can be produced if an alcohol is used as the solvent, rather than water.
The alcohol obtained from oxymercuration-demercuration is the same as that obtained from Markovnikov hydration, however since no carbocation is involved in the reaction mechanism, rearrangements of the transition state do not occur.