Explanation
The rule states that, with the addition of a protic acid HX to an alkene, the acid hydrogen (H) becomes attached to the carbon with fewer alkyl substituents, and the halide (X) group becomes attached to the carbon with more alkyl substituents.
The same is true when an alkene reacts with water in an addition reaction to form alcohol. The hydroxyl group (OH) bonds to the carbon that has the greater number of carbon-carbon bonds, while the hydrogen bonds to the carbon on the other end of the double bond, that has more carbon-hydrogen bonds.
The chemical basis for Markovnikov's Rule is the formation of the most stable carbocation during the addition process. The addition of the hydrogen (in the form of a proton) to one carbon atom in the alkene creates a positive charge on the other carbon, forming a carbocation intermediate. The more substituted the carbocation (the more bonds it has to carbon or to electron-donating substituents) the more stable it is, due to induction and hyperconjugation. The major product of the addition reaction will be the one formed from the more stable intermediate. Therefore, the major product of the addition of HX (where X is some atom more electronegative than H) to an alkene has the hydrogen atom in the less substituted position and X in the more substituted position. However, the other less substituted, less stable carbocation will still be formed to some degree, and will proceed to form the minor product with the opposite attachment of X.
Read more about this topic: Markovnikov's Rule
Famous quotes containing the word explanation:
“To develop an empiricist account of science is to depict it as involving a search for truth only about the empirical world, about what is actual and observable.... It must involve throughout a resolute rejection of the demand for an explanation of the regularities in the observable course of nature, by means of truths concerning a reality beyond what is actual and observable, as a demand which plays no role in the scientific enterprise.”
—Bas Van Fraassen (b. 1941)
“Are cans constitutionally iffy? Whenever, that is, we say that we can do something, or could do something, or could have done something, is there an if in the offingsuppressed, it may be, but due nevertheless to appear when we set out our sentence in full or when we give an explanation of its meaning?”
—J.L. (John Langshaw)
“There is a great deal of unmapped country within us which would have to be taken into account in an explanation of our gusts and storms.”
—George Eliot [Mary Ann (or Marian)