Open main menu
Home
Random
Recent changes
Special pages
Community portal
Preferences
About Wikipedia
Disclaimers
Incubator escapee wiki
Search
User menu
Talk
Dark mode
Contributions
Create account
Log in
Editing
Markovnikov's rule
(section)
Warning:
You are not logged in. Your IP address will be publicly visible if you make any edits. If you
log in
or
create an account
, your edits will be attributed to your username, along with other benefits.
Anti-spam check. Do
not
fill this in!
==Explanation== The rule states that with the addition of a [[protic acid]] HX or other polar reagent to an asymmetric [[alkene]], the acid hydrogen (H) or electropositive part gets attached to the carbon with more hydrogen substituents, and the [[halide]] (X) group or electronegative part gets attached to the carbon with more alkyl substituents. This is in contrast to Markovnikov's original definition, in which the rule states that the X component is added to the carbon with the fewest hydrogen atoms while the hydrogen atom is added to the carbon with the greatest number of hydrogen atoms.<ref>{{cite book |title= Organic Chemistry |edition= 8th |first= John |last= McMurry |chapter= Section 7.8: Orientation of Electrophilic Reactions: Markovnikov's Rule |page= 240 |isbn= 9780840054548 }}</ref> [[File:Markovnikov vs anti-Markovnikov.svg|center|500px]] The same is true when an alkene reacts with water in an additional reaction to form an alcohol that involves carbocation formation. 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. Adding the hydrogen ion 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 stable it is, due to [[inductive effects|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. But the other less substituted, less stable carbocation will still be formed at some concentration and will proceed to be the minor product with the opposite, conjugate attachment of X.
Edit summary
(Briefly describe your changes)
By publishing changes, you agree to the
Terms of Use
, and you irrevocably agree to release your contribution under the
CC BY-SA 4.0 License
and the
GFDL
. You agree that a hyperlink or URL is sufficient attribution under the Creative Commons license.
Cancel
Editing help
(opens in new window)