Markownikoff's Rule: Why Does it Happen?

  • Thread starter Thread starter Saoist
  • Start date Start date
AI Thread Summary
The discussion centers on understanding Markovnikov's rule, which explains the regioselectivity of electrophilic addition reactions, particularly in alkenes. Initially based on empirical observations, the rule predicts that when HX (like HCl) adds to an alkene, the hydrogen atom will bond to the carbon with more hydrogen substituents, while the halide will attach to the more substituted carbon. This preference is rationalized through the stability of carbocations formed during the reaction mechanism. A more substituted carbocation is more stable due to hyperconjugation and inductive effects, making it more favorable for nucleophiles to attack at that position. The example of 1-Methyl-2-butene illustrates this, where the addition of HCl results in the halide attaching to the more substituted carbon due to the partial positive charge created during the reaction.
Saoist
Messages
28
Reaction score
0
looked in books/googled for info about this...i know what it IS, but don't understand why it happens. anyone?
 
Chemistry news on Phys.org
Originally it was based on empirical evidence (it was just the product that you got from certain reactions) and was used as a predictive tool. It can be rationilized by thinking about the intermediates of a reaction mechanism. If a carbocation is formed then it will be more stable at the more substituted carbon and therefore a nucleophile would be more likely to attack at that position.
 
Well, I ain't sure of this but consider a 1-Methyl-2-butene. When HCl adds across the double bond, Cl radical will attract the electrons of the C=C towards itself creating a partial +ve charge on the C atoms. This partial positive charge is handled better by a 3rd degree C atom than the 2nd degree C atom. Thus the -ve part of the addendum will go the the C with more substituents, which is the Markonikov's rule.
 

Thread 'Solubility of MgSO47H2O in water'

It seems like a simple enough question: what is the solubility of epsom salt in water at 20°C? A graph or table showing how it varies with temperature would be a bonus. But upon searching the internet I have been unable to determine this with confidence. Wikipedia gives the value of 113g/100ml. But other sources disagree and I can't find a definitive source for the information. I even asked chatgpt but it couldn't be sure either. I thought, naively, that this would be easy to look up without...
View full post »

Thread 'Why does having 8 valence electrons make an element inert?'

I was introduced to the Octet Rule recently and make me wonder, why does 8 valence electrons or a full p orbital always make an element inert? What is so special with a full p orbital? Like take Calcium for an example, its outer orbital is filled but its only the s orbital thats filled so its still reactive not so much as the Alkaline metals but still pretty reactive. Can someone explain it to me? Thanks!!
View full post »

Similar threads

Please explain the reaction between Potassium carbonate and Magnesium
Replies
5
Views
2K
Could microfiber cloth be toxic?
Replies
13
Views
6K
What exactly happens during a phase change?
Replies
10
Views
2K
Rationale for 6n+2 rule for the number of pi bonds in a non-cyclic molecule
Replies
3
Views
1K
Why is Potassium Nitride (K3N) unstable?
Replies
3
Views
2K
Solubility of Sodium nitrate and nitrite
Replies
3
Views
2K
Why does having 8 valence electrons make an element inert?
Replies
8
Views
215
My 'why' questions -- Wanting to learn Chemistry to figure out my why questions
Replies
11
Views
3K
Does the Reaction of Cl2 and KH Produce KCl and HCl?
Replies
5
Views
2K
Calcium in Anhydrous Calcium Chloride
Replies
5
Views
2K

Hot Threads

Recent Insights

Back
Top