sign up I login
 advanced
refer a friend - earn nickels!!

Ask & Discuss Questions with Community & Experts

Moderation Team
Ask iit jee aieee pet cbse icse state board community Discussion Response Post to: hyperconjugation and resonance : clear solution !!!!
Forum Index -> Community shelf -> View Full Question like the article? email it to a friend.  
Author Message
coolriya (482)

Blazing goIITian

Olaaa!! Perrrfect answer. 88  [109 rates]

coolriya's Avatar

total posts: 468    
offline Offline
What is Hyperconjugation ?


Hyperconjugation is the stabilising interaction that results from the interaction of the electrons in a s-bond (usually C-H or C-C) with an adjacent empty (or partially filled) p-orbital or a p-orbital to give an extended molecular orbital that increases the stability of the system.
Based on the valence bond model of bonding, hyperconjugation can be described as "double bond - no bond resonance" but it is not what we would "normally" call resonance, though the similarity is shown below.
What is the key difference between hyperconjugation and resonance ?
"hyperconjugation involves a sigma orbital component, resonance is just pi orbitals " 
Hyperconjugation is a factor in explaining why increasing the number of alkyl substituents on a carbocation or radical centre leads to an increase in stability.
 
Let's consider how a methyl group is involved in hyperconjugation with a carbocation centre. 
interaction of a methyl group
First we need to draw it to show the C-H s-bonds.
Note that the empty p orbital associated with the positive charge at the carbocation centre is in the same plane (i.e. coplanar) with one of the C-H s-bonds  (shown in blue.)
look at the sigma bonds
This geometry means the electrons in the s-bond can be stabilised by an interaction with the empty p-orbital of the carbocation centre.
(this diagram shows the similarity with resonance and the structure on the right has the "double bond - no bond" character)
electrons in the sigma bond interact with the empty p orbital
The stabilisation arises because the orbital interaction leads to the electrons being in a lower energy orbital
 

orbital interaction diagram

 

Of course, the C-C s-bond is free to rotate, and as it does so, each of the C-H s-bonds in turn undergoes the stabilising interaction.
So the ethyl cation has 3 C-H s-bonds that can be involved in hyperconjugation.
The more hyperconjuagtion there is, the greater the stabilisation of the system.
So for example, the t-butyl cation has 9 C-H s-bonds that can be involved in hyperconjugation. Hence (CH3)3C+ is more stable than CH3CH2+
The effect is not limited to C-H s-bonds, appropriate C-C s-bonds can also be involved in hyperconjugation.


hope u would have got evrythin clear...........


Glitter Word Generator
 this article: 20 points  (with Olaaa!! Perrrfect answer.   in 4 votes )   [?]
 
You have to be logged on to rate
  
 

Top Offers for goIITians
Correspondence Courses
Brilliant Tutorials
Narayana Institute
Aakash Institute
Classroom/Crash Courses
Narayana - Kota , Delhi , Others
Brilliant Tutorials - Class , Crash
Aakash Institute - Medical , Engg
Online Test Series
Brilliant Tutorials
Narayana Institute
Aakash Institute
Mahesh Tutorials
AMITY      Sri Chaitanya