Comparing Basicity and Nucleophilicity in Organic Reactions

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In summary, the product of an organic compound is determined by the catalyst, reagent, and the conditions of the reaction.
  • #1
phymatter
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I have read that basicity is compared by equlibrium and nucleophilicity by kinetics , then how do we compare basicity with nucleophilicity ??
That is if there is a negatively charged molecule and H+ and a carbocation , how do we come to know which will be attacked by the negatively charged molecule ?
 
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  • #2
You should realize that nucleophilicity does not require a negatively charged molecule. Neither does a base. If we were to have a base and a nucleophile present with a carbocation and a proton, the base would most likely react with the proton most rapidly. Nothing imposes any restriction on the approach of the proton to the base since the bare proton's reactive face is 'omnidirectional'. The reactive side of the base is likely localized to a particular location on one side or the other of that molecule, so the approach of the proton to the base must occur from one side of the base only. A nucleophile (it can be negatively charged) has the same requirement as a base but since no information is given (in your question) as to it's shape or charge distribution, nothing can be said about its rate of reaction.

In the example of the carbocation and nucleophile (even negatively charged ones), both faces of the reactants must line up and approach each other in a particular fashion and with a particular energy. This imposes somewhat of a limitation on the degrees of freedom allowed for the reaction to proceed to completion resulting in a slower reaction rate.

The upshot is that protonation is much faster than either SN1 or SN2 type reactions.
 
  • #3
what is the criteria that weather a given reaction is sn1 or sn2?
 
  • #4
how can we determine the product of an organic compound according to the catalyst,reagent...that are given in the reaction process?
 
  • #5
phymatter said:
I have read that basicity is compared by equlibrium and nucleophilicity by kinetics , then how do we compare basicity with nucleophilicity ??
That is if there is a negatively charged molecule and H+ and a carbocation , how do we come to know which will be attacked by the negatively charged molecule ?

One thing to think about is that equilibrium is the point where the forward reaction rate is equal to the reverse reaction rate. With equilibrium you are concerned about the energy difference between reactants and products, but in a kinetics problem you're more concerned with the energy difference between the reactants and the activated state.
 
  • #6
One thing to think about is that equilibrium is the point where the forward reaction rate is equal to the reverse reaction rate. With equilibrium you are concerned about the energy difference between reactants and products, but in a kinetics problem you're more concerned with the energy difference between the reactants and the activated state.

Yes ! that is exactly what my question is !
 
  • #7
kzeybelay1 said:
how can we determine the product of an organic compound according to the catalyst,reagent...that are given in the reaction process?
how can we determine the product of an organic compound according to the catalyst,reagent...that are given in the reaction process?
 
  • #8
kzeybelay1 said:
how can we determine the product of an organic compound according to the catalyst,reagent...that are given in the reaction process?

Hi,

This is what my question is all about and i really wnt to know this as, somewhere I am getting confused in this question and I will clear it out while let just want to know about this.


Thanks!
 

Related to Comparing Basicity and Nucleophilicity in Organic Reactions

1. What is the difference between nucleophilicity and basicity?

Nucleophilicity refers to the ability of a chemical species to donate a pair of electrons to form a new chemical bond. Basicity, on the other hand, refers to the ability of a species to accept a proton. While both concepts involve the donation or acceptance of electrons, the key difference is that nucleophilicity involves the formation of a new bond, while basicity involves the formation of a new acid-base pair.

2. How are nucleophilicity and basicity related?

Nucleophilicity and basicity are related in that both concepts involve the donation or acceptance of electrons. However, the factors that affect nucleophilicity and basicity may differ. For example, a highly polarizable species may be a strong nucleophile but a weak base, while a highly electronegative species may be a weak nucleophile but a strong base.

3. What factors affect nucleophilicity?

The factors that affect nucleophilicity include the charge and size of the nucleophile, as well as the solvent and the presence of other functional groups in the molecule. In general, larger and more negatively charged species tend to be stronger nucleophiles.

4. How does basicity affect a molecule's reactivity?

Basicity can greatly affect a molecule's reactivity. A high basicity can make a molecule more reactive towards acids, while a low basicity can make a molecule less reactive. Basicity can also affect the stability of a molecule, as highly basic molecules tend to be less stable and more reactive.

5. What is the relationship between nucleophilicity and leaving group ability?

The ability of a molecule to act as a nucleophile is inversely related to its ability to function as a leaving group. This means that a strong nucleophile is usually a poor leaving group, and vice versa. This is due to the different electronic requirements for these two roles in a reaction - a strong nucleophile needs a high electron density to donate, while a good leaving group needs a low electron density to accept.

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