How do I rank these leaving groups?

In summary, the conversation involved ranking the leaving group abilities of H2O, NH2, OH, I, and NH3 in order of increasing ability. The group discussed the concept of leaving groups and how they leave with a charge, as opposed to a free electron as in bond dissociation. They also referenced a pka values table and determined that the correct order is B<C<E<A<D, with the halogen (except F) being the best leaving group due to its stability. They also discussed developing an intuition for understanding why halogens are better leaving groups.
  • #1
Delta what
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1. The problem statement, all variables and given/known.
Rank the following leaving group in order of increasing ability to leave?
A) H2O B) NH2 C) OH D) I E) NH3

Homework Equations


Also not entirely sure the order of H2O and NH3. What should I be looking for to answer this portion of the question?
Also my study group believes the better leaving group is a halogen. Is that correct?

3. The Attempt at a Solution
I think the answer is
B<C<D<A<E
My study group thinks it may be B<C<A<E<D
 
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  • #3
fresh_42 said:
I'm not good in chemistry and don't know what "leaving" here means. Is it this:
https://en.wikipedia.org/wiki/Bond-dissociation_energy?

No it is not. What you had linked to is in regards to the bond dissociation of a molecule when creating, what I believe to be, a free radical. Or when the two substances dissociated from each other leave with an unpaired electron. A leaving group in my question deals with one that leaves with a charge or in the case with H2O and NH3, had a charge when attached but when it leaves the two groups have a zero charge.
Here is a wiki article fresh_42 on the leaving group.
https://en.wikipedia.org/wiki/Leaving_group
 
  • #4
I believe that the most effective leaving group is going to be the weakest base. So in this case the best way to figure it out would be to look at a table of pka values and rank them in order of which pka values are the lowest.
 
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  • #5
leaving-groups-copy.jpg
 
  • #6
I got that image from http://www.masterorganicchemistry.com/2011/04/12/what-makes-a-good-leaving-group/
So from that graph and using the pka values the order should be b<c<e<a<d.
It is very odd to me that a charged halogen is a better leaving group than a zero charged NH3 or H2O. My reasoning for why I think this is odd is because I tend to think the stability or ΔG is greater (G is lower in number) in the H2O and NH3 and the ΔG for the I- is to a lesser extent (or higher number in free energy). Due to the lower energy of the H2O and NH3 they would be a better leaving group. I know that I am wrong in this thinking but I am I totally off base here? Maybe I have the ΔG values incorrect and the halogen is more stable? Other than the pka values what would be a good way to develop my intuition as to why these halogens (except F) are better at leaving? Thanks!
 
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Related to How do I rank these leaving groups?

1. How do I determine the leaving group ability of a compound?

The leaving group ability of a compound is determined by its stability after leaving the molecule. Generally, the weaker the bond between the leaving group and the rest of the molecule, the better the leaving group ability. Other factors that can affect leaving group ability include electronegativity, size, and solvation effects.

2. What is the order of leaving group ability for common functional groups?

The general order of leaving group ability for common functional groups is: iodide > bromide > chloride > fluoride > hydroxide > water > alkoxide > amine. However, this order can be affected by the specific molecule and reaction conditions.

3. How does the solvent affect leaving group ability?

The solvent can affect leaving group ability by stabilizing the transition state during the reaction. For example, polar solvents can stabilize ionic intermediates, making the leaving group more likely to dissociate. Nonpolar solvents, on the other hand, can hinder leaving group ability by not stabilizing the transition state.

4. How does the structure of the molecule affect leaving group ability?

The structure of the molecule can affect leaving group ability in various ways. For instance, the electron-withdrawing or electron-donating groups attached to the leaving group can affect its stability. Additionally, steric hindrance can also play a role in the ability of a leaving group to dissociate from the molecule.

5. Can leaving group ability be predicted?

While there are general trends in leaving group ability, it is difficult to predict with certainty. The specific reaction conditions and other factors such as solvent and steric hindrance can greatly influence the leaving group ability of a compound. It is best to experimentally determine the leaving group ability of a specific compound in the desired reaction.

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