How do I rank these leaving groups?

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The discussion centers on ranking leaving groups based on their ability to depart during a chemical reaction. Participants suggest that the order of leaving groups should be determined by their basicity, with weaker bases making better leaving groups. The proposed rankings vary, with some suggesting B<C<D<A<E and others B<C<A<E<D. A key point made is that halogens, despite being charged, are often better leaving groups than neutral molecules like H2O and NH3 due to their stability and lower pKa values. The conversation emphasizes the importance of understanding pKa values and the nature of leaving groups to develop a deeper intuition in organic chemistry.
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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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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
 
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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leaving-groups-copy.jpg
 
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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