How do I rank these leaving groups?

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Discussion Overview

The discussion revolves around ranking various leaving groups in terms of their ability to leave during a chemical reaction. Participants explore concepts related to chemistry, particularly focusing on the properties that make a leaving group effective, such as basicity and pKa values.

Discussion Character

  • Homework-related
  • Debate/contested
  • Technical explanation

Main Points Raised

  • One participant proposes a ranking of leaving groups as B
  • Some participants discuss the relationship between leaving group ability and basicity, suggesting that weaker bases make better leaving groups.
  • There is a mention of using pKa values to determine the effectiveness of leaving groups, with one participant referencing a table of pKa values.
  • One participant expresses confusion about the ranking of H2O and NH3, questioning their relative stability and leaving group ability.
  • Another participant challenges the idea that a charged halogen is a better leaving group than neutral molecules like NH3 or H2O, indicating a need for further intuition on this topic.
  • Links to external resources are provided for clarification on the concept of leaving groups and bond dissociation energy.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the ranking of the leaving groups, and there are multiple competing views regarding the factors that influence leaving group ability.

Contextual Notes

Some participants express uncertainty about the definitions and concepts involved, particularly regarding the nature of leaving groups and their relationship to bond dissociation energy and stability.

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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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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