Conjugate of oxoacid

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RachaelKoh3A
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Joined: Fri Sep 28, 2018 12:25 am

Conjugate of oxoacid

Postby RachaelKoh3A » Mon Dec 03, 2018 1:57 pm

In the stabilization of oxoacid conjugates (like CCl3COO- or CBr3COO-) in which there are electron withdrawing atoms such as halogens, does it matter if the halogen is less electronegative than the oxygen atom?

Chem_Mod
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Re: Conjugate of oxoacid

Postby Chem_Mod » Mon Dec 03, 2018 3:08 pm

More electronegative atoms withdraw electrons more.

Andrewwiner4D
Posts: 32
Joined: Fri Sep 28, 2018 12:28 am

Re: Conjugate of oxoacid

Postby Andrewwiner4D » Mon Dec 03, 2018 4:28 pm

I know these are not the same acids but this is a good explanation Lavelle gave in 2014:
HOCl vs HOI --> To analyze the acidity of this pair you [censored] the polarizing power of the conjugate base (eg. -OCl and -OI). The more electronegative species (-OCl) will polarize ( pull charge towards it) the O-H bond. This withdraw away from the O-H bond weakens the bond (less electron density in the bond) and makes it easier to break. The O-H bond must be broken to form an acid hence it is stronger.

I talked about the halogen acids in discussion. As you go down the halogen column the elements get larger. Hence comparing the conjugate bases Cl- vs I- we see that I- is more stable because it is larger, which leads to I- being able to delocalize the negative charge over more volume leading to a lower energy state.


Let me know if this helped

RachaelKoh3A
Posts: 33
Joined: Fri Sep 28, 2018 12:25 am

Re: Conjugate of oxoacid

Postby RachaelKoh3A » Tue Dec 04, 2018 11:01 am

Yes, thank you!


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