acidic @zale101

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which proton is more acidic
A?

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you would think because of the Nitrogen right? but if you look at which is more stable after deprotonation (conjugate) , you will actually realize that B is more stable, there more B is more acidic
Can you show me how you change it to conjugate base like you said in the chat?@
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Then b would be less basic than a?
okay let us define acid
well, an acid is electron loving (electronphiles) and donates protons.
proton donor, and correct that acid is an electrophilic then we can say that stronger acid generates weaker base weaker acid generates stronger base
Yes, weaker acid makes the reaction favors the reactant or products on where the weaker acid is on
so which of the two has weaker conjugate base?
You said b is more acidic, then it has the weaker base.
remember strong acid creates weak base
Another useful mnemonic for comparing acidity: ARIO A = atom R = resonance I = induction O = orbital
the negative charge is more stable with the triple bond - sp hybridize carbon atom than the negative charge of sp3 hybridized nitrogen
Nin, give me another problem.
is that from david klein's book?@
ye :)
I can upload from other books as well
do you want something more straight-forward?
Sure.
you can pick from 3.25, 3.26 that you think gives you a little problem
in a, the red h, proton, is more acidic because it is capable of more resonance
3.25 a
3.25 b is proton red?
it has more resonance than the other?
delocalization of negative charge means more stable, therefore weaker base, therefore stronger acid .... so you now realize why my first question requires you to draw conjugate bases and see which is more stable?
The negative charge can create a lone pair on the oxygen, can go all over the other carbons
see you around
See you.
:)
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I was in the lab all day what's up???
continue practicing and do not stop until you are 110% confident
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In reference to your first structure, pKa of an amine group (nonprotonated) is about 40, pKa of alkyne is roughly 25. and as you should know by now, pKa is a measure of the conjugate base stability.
hence, stronger acids have greater Ka values and more negative pKa values.

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