nincompoop
  • nincompoop
acidic @zale101
Organic
  • Stacey Warren - Expert brainly.com
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SOLVED
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katieb
  • katieb
I got my questions answered at brainly.com in under 10 minutes. Go to brainly.com now for free help!
nincompoop
  • nincompoop
|dw:1442462330999:dw|
nincompoop
  • nincompoop
which proton is more acidic
Zale101
  • Zale101
A?

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More answers

nincompoop
  • nincompoop
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
Zale101
  • Zale101
Can you show me how you change it to conjugate base like you said in the chat?@
nincompoop
  • nincompoop
|dw:1442462707722:dw|
Zale101
  • Zale101
Then b would be less basic than a?
nincompoop
  • nincompoop
okay let us define acid
Zale101
  • Zale101
well, an acid is electron loving (electronphiles) and donates protons.
nincompoop
  • nincompoop
proton donor, and correct that acid is an electrophilic then we can say that stronger acid generates weaker base weaker acid generates stronger base
Zale101
  • Zale101
Yes, weaker acid makes the reaction favors the reactant or products on where the weaker acid is on
nincompoop
  • nincompoop
so which of the two has weaker conjugate base?
Zale101
  • Zale101
You said b is more acidic, then it has the weaker base.
nincompoop
  • nincompoop
remember strong acid creates weak base
Photon336
  • Photon336
Another useful mnemonic for comparing acidity: ARIO A = atom R = resonance I = induction O = orbital
nincompoop
  • nincompoop
the negative charge is more stable with the triple bond - sp hybridize carbon atom than the negative charge of sp3 hybridized nitrogen
Zale101
  • Zale101
Nin, give me another problem.
nincompoop
  • nincompoop
Zale101
  • Zale101
is that from david klein's book?@
nincompoop
  • nincompoop
ye :)
nincompoop
  • nincompoop
I can upload from other books as well
nincompoop
  • nincompoop
do you want something more straight-forward?
Zale101
  • Zale101
Sure.
nincompoop
  • nincompoop
nincompoop
  • nincompoop
you can pick from 3.25, 3.26 that you think gives you a little problem
Zale101
  • Zale101
in a, the red h, proton, is more acidic because it is capable of more resonance
Zale101
  • Zale101
3.25 a
Zale101
  • Zale101
3.25 b is proton red?
nincompoop
  • nincompoop
it has more resonance than the other?
nincompoop
  • nincompoop
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?
Zale101
  • Zale101
The negative charge can create a lone pair on the oxygen, can go all over the other carbons
nincompoop
  • nincompoop
see you around
Zale101
  • Zale101
See you.
Zale101
  • Zale101
:)
Zale101
  • Zale101
|dw:1442507895808:dw|
Zale101
  • Zale101
|dw:1442507985952:dw|
Zale101
  • Zale101
|dw:1442509064236:dw|
Zale101
  • Zale101
|dw:1442509108193:dw|
nincompoop
  • nincompoop
I was in the lab all day what's up???
nincompoop
  • nincompoop
continue practicing and do not stop until you are 110% confident
nincompoop
  • nincompoop
@empty
nincompoop
  • nincompoop
|dw:1442545873587:dw|
anonymous
  • anonymous
|dw:1442546460525:dw|
anonymous
  • anonymous
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.
anonymous
  • anonymous
hence, stronger acids have greater Ka values and more negative pKa values.

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