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nincompoop

  • one year ago

acidic @zale101

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  1. nincompoop
    • one year ago
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    |dw:1442462330999:dw|

  2. nincompoop
    • one year ago
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    which proton is more acidic

  3. Zale101
    • one year ago
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    A?

  4. nincompoop
    • one year ago
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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

  5. Zale101
    • one year ago
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    Can you show me how you change it to conjugate base like you said in the chat?@

  6. nincompoop
    • one year ago
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    |dw:1442462707722:dw|

  7. Zale101
    • one year ago
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    Then b would be less basic than a?

  8. nincompoop
    • one year ago
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    okay let us define acid

  9. Zale101
    • one year ago
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    well, an acid is electron loving (electronphiles) and donates protons.

  10. nincompoop
    • one year ago
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    proton donor, and correct that acid is an electrophilic then we can say that stronger acid generates weaker base weaker acid generates stronger base

  11. Zale101
    • one year ago
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    Yes, weaker acid makes the reaction favors the reactant or products on where the weaker acid is on

  12. nincompoop
    • one year ago
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    so which of the two has weaker conjugate base?

  13. Zale101
    • one year ago
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    You said b is more acidic, then it has the weaker base.

  14. nincompoop
    • one year ago
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    remember strong acid creates weak base

  15. Photon336
    • one year ago
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    Another useful mnemonic for comparing acidity: ARIO A = atom R = resonance I = induction O = orbital

  16. nincompoop
    • one year ago
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    the negative charge is more stable with the triple bond - sp hybridize carbon atom than the negative charge of sp3 hybridized nitrogen

  17. Zale101
    • one year ago
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    Nin, give me another problem.

  18. nincompoop
    • one year ago
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  19. Zale101
    • one year ago
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    is that from david klein's book?@

  20. nincompoop
    • one year ago
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    ye :)

  21. nincompoop
    • one year ago
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    I can upload from other books as well

  22. nincompoop
    • one year ago
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    do you want something more straight-forward?

  23. Zale101
    • one year ago
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    Sure.

  24. nincompoop
    • one year ago
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  25. nincompoop
    • one year ago
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    you can pick from 3.25, 3.26 that you think gives you a little problem

  26. Zale101
    • one year ago
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    in a, the red h, proton, is more acidic because it is capable of more resonance

  27. Zale101
    • one year ago
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    3.25 a

  28. Zale101
    • one year ago
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    3.25 b is proton red?

  29. nincompoop
    • one year ago
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    it has more resonance than the other?

  30. nincompoop
    • one year ago
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    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?

  31. Zale101
    • one year ago
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    The negative charge can create a lone pair on the oxygen, can go all over the other carbons

  32. nincompoop
    • one year ago
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    see you around

  33. Zale101
    • one year ago
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    See you.

  34. Zale101
    • one year ago
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    :)

  35. Zale101
    • one year ago
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    |dw:1442507895808:dw|

  36. Zale101
    • one year ago
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    |dw:1442507985952:dw|

  37. Zale101
    • one year ago
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    |dw:1442509064236:dw|

  38. Zale101
    • one year ago
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    |dw:1442509108193:dw|

  39. nincompoop
    • one year ago
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    I was in the lab all day what's up???

  40. nincompoop
    • one year ago
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    continue practicing and do not stop until you are 110% confident

  41. nincompoop
    • one year ago
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    @empty

  42. nincompoop
    • one year ago
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    |dw:1442545873587:dw|

  43. anonymous
    • one year ago
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    |dw:1442546460525:dw|

  44. anonymous
    • one year ago
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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.

  45. anonymous
    • one year ago
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    hence, stronger acids have greater Ka values and more negative pKa values.

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