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Photon336

  • one year ago

@woodward @rushwr

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  1. Photon336
    • one year ago
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    |dw:1442549583564:dw|

  2. Photon336
    • one year ago
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    fun problem

  3. Photon336
    • one year ago
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    |dw:1442549747491:dw|

  4. Photon336
    • one year ago
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    I should have just drawn it originally in the ring form not the chair form. btw that bond should be facing downwards bad @ chair form

  5. Photon336
    • one year ago
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    |dw:1442549967650:dw| Never underestimate the power of this group, you can make a lot of compounds from it

  6. Photon336
    • one year ago
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    |dw:1442550160419:dw|

  7. Photon336
    • one year ago
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    |dw:1442550568373:dw|

  8. Photon336
    • one year ago
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    @Rushwr you're learning organic in HS? dammm!

  9. Photon336
    • one year ago
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    yep that R group just means the part of the molecule i'm too lazy to draw

  10. Photon336
    • one year ago
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    woodward you missed the show i'm going to post another

  11. Photon336
    • one year ago
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    @Woodward "what happens when an aldehyde and dilute acid are mixed?"

  12. Photon336
    • one year ago
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    I got this one wrong TO the above question A. Hydroxyl aldehyde B. Carboxylic acid by oxidation C. Ketone D. Carboxylic acid, tautomerization

  13. Photon336
    • one year ago
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    |dw:1442550880362:dw|

  14. Photon336
    • one year ago
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    I got this wrong

  15. anonymous
    • one year ago
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    This looks like an aldol condensation reaction eh?

  16. Photon336
    • one year ago
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    @Woodward you're correct it's aldol but I would like to go through it too

  17. Photon336
    • one year ago
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    Must be acid catalyzed aldol

  18. Photon336
    • one year ago
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    forgot how it goes though

  19. anonymous
    • one year ago
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    |dw:1442551139689:dw|

  20. Photon336
    • one year ago
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    |dw:1442551267078:dw|

  21. Photon336
    • one year ago
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    @Woodward omg that's beautiful

  22. anonymous
    • one year ago
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    I'll go ahead and finish the reaction since this isn't done yet, but I'm not sure if the steps I do are the actual mechanism give me a second since this alcohol will combine with an aldehyde in solution (ald-ol) afterall.

  23. Photon336
    • one year ago
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    |dw:1442551437303:dw|

  24. anonymous
    • one year ago
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    Yeah exactly this is what happens, then it dehydrates

  25. anonymous
    • one year ago
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    |dw:1442551591491:dw|

  26. anonymous
    • one year ago
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    So this is pretty common for doing an acid-catalyzed aldol condensation, it is unavoidable most of the time since you're in the conditions of heat with an acidic alpha hydrogen there, it will go through the standard acid-catalyzed dehydration to form a double bond! This is why we aren't getting an aldol as the final product @Rushwr but we would if we had done this with a base.

  27. Photon336
    • one year ago
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    |dw:1442551772220:dw|

  28. anonymous
    • one year ago
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    |dw:1442551901895:dw| |dw:1442551920421:dw| Also when I talk about "alpha hydrogen" I am specifically referring to relative to the carbonyl group, it's more acidic than normal. Think of this as like an allylic position, because that's essentially why the alpha hydrogen can be lost like this, it's more clear to see the resonance stabilization in a basic conditions,

  29. anonymous
    • one year ago
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    |dw:1442552085639:dw|

  30. Photon336
    • one year ago
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    |dw:1442551990377:dw| following though with this myself

  31. Photon336
    • one year ago
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    awesome job woodward

  32. anonymous
    • one year ago
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    Yeah this is a lot of fun, ask any more questions if something's unclear or if you want to try to test this further. Like for example, the acid-catalyzed aldol condensation can also tend to react twice, since it creates another aldehyde which is different from the reactant aldehydes. :O

  33. anonymous
    • one year ago
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    See if you can find a possible pathway to this for fun: |dw:1442552375934:dw|

  34. Photon336
    • one year ago
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    Yeah

  35. anonymous
    • one year ago
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    Sure let's do it :D

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