Photon336
  • Photon336
@woodward @rushwr
Chemistry
  • Stacey Warren - Expert brainly.com
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SOLVED
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katieb
  • katieb
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Photon336
  • Photon336
|dw:1442549583564:dw|
Photon336
  • Photon336
fun problem
Photon336
  • Photon336
|dw:1442549747491:dw|

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Photon336
  • Photon336
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
Photon336
  • Photon336
|dw:1442549967650:dw| Never underestimate the power of this group, you can make a lot of compounds from it
Photon336
  • Photon336
|dw:1442550160419:dw|
Photon336
  • Photon336
|dw:1442550568373:dw|
Photon336
  • Photon336
@Rushwr you're learning organic in HS? dammm!
Photon336
  • Photon336
yep that R group just means the part of the molecule i'm too lazy to draw
Photon336
  • Photon336
woodward you missed the show i'm going to post another
Photon336
  • Photon336
@Woodward "what happens when an aldehyde and dilute acid are mixed?"
Photon336
  • Photon336
I got this one wrong TO the above question A. Hydroxyl aldehyde B. Carboxylic acid by oxidation C. Ketone D. Carboxylic acid, tautomerization
Photon336
  • Photon336
|dw:1442550880362:dw|
Photon336
  • Photon336
I got this wrong
anonymous
  • anonymous
This looks like an aldol condensation reaction eh?
Photon336
  • Photon336
@Woodward you're correct it's aldol but I would like to go through it too
Photon336
  • Photon336
Must be acid catalyzed aldol
Photon336
  • Photon336
forgot how it goes though
anonymous
  • anonymous
|dw:1442551139689:dw|
Photon336
  • Photon336
|dw:1442551267078:dw|
Photon336
  • Photon336
@Woodward omg that's beautiful
anonymous
  • anonymous
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.
Photon336
  • Photon336
|dw:1442551437303:dw|
anonymous
  • anonymous
Yeah exactly this is what happens, then it dehydrates
anonymous
  • anonymous
|dw:1442551591491:dw|
anonymous
  • anonymous
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.
Photon336
  • Photon336
|dw:1442551772220:dw|
anonymous
  • anonymous
|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,
anonymous
  • anonymous
|dw:1442552085639:dw|
Photon336
  • Photon336
|dw:1442551990377:dw| following though with this myself
Photon336
  • Photon336
awesome job woodward
anonymous
  • anonymous
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
anonymous
  • anonymous
See if you can find a possible pathway to this for fun: |dw:1442552375934:dw|
Photon336
  • Photon336
Yeah
anonymous
  • anonymous
Sure let's do it :D

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