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