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Topic: Scared...disconnection of an Aldol  (Read 4124 times)

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Offline a confused chiral girl

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Scared...disconnection of an Aldol
« on: December 03, 2006, 09:21:04 PM »
Hello,

I have spent over half an hour trying to take this apart. I tried to follow examples that I found on the site and also in my textbook. the first photo is the Aldol that I need to draw structures for the carbonyl electrophile and enolate nucleophile for. ...the second photo is what is what I did, which is wrong. I know this is self-condensation of an aldehyde, but I can't draw them. Please help me. Thank you!

Offline Yggdrasil

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Re: Scared...disconnection of an Aldol
« Reply #1 on: December 03, 2006, 10:30:05 PM »
Something which helps me with aldol reactions is to count the number of carbons in your product.  This should be equal to the combined number of carbons in your two reactants.  If you do this with your proposed answer, you will see why it is wrong and it will suggest a way to fix your reaction.

Offline a confused chiral girl

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Re: Scared...disconnection of an Aldol
« Reply #2 on: December 03, 2006, 10:54:59 PM »
yes, my textbook says to count the Carbons as well. that was what I did, and I just tried to draw it like this, but it does not look right to have electrons on the Carbon at the end. Is this what you mean? Please help me.

Offline Yggdrasil

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Re: Scared...disconnection of an Aldol
« Reply #3 on: December 03, 2006, 11:25:30 PM »
That is the correct answer.  Having the negative charge on the end is not a bad thing, especially because the negative charge is delocalized through resonance:

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