Sciencemadness Discussion Board

formyl/acyl anion

lybra0076 - 29-9-2010 at 08:18

I understand the concept of creating a formyl/acyl anion to allow a reaction, but I don't really know what to bind to the compound to make it an anion.

madscientist - 29-9-2010 at 08:33

Not sure what you're trying to say. Could you rephrase that? What do you mean by "allow a reaction" and what compound are you referring to?

lybra0076 - 29-9-2010 at 08:38

sorry, ok, I'm referring to umpolungs, a compound that is created to force the carbon that is bonded to, say an oxygen, to have somewhat of a negative charge versus its normal positive charge (because of its bond with oxygen). I'm not sure if I made that any clearer...

lybra0076 - 29-9-2010 at 08:42

I have searched through my notes and online, and so far, I see that it needs to be bonded with....well, everything has the capital letter E. I'm not sure if that refers to E class functional groups or what...and in fact, if it does refer to those functional groups, why it does that because they normally cause electrophilic nature on the carbon. So, that just seems crazy.... =P

ScienceSquirrel - 29-9-2010 at 09:24

And a quick Google reveals all;

The first example in the Wikipedia article is pretty much a textbook case of what you are looking for;

http://en.wikipedia.org/wiki/Umpolung

lybra0076 - 29-9-2010 at 09:38

=P haha, ok, that helps a lot. I guess I tend to disregard wiki sites...

ScienceSquirrel - 29-9-2010 at 12:53

I think you have to use Wikipedia chemistry with caution and check the references.
There are poor pages but there many excellent pages with good examples and references and this is one of them.
There is enough to grasp the concept and more with a lot of leads in to original papers and reviews.
Really you could start with this page, look up the reference articles, add examples and mechanisms, and come out with an essay that would get an excellent grade for undergraduate work.

[Edited on 29-9-2010 by ScienceSquirrel]