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Topic: 2 Carboxyl Groups on Adjacent Carbons?  (Read 5369 times)

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organoman

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2 Carboxyl Groups on Adjacent Carbons?
« on: November 23, 2005, 03:46:02 PM »
I've been given two reactants (a diene and a larger dienophile) in acidic conditions and decided to use a Diels Alder mechanism.  Anyway, my product is a cylcohexene with 2 carboxyl groups, one on the 4 and the other on the 5 carbon (C8H10O4).

My first question is what is this molecules's name (systematic or common)?  I've tried searching goolge for 4,5-dicarboxyl-cyclohexene, 4,5-dicarboxyl-1-cyclohexene, 4,5-dicarboxylic-cyclohexene, and 4,5-dicarboxylic-1-cyclohexene, but have gotten no hits.

My second question is would this molecule be stable with the Oxygens of the carboxyl groups so close to one another?

I would prefer not to post the exact starting materials, this is an assignment and I just want to know if my product is stable and what its name is.  Thanks a lot.

Also, is there any program that could give me the NMR spectrum of an inputed molecule?

Offline FeLiXe

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Re:2 Carboxyl Groups on Adjacent Carbons?
« Reply #1 on: November 23, 2005, 05:29:26 PM »
how about 1,2-Dicarboxyl-4-cyclohexene?

the carboxylic part is like butane-diacid. that's stable. you might get the cyclic intramolecular anhydride though
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organoman

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Re:2 Carboxyl Groups on Adjacent Carbons?
« Reply #2 on: November 23, 2005, 06:44:02 PM »
Thank you for responding.

Wouldn't the acidic conditions prevent the cyclic intramolecular anhydride from forming?  I was considering the same thing but I figured it wouldn't since the final molecule had to maintain the same formula - C8H10O4.

Offline AWK

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Re:2 Carboxyl Groups on Adjacent Carbons?
« Reply #3 on: November 25, 2005, 03:10:51 AM »
search under:
4-cyclohexene-1,2-dicarboxylic acid
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Offline Albert

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Re:2 Carboxyl Groups on Adjacent Carbons?
« Reply #4 on: November 25, 2005, 06:16:33 AM »
Also, is there any program that could give me the NMR spectrum of an inputed molecule?
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