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Topic: Lactonization of cis-norbornene-5,6,-dicarboxylic acid  (Read 3774 times)

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Offline greenhornnub

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Lactonization of cis-norbornene-5,6,-dicarboxylic acid
« on: March 30, 2011, 11:32:55 PM »
When cis-norbornene-5,6,-dicarboxylic acid is treated with H2SO4 (water is present), I believe a dehydration occurs and water attacks the double bond opening up the anhydride.  The COOH (closer to the new hydroxide) reaches over and forms a 5 member lactone (gamma).

First, please correct any errors I committed above.  Second, what is the name of the compound formed when H2SO4 contacts cis-norbornene-5,6,-dicarboxylic acid? This product is a structural isomer of cis-norbornene-5,6,-dicarboxylic acid, so the formula is C9 H10 O4, 182.17 grams, and the melting point is 203 celsius

Also, if someone could draft up a mechanism complete with arrow pushing; I would be able to confirm my mechanism.  I would also be infinitely happy.

Thanks for any help offered.

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