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October 31, 2014

Homework Help: O-Chem 253

Posted by Dmitry on Tuesday, June 8, 2010 at 2:12pm.

I hydrolized the following compound: cis-norbornene-5,6-endo-dicarboxylic anhydride
then took the cis-norborene-5,6-endo-dicarboxylic acid and added H2SO4 to it (warmed it up and cooled it) then added drop by drop water (then I reheated the mixture and crystallized it again).

What is the compound? It was positive for carboxylic acid and also positive for an ester.

The structure of my compound can be found on google images "norbornene dicarboxylic acid"

It's a 2 five member ring (one with C=C bond) and it's connected via triangle of c-c bonds, with CO2H popping out from 2nd ring without C=C bond

When I was looking for answer online for what the compound was someone said that it was "add water across the double bond, open the anhydride, and then form a lactone with the carboxylic acid that is closer to the hydroxide" but I'm still not sure what the structure is and if they are actually correct. I was wondering if it's possible to explain it with arrow pushing mechanism please

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