Give a detailed mechanism (show electron flow) for the hydrolysis of cis-norbornene-5,6-endo-dicarboxylic anhydride.

The hydrolysis of cis-norbornene-5,6-endo-dicarboxylic anhydride involves the addition of water to the anhydride functional group, which results in the formation of two carboxylic acid groups. This process can be depicted using the following mechanism: 1. The first step involves the attack of a water molecule on the carbonyl carbon of the anhydride functional group. This results in the formation of a tetrahedral intermediate. 2. The tetrahedral intermediate then collapses, resulting in the cleavage of the anhydride functional group and the formation of a carboxylic acid group. At this stage, the carbonyl oxygen gains a negative charge. 3. The negatively charged oxygen then participates in a proton transfer reaction with a neighboring water molecule, resulting in the formation of a protonated carboxylic acid group and a hydroxide ion. 4. The hydroxide ion then attacks the carbonyl carbon of the remaining anhydride functional group, resulting in the formation of a tetrahedral intermediate. 5. The tetrahedral intermediate again collapses, resulting in the cleavage of the anhydride functional group and the formation of another carboxylic acid group. The carbonyl oxygen again gains a negative charge. 6. Finally, another water molecule participates in a proton transfer reaction with the negatively charged oxygen, resulting in the formation of the second protonated carboxylic acid group and a hydroxide ion. Overall, the hydrolysis of cis-norbornene-5,6-endo-dicarboxylic anhydride involves the sequential addition of water molecules to each of the anhydride functional groups, resulting in the formation of two carboxylic acid groups. The electron flow can be seen in the formation of a tetrahedral intermediate and the transfer of electrons in proton transfer reactions.