# When you hydrolyze asparatame what do you get as a product

On my Organic Chemistry 1 class final, the instructor threw us off with the last question. It asked:

What products would be obtained if asparatame were hydrolyzed completely in an aqueous solution of HCl?
Bonus: Write a proposed mechanism.

I couldn't figure out how to solve this problem because I didn't know which oxygen attacked the hydrogen from HCl.

• Hint: The molecule contains a methyl ester, which will yield (after neutralisation) a carbonic acid, and methanol. At the same time, the molecule contains an amid; its hydrolysis will yield (after neutralisation) a carbonic acid, and an amine. In the special case here, both carbonic acids happens to be $\alpha{}$-amino acids. Jun 10 '17 at 23:58