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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.

Aspartame Molecule (Source: Wikipedia - Aspartame)

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    $\begingroup$ 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. $\endgroup$
    – Buttonwood
    Jun 10 '17 at 23:58
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Since aspartame is made up of phenylalanine and aspartic acid, upon hydrolysis it will break into corresponding amino acids. But in basic or acidic medium, it generates methanol. According to Wikipedia article of aspartame:

Aspartame is a methyl ester of the dipeptide of the natural amino acids L-aspartic acid and L-phenylalanine. Under strongly acidic or alkaline conditions, aspartame may generate methanol by hydrolysis. Under more severe conditions, the peptide bonds are also hydrolyzed, resulting in free amino acids

Since this is more or less a HW question, I am not going to answer the 2nd part of question. Type - "peptide bond hydrolysis mechanism" in Google and you will get your answer.

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Firstly, find the types of functional groups present in the given compound and then use the theory of hydrolysis of the functional groups. Here functional groups are ester and amide. Finally, use the special characteristic of alpha amino acids.

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