Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained if aspartame is hydrolyzed completely in an aqueous solution of HCl?

Verified step by step guidance

1. Identify the functional groups in the structure of aspartame. Aspartame contains ester groups, amide groups, and a carboxylic acid group. These are susceptible to hydrolysis under acidic conditions.
2. Understand the mechanism of hydrolysis in acidic conditions. Ester groups hydrolyze to form alcohols and carboxylic acids, while amide groups hydrolyze to form carboxylic acids and amines.
3. Focus on the ester bond in aspartame. The ester bond between the phenylalanine residue and the methyl group will hydrolyze to produce methanol and phenylalanine.
4. Examine the amide bond in aspartame. The amide bond between phenylalanine and aspartic acid will hydrolyze to produce phenylalanine and aspartic acid.
5. Combine the products from the hydrolysis reactions. The complete hydrolysis of aspartame in aqueous HCl will yield methanol, phenylalanine, and aspartic acid as the final products.

Key Concepts

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of organic compounds, hydrolysis often involves the cleavage of ester or amide bonds, leading to the formation of acids and alcohols or amines. For aspartame, hydrolysis will break it down into its constituent amino acids and methanol when treated with an acid like HCl.

Aspartame Structure

Aspartame is a dipeptide methyl ester composed of two amino acids: aspartic acid and phenylalanine. Its structure includes an ester bond and a methyl group, which contribute to its sweetness. Understanding its structure is crucial for predicting the products of hydrolysis, as the reaction will yield the free amino acids and methanol upon complete hydrolysis.

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In the case of aspartame hydrolysis in an aqueous HCl solution, the acid facilitates the breakdown of the peptide bond and ester bond, leading to the formation of the products. This concept is essential for understanding how the reaction proceeds and the conditions required for complete hydrolysis.