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N-Acetylglucosamine (also known as NAG) is an important component on the surfaces of cells.
b. Draw the structures of the products of acid hydrolysis.
16. Carboxylic Acids and Their Derivatives
Amide Hydrolysis
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Determine the nitrogen product formed when the following amide undergoes acidic hydrolysis.
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Verified step by step guidance1
Identify the functional group in the given compound. The structure shows an amide group, which is characterized by a carbonyl group (C=O) directly attached to a nitrogen atom (N).
Understand the reaction conditions. The problem states that the amide undergoes acidic hydrolysis, which typically involves the use of an acid (HCl in this case) and heat to break the amide bond.
During acidic hydrolysis, the amide bond is cleaved, resulting in the formation of a carboxylic acid and an amine or ammonia. The carbonyl carbon of the amide becomes part of the carboxylic acid, while the nitrogen becomes part of the amine.
Examine the structure of the amide. The nitrogen atom is part of a pyrrolidine ring (a five-membered ring containing nitrogen). Upon hydrolysis, this nitrogen will be released as a primary amine.
Predict the nitrogen-containing product. The nitrogen from the pyrrolidine ring will gain a hydrogen ion (H+) from the acidic environment, forming pyrrolidinium ion, which is the protonated form of pyrrolidine.
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