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Ch. 24 - Amino Acids, Peptides, and Proteins
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 24, Problema 29c

Predict the products of the following reactions.
(c) Chemical reaction showing lysine reacting with excess acetic anhydride, indicating a product formation.

Guida verificata passo dopo passo
1
Step 1: Identify the reactants. Lys refers to lysine, an amino acid with an amine group (-NH2) and a carboxylic acid group (-COOH), along with an additional amine group in its side chain. (CH3CO)2O is acetic anhydride, a reagent commonly used for acetylation reactions.
Step 2: Understand the reaction conditions. The presence of excess acetic anhydride suggests that all nucleophilic groups in lysine will react with acetic anhydride to form acetylated products.
Step 3: Determine the reactive sites in lysine. The primary amine group (-NH2) in the side chain and the alpha-amino group (-NH2) attached to the alpha carbon are both nucleophilic and can react with acetic anhydride. Additionally, the hydroxyl group (-OH) of the carboxylic acid can also react.
Step 4: Predict the products. Each amine group will react with acetic anhydride to form an amide bond, resulting in acetylation. The hydroxyl group of the carboxylic acid will react to form an ester bond. The final product will be a fully acetylated lysine derivative.
Step 5: Write the general structure of the product. The alpha-amino group and the side chain amine group will each have an acetyl group (-COCH3) attached, and the carboxylic acid group will be converted into an ester (-COOCH3).

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