Open Question
Identify the functional group in the following compounds and give the structures of the products of hydrolysis for these compounds.
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16. Carboxylic Acids and Their Derivatives
Amide Hydrolysis
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Determine the carboxylate anion formed in the following reaction between the given amide and aqueous base.
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Verified step by step guidance1
Identify the functional group in the given amide. The structure shows an amide group, which consists of a carbonyl group (C=O) directly bonded to a nitrogen atom (N).
Recognize the reaction conditions: the presence of an aqueous base (OH-) and heat. This suggests a hydrolysis reaction, specifically base-catalyzed hydrolysis of the amide.
Understand the mechanism: In base-catalyzed hydrolysis, the hydroxide ion (OH-) attacks the carbonyl carbon of the amide, leading to the formation of a tetrahedral intermediate.
The intermediate collapses, expelling the amine group and forming a carboxylic acid. Under basic conditions, the carboxylic acid deprotonates to form a carboxylate anion.
Examine the structure of the starting amide to determine the resulting carboxylate anion. The carbonyl carbon of the amide becomes the carbonyl carbon of the carboxylate anion, and the rest of the structure remains unchanged except for the conversion of the amide nitrogen to a leaving group.
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