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Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 17, Problem 24b

What carboxylic acids and amines result from hydrolysis of the following amides?
b. N,N-Dimethyl-p-nitrobenzamide

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1
Identify the functional groups in the given amide. N,N-Dimethyl-p-nitrobenzamide contains an amide group (-CONH-) with two methyl groups attached to the nitrogen atom and a nitro group (-NO₂) attached to the benzene ring in the para position.
Understand the hydrolysis reaction. Hydrolysis of an amide involves breaking the bond between the carbonyl carbon (C=O) and the nitrogen atom (N) in the presence of water, typically under acidic or basic conditions. This reaction produces a carboxylic acid and an amine.
Determine the carboxylic acid product. The carbonyl carbon of the amide becomes part of the carboxylic acid. In this case, the benzene ring with the para-nitro group remains attached to the carboxylic acid, resulting in p-nitrobenzoic acid (C₆H₄(NO₂)-COOH).
Determine the amine product. The nitrogen atom and its attached groups (in this case, two methyl groups) are released as the amine. This results in dimethylamine (CH₃)₂NH.
Summarize the products. The hydrolysis of N,N-Dimethyl-p-nitrobenzamide yields p-nitrobenzoic acid and dimethylamine as the products.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrolysis of Amides

Hydrolysis of amides is a chemical reaction where an amide reacts with water, resulting in the formation of a carboxylic acid and an amine. This process typically requires an acid or base catalyst to facilitate the reaction. In the case of N,N-Dimethyl-p-nitrobenzamide, hydrolysis will yield p-nitrobenzoic acid and N,N-dimethylamine.
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Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are known for their acidic properties and can be derived from the hydrolysis of amides. In this context, the carboxylic acid produced from the hydrolysis of N,N-Dimethyl-p-nitrobenzamide is p-nitrobenzoic acid, which has various applications in organic synthesis.
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Amines

Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as bases and nucleophiles in chemical reactions. In the hydrolysis of N,N-Dimethyl-p-nitrobenzamide, the resulting amine is N,N-dimethylamine, which is a tertiary amine commonly used in various chemical processes and as a solvent.
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