Textbook Question
Give the structure of the repeating units in the polymers that are formed in the reactions of the following compounds.
a.
Ch.17 Carboxylic Acids and Their Derivatives
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 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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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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1:12
Acidic Hydrolysis Concept 1
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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Related Practice
Textbook Question
Identify the functional group in the following compounds and give the structures of the products of hydrolysis for these compounds.
a.
Textbook Question
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
a. Isopropyl benzoate
Textbook Question
Write the formula for the phosphate monoester formed from isopropyl alcohol and phosphoric acid.
Textbook Question
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
b.
Textbook Question
What carboxylic acids and amines result from hydrolysis of the following amides?
a.