Textbook Question
Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.
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Ch. 20 - Carboxylic Acids
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 20, Problem 18b
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(b) 
Verified step by step guidance1
Step 1: Identify the target compound, acetanilide, which is an amide formed from the reaction between a carboxylic acid derivative and an amine. The structure contains an acetamide group (-CONH-) attached to a phenyl ring.
Step 2: Select the appropriate carboxylic acid derivative. In this case, acetic acid (CH₃COOH) or its derivative, such as acetic anhydride (CH₃CO)₂O, can be used as the source of the acetyl group (-COCH₃).
Step 3: Choose the amine required for the synthesis. Aniline (C₆H₅NH₂), which contains a phenyl group attached to an amino group (-NH₂), is the appropriate amine for this reaction.
Step 4: Perform the reaction. React aniline (C₆H₅NH₂) with acetic anhydride (CH₃CO)₂O under mild conditions. The acetic anhydride will transfer the acetyl group to the amine, forming acetanilide and acetic acid as a byproduct.
Step 5: Purify the product. After the reaction, isolate acetanilide by recrystallization or other purification techniques to obtain the pure compound.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acids
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are important in organic synthesis as they can react with amines to form amides. Understanding the reactivity and properties of carboxylic acids is crucial for synthesizing compounds like acetanilide, where a carboxylic acid is used to introduce the carbonyl functionality.
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Carboxylic Acids Nomenclature
Amines
Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles in chemical reactions, making them essential in the formation of amides. In the synthesis of acetanilide, an amine (aniline) reacts with an acyl chloride or carboxylic acid to form the desired product, highlighting the role of amines in organic synthesis.
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Amide Formation
Amide formation is a key reaction in organic chemistry where a carboxylic acid reacts with an amine to produce an amide and water. This reaction is fundamental in the synthesis of various organic compounds, including pharmaceuticals. In the case of acetanilide, the reaction between acetic acid and aniline exemplifies this process, showcasing how functional groups can be transformed to create more complex molecules.
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Related Practice
Textbook Question
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(a)
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Textbook Question
(b) Finish the solution for Solved Problem 20-1 by providing a mechanism for the acid-catalyzed hydrolysis of ethyl formate.
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Textbook Question
The given was missing some important resonance forms of the intermediates shown in brackets. Complete this mechanism by drawing all the resonance forms of these intermediates. Do your resonance forms help to explain why this reaction occurs under very mild conditions (water with a tiny trace of acid)?
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Textbook Question
Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.
(c)
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