Textbook Question
a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 75
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 75Chapter 16, Problem 75
An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product is formed? Explain.
Verified step by step guidance1
Understand the reactivity of amines: Primary and secondary amines have a hydrogen atom attached to the nitrogen, which allows them to act as nucleophiles and react with acyl chlorides to form amides. Tertiary amines, however, lack this hydrogen atom, which makes them unable to form amides in this reaction.
Analyze the reaction mechanism: In the case of primary or secondary amines, the lone pair of electrons on the nitrogen attacks the carbonyl carbon of the acyl chloride, leading to the formation of a tetrahedral intermediate. This intermediate then eliminates HCl to form the amide product.
Consider the case of tertiary amines: Since tertiary amines do not have a hydrogen atom on the nitrogen, they cannot eliminate HCl to form an amide. Instead, they act as bases and react with the HCl produced during the reaction.
Predict the product: When a tertiary amine reacts with an acyl chloride, the tertiary amine typically forms a salt by accepting a proton from the HCl. The product is an ammonium salt, specifically a quaternary ammonium chloride.
Summarize the outcome: For primary and secondary amines, the major product is an amide. For tertiary amines, the reaction does not produce an amide but instead forms a quaternary ammonium salt as the major product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amine Reactivity
Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. Primary and secondary amines have at least one hydrogen atom available for nucleophilic attack, allowing them to react with acyl chlorides to form amides. In contrast, tertiary amines lack this hydrogen, making them unable to form amides through this reaction.
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Reductive Amination
Acyl Chloride
Acyl chlorides, also known as acid chlorides, are reactive compounds containing a carbonyl group (C=O) bonded to a chlorine atom. They are highly electrophilic and readily react with nucleophiles, such as amines, to form amides. The reaction involves the nucleophilic attack of the amine on the carbonyl carbon, leading to the formation of the amide and the release of hydrochloric acid.
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01:57Recognizing acyl chlorides and anhydrides.
Amide Formation
Amides are organic compounds characterized by the presence of a carbonyl group (C=O) directly attached to a nitrogen atom (N). The formation of amides from amines and acyl chlorides is a key reaction in organic chemistry, typically resulting in the substitution of the chlorine atom by the amine. This reaction is significant in synthesizing various pharmaceuticals and agrochemicals, highlighting the importance of understanding the reactivity of different amine types.
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01:33Amide Nomenclature
Related Practice
Textbook Question
When a student treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.
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Textbook Question
a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
c. If an ester is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, where will the label reside in the product?
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Textbook Question
a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethanol. Why? (HINT: Build models.)
b. Would he have encountered the same problem if he had tried to synthesize the methyl ester of 4-methylbenzoic acid in the same way?
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Textbook Question
a. Identify the two products obtained from the following reaction:
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Textbook Question
When butanoic acid and 18O-labeled methanol react under acidic conditions, what compounds are labeled when the reaction has reached equilibrium?
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