Textbook Question
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.
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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 77a
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 77aChapter 16, Problem 77a
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.
Verified step by step guidance1
Step 1: Begin by understanding the reaction setup. A carboxylic acid (CH3C=O(OH)) is dissolved in isotopically labeled water (H2O18) in the presence of an acid catalyst (HCl). The goal is to explain how the isotopic label (O18) is incorporated into both oxygen atoms of the carboxylic acid.
Step 2: Recognize that the acid catalyst (HCl) protonates the carboxylic acid, making the carbonyl group more electrophilic. This protonation step is crucial for facilitating subsequent reactions. Represent this step as:
Step 3: After protonation, the carbonyl oxygen becomes positively charged, making the carbonyl carbon more susceptible to nucleophilic attack. The isotopically labeled water (H2O18) acts as a nucleophile and attacks the carbonyl carbon, forming a tetrahedral intermediate. Represent this step as:
Step 4: The tetrahedral intermediate undergoes proton transfer and exchange with the isotopically labeled water (H2O18). This exchange allows the O18 isotope to be incorporated into the hydroxyl group. Represent this step as:
Step 5: Finally, the intermediate undergoes dehydration (loss of water) and reformation of the carbonyl group. During this step, the isotopically labeled oxygen (O18) is incorporated into the carbonyl oxygen. This completes the mechanism, explaining how the O18 isotope is incorporated into both oxygen atoms of the carboxylic acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acid Structure and Reactivity
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). This functional group is polar and can participate in hydrogen bonding, making carboxylic acids relatively acidic. Understanding their structure is crucial for predicting their reactivity, especially in nucleophilic addition reactions where the carbonyl carbon is susceptible to attack by nucleophiles.
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Carboxylic Acids Nomenclature
Isotopic Labeling in Chemical Reactions
Isotopic labeling involves using isotopes, such as oxygen-18 (O-18), to trace the movement of atoms through a chemical reaction. In this context, the incorporation of O-18 into the carboxylic acid indicates that the water molecules are participating in the reaction mechanism. This technique helps chemists understand reaction pathways and mechanisms by tracking how specific atoms are transformed during the reaction.
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Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction, often by protonating a reactant to make it more electrophilic. In the case of carboxylic acids, the addition of an acid catalyst like HCl can facilitate the formation of a more reactive intermediate, allowing for the incorporation of water molecules into the product. This mechanism is essential for understanding how the isotopic label is transferred to the carboxylic acid.
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Related Practice
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
Identify the major and minor products of the following reaction:
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Textbook Question
When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.
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