Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
c. benzylamine
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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 43a
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 43aChapter 16, Problem 43a
Propose a mechanism for the reaction of acetic anhydride with water.
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Identify the functional groups in acetic anhydride. Acetic anhydride contains two acyl groups (R-C(=O)-) connected by an oxygen atom. It is a reactive compound that can undergo hydrolysis in the presence of water.
Recognize the nucleophile and electrophile. In this reaction, water acts as the nucleophile (electron-rich species) due to the lone pairs on oxygen, and the carbonyl carbon in acetic anhydride acts as the electrophile (electron-deficient species) due to the partial positive charge on the carbon.
Initiate the reaction by having the nucleophilic oxygen atom of water attack one of the carbonyl carbons in acetic anhydride. This forms a tetrahedral intermediate where the carbonyl oxygen becomes negatively charged.
Stabilize the tetrahedral intermediate by proton transfer. A proton from the water molecule can transfer to the leaving group (the oxygen atom bridging the two acyl groups), facilitating the cleavage of the bond between the carbonyl carbon and the bridging oxygen.
Conclude the mechanism by forming the final products. The reaction results in the formation of two molecules of acetic acid (CH₃COOH) as the acetic anhydride is hydrolyzed by water.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetic Anhydride Structure and Reactivity
Acetic anhydride is a reactive organic compound derived from acetic acid, characterized by its anhydride functional group. Its structure consists of two acetyl groups connected by an oxygen atom, making it a good electrophile. This reactivity allows it to readily undergo hydrolysis when exposed to water, leading to the formation of acetic acid.
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Anhydride Nomenclature
Nucleophilic Attack
In organic chemistry, a nucleophilic attack occurs when a nucleophile, which is a species with a high electron density, attacks an electrophile, which is electron-deficient. In the case of acetic anhydride reacting with water, the oxygen atom in water acts as a nucleophile, attacking the carbonyl carbon of the anhydride. This step is crucial for the hydrolysis mechanism.
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08:27Nucleophilic Addition
Hydrolysis Reaction Mechanism
Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of acetic anhydride, the hydrolysis mechanism involves the nucleophilic attack by water, leading to the formation of a tetrahedral intermediate, which subsequently collapses to yield two molecules of acetic acid. Understanding this mechanism is essential for predicting the products of the reaction.
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Related Practice
Textbook Question
Propose a mechanism for the formation of succinic anhydride from succinic acid in the presence of acetic anhydride at neutral pH.
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Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
d. cyclohexylamine
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Textbook Question
How does acetic anhydride make it easier to form the anhydride?
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Textbook Question
We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrahedral intermediate eliminate the carboxylate ion even if it does not lose a proton before the elimination step? Explain.
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Textbook Question
Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?
a. butyric acid
b. isovaleric acid
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