Textbook Question
What reagent should be used to carry out the following reaction?
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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 7b
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 7bChapter 16, Problem 7b
b. What is the product of the reaction of acetamide with HO−? The pKa of NH3 is 36; the pKa of H2O is 15.7.
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Identify the functional group in acetamide. Acetamide contains an amide functional group, which is characterized by a carbonyl group (C=O) directly bonded to a nitrogen atom (−NH2).
Understand the role of HO⁻ (hydroxide ion) in the reaction. HO⁻ is a strong base and can deprotonate acidic protons or participate in nucleophilic attack.
Compare the pKa values provided. The pKa of NH3 is 36, and the pKa of H2O is 15.7. Since the pKa of H2O is much lower, it indicates that water is a stronger acid than NH3. This means that the hydroxide ion (conjugate base of H2O) is unlikely to abstract a proton from NH3 (conjugate acid of the amide nitrogen).
Analyze the reaction mechanism. In the presence of HO⁻, the hydroxide ion can attack the carbonyl carbon of the amide group. This is because the carbonyl carbon is electrophilic due to the partial positive charge created by the electronegativity of the oxygen atom.
Predict the product. The nucleophilic attack by HO⁻ on the carbonyl carbon will lead to the cleavage of the C−N bond, resulting in the formation of a carboxylate ion (CH3COO⁻) and ammonia (NH3) as the products of the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetamide Structure and Reactivity
Acetamide is an amide derived from acetic acid, featuring a carbonyl group (C=O) bonded to a nitrogen atom (N). Its structure influences its reactivity, particularly in nucleophilic and electrophilic reactions. Understanding how acetamide behaves in the presence of strong bases, like hydroxide ions (HO−), is crucial for predicting the outcome of the reaction.
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Reactivity of Molecules
Acid-Base Chemistry and pKa Values
The pKa value indicates the strength of an acid in solution; lower pKa values correspond to stronger acids. In this context, the pKa of NH3 (36) suggests it is a very weak acid, while H2O (pKa 15.7) is a much stronger acid. This information is essential for determining the direction of the reaction between acetamide and hydroxide ions, as it helps predict which species will donate or accept protons.
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Nucleophilic Attack and Deprotonation
In the reaction of acetamide with hydroxide ions, the hydroxide acts as a strong nucleophile, attacking the carbonyl carbon of acetamide. This leads to the formation of a tetrahedral intermediate, which can subsequently undergo deprotonation. Understanding this mechanism is key to predicting the final product of the reaction, which typically results in the formation of an amine and a hydroxyl group.
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Related Practice
Textbook Question
What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? b. a weaker base than the substituent that is attached to the acyl group
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Textbook Question
What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? a. a stronger base than the substituent that is attached to the acyl group
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Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
c.
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Textbook Question
There are three carbon–oxygen bonds in methyl acetate.
a. What are their relative bond lengths?
b. What are the relative infrared (IR) stretching frequencies of these bonds?
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Textbook Question
Which is a correct statement?
A. The delocalization energy of an ester is about 18 kcal/mol, and the delocalization energy of an amide is about 10 kcal/mol.
B. The delocalization energy of an ester is about 10 kcal/mol, and the delocalization energy of an amide is about 18 kcal/mol.
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