Textbook Question
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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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 7
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 7Chapter 16, Problem 7
What reagent should be used to carry out the following reaction?
Verified step by step guidance1
Analyze the starting material and product: The starting material contains a phenol group (-OH attached to a benzene ring) and an ester functional group. The product shows that the phenol group has been converted into an ester group, indicating an esterification reaction.
Identify the type of reaction: The transformation involves converting the phenol group into an ester. This typically requires a carboxylic acid derivative (such as an acid chloride or anhydride) or a carboxylic acid in the presence of a catalyst.
Select the reagent: To form the ester, an appropriate reagent such as ethyl chloroformate (an acid chloride) or ethyl acetate (a carboxylic acid) can be used. A base like pyridine or triethylamine may be required to neutralize the acidic byproducts.
Consider reaction conditions: The reaction may require mild heating or stirring to ensure the phenol reacts efficiently with the chosen reagent. Solvents like dichloromethane or toluene are commonly used for esterification reactions.
Verify the product: Ensure that the reagent chosen introduces the ethyl group (-CH2CH3) into the ester functional group, as seen in the product structure.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Acyl Substitution
Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. This reaction is common in carboxylic acid derivatives, such as esters and amides, and is characterized by the formation of a tetrahedral intermediate. The reaction typically proceeds with the loss of a leaving group, such as water or an alcohol, resulting in the formation of a new carbonyl compound.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Reagents for Nucleophilic Acyl Substitution
The choice of reagent in nucleophilic acyl substitution is crucial for determining the outcome of the reaction. Common nucleophiles include alcohols, amines, and thiols, which can react with acyl compounds to form esters, amides, or thioesters, respectively. The reaction conditions, such as the presence of acid or base catalysts, can also influence the reactivity of the nucleophile and the efficiency of the substitution process.
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Mechanism of the Reaction
Understanding the mechanism of nucleophilic acyl substitution is essential for predicting the products of the reaction. The mechanism involves the nucleophile attacking the electrophilic carbonyl carbon, forming a tetrahedral intermediate, which then collapses to expel the leaving group and regenerate the carbonyl. This stepwise process highlights the importance of the stability of the leaving group and the nature of the nucleophile in determining the reaction's efficiency and selectivity.
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Related Practice
Textbook Question
Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?
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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? 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
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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