Textbook Question
b. Explain why the rate of aminolysis of an ester cannot be increased by H+.
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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 25b
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 25bChapter 16, Problem 25b
What products are obtained from the following reactions? b. phenyl acetate + excess ethanol + HCl
Verified step by step guidance1
Step 1: Recognize the type of reaction. This is an acid-catalyzed esterification (Fischer esterification) or transesterification reaction, where phenyl acetate (an ester) reacts with excess ethanol in the presence of an acid catalyst (HCl).
Step 2: Understand the mechanism. In the presence of HCl, the carbonyl oxygen of the ester (phenyl acetate) gets protonated, making the carbonyl carbon more electrophilic and susceptible to nucleophilic attack by ethanol.
Step 3: Identify the nucleophile and electrophile. Ethanol acts as the nucleophile, attacking the electrophilic carbonyl carbon of phenyl acetate, leading to the formation of a tetrahedral intermediate.
Step 4: Follow the reaction pathway. The tetrahedral intermediate undergoes proton transfers and elimination of the leaving group (phenol, C6H5OH), resulting in the formation of a new ester, ethyl acetate (CH3COOCH2CH3).
Step 5: Summarize the products. The reaction produces ethyl acetate (the new ester) and phenol as the byproduct. The excess ethanol ensures the reaction proceeds to completion by shifting the equilibrium toward product formation.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ester Hydrolysis
Ester hydrolysis is a reaction where an ester reacts with water or an alcohol in the presence of an acid or base, leading to the formation of an alcohol and a carboxylic acid. In this case, phenyl acetate undergoes hydrolysis in the presence of excess ethanol and HCl, resulting in the formation of phenol and acetic acid.
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Fischer Esterification
Fischer esterification is a process where a carboxylic acid reacts with an alcohol to form an ester and water, typically catalyzed by an acid. In the context of the given reaction, the excess ethanol can also act as a reactant, potentially leading to the formation of ethyl acetate alongside the hydrolysis products.
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Role of Catalysts in Reactions
Catalysts, such as HCl in this reaction, are substances that increase the rate of a chemical reaction without being consumed in the process. In ester hydrolysis and Fischer esterification, HCl serves to protonate the carbonyl oxygen of the ester, making it more susceptible to nucleophilic attack by water or ethanol, thus facilitating the reaction.
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Related Practice
Textbook Question
Using the mechanism for the acid-catalyzed hydrolysis of an ester as your guide, write the mechanism—showing all the curved arrows—for the acid-catalyzed reaction of acetic acid and methanol to form methyl acetate. Use HB+ and :B to represent the proton-donating and proton-removing species, respectively.
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Textbook Question
Write the mechanism for the acid-catalyzed transesterification of ethyl acetate with methanol.
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Textbook Question
Write the mechanism for the acid-catalyzed reaction of tert-butyl acetate with methanol.
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Textbook Question
What products are formed from the acid-catalyzed hydrolysis of the following esters?
a.
b.
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Textbook Question
Show the mechanism for the acid-catalyzed formation of 23c starting with the product obtained from its hydrolysis.
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