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 8b
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 8bChapter 16, Problem 8b
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
Verified step by step guidance1
Identify the type of reaction: An acyl substitution reaction involves the replacement of the leaving group attached to the acyl carbon with a nucleophile. The reaction proceeds through a tetrahedral intermediate.
Analyze the leaving group: The stability of the leaving group is determined by its basicity. A weaker base (more stable) is a better leaving group compared to a stronger base (less stable).
Compare the basicity of the new group and the existing substituent: If the new group in the tetrahedral intermediate is a weaker base than the substituent currently attached to the acyl group, it will be more likely to leave during the collapse of the intermediate.
Predict the outcome: Since the new group is a weaker base, it will not replace the existing substituent. Instead, the tetrahedral intermediate will collapse back to the original acyl compound, resulting in no reaction.
Conclude the result: The reaction will not produce a new carboxylic acid derivative or a mixture of derivatives. The starting material remains unchanged because the weaker base cannot displace the stronger base.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acyl Substitution Reaction
An acyl substitution reaction involves the replacement of a leaving group in an acyl compound (like an acyl chloride or an anhydride) with a nucleophile. This process typically results in the formation of a new carboxylic acid derivative. Understanding the mechanism of this reaction is crucial, as it helps predict the outcome based on the nature of the nucleophile and the leaving group.
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Reactions of Amino Acids: Acylation Example 1
Tetrahedral Intermediate
During acyl substitution, a tetrahedral intermediate is formed when the nucleophile attacks the carbonyl carbon of the acyl compound. This intermediate is crucial for determining the fate of the reaction, as it can either collapse back to the starting materials or proceed to form the final product, depending on the stability of the new group attached and the nature of the leaving group.
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04:31Stability of Conjugated Intermediates
Strength of Bases
The strength of the nucleophile (or new group) in the tetrahedral intermediate plays a significant role in the outcome of the acyl substitution reaction. If the new group is a weaker base than the original substituent, it is less likely to displace the leaving group effectively, which can lead to no reaction or the formation of a mixture of products. This concept is essential for predicting the reactivity and selectivity of the reaction.
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Related Practice
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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Textbook Question
Using the pKa values listed in [TABLE 15.1], predict the products of the following reactions:
d.
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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
Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
c.
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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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