Textbook Question
Propose a mechanism for the reaction of acetic anhydride with water.
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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 Bonding31
- 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 41a,b
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 41a,bChapter 15, Problem 41a,b
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
Verified step by step guidance1
Identify the structure of the carboxylic acids given in the problem. Butyric acid is a four-carbon carboxylic acid with the formula CH₃CH₂CH₂COOH, and isovaleric acid is a five-carbon branched carboxylic acid with the formula (CH₃)₂CHCH₂COOH.
Understand the reaction sequence. The reaction involves two steps: (1) substitution of the halide in the alkyl halide with a cyanide group (–CN) using sodium cyanide (NaCN), and (2) hydrolysis of the nitrile group (–CN) in acidic aqueous solution to form a carboxylic acid.
Determine the alkyl halide precursor for butyric acid. The nitrile intermediate for butyric acid is CH₃CH₂CH₂CN. To form this nitrile, the corresponding alkyl halide must be CH₃CH₂CH₂Br or CH₃CH₂CH₂Cl, where the halide group is replaced by –CN in the first step.
Determine the alkyl halide precursor for isovaleric acid. The nitrile intermediate for isovaleric acid is (CH₃)₂CHCH₂CN. To form this nitrile, the corresponding alkyl halide must be (CH₃)₂CHCH₂Br or (CH₃)₂CHCH₂Cl, where the halide group is replaced by –CN in the first step.
Summarize the process: For butyric acid, the alkyl halide is CH₃CH₂CH₂X (where X = Br or Cl). For isovaleric acid, the alkyl halide is (CH₃)₂CHCH₂X (where X = Br or Cl). These alkyl halides undergo substitution with NaCN to form nitriles, followed by hydrolysis to yield the carboxylic acids.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkyl Halides
Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are important intermediates in organic synthesis and can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile. Understanding the structure and reactivity of alkyl halides is crucial for predicting the products of reactions involving these compounds.
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Nucleophilic Substitution Reaction
Nucleophilic substitution reactions involve the replacement of a leaving group (like a halogen) by a nucleophile, such as cyanide ions (CN-). This reaction is fundamental in organic chemistry, particularly in the synthesis of carboxylic acids from alkyl halides. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions of the reaction.
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Carboxylic Acid Formation
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). In the context of the question, the reaction of alkyl halides with sodium cyanide followed by hydrolysis in acidic conditions leads to the formation of carboxylic acids. This transformation is significant in organic synthesis, as it allows for the conversion of simpler alkyl halides into more complex carboxylic acids.
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Related Practice
Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
b. isohexylamine
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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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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
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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