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 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 38c
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 38cChapter 16, Problem 38c
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
c. benzylamine
Verified step by step guidance1
Understand the Gabriel synthesis: It is a method used to prepare primary amines by reacting a phthalimide derivative with an alkyl halide, followed by hydrolysis or hydrazinolysis to release the amine.
Identify the target amine: The target amine in this case is benzylamine, which has the structure C₆H₅CH₂NH₂. This means the alkyl group attached to the bromide should be a benzyl group (C₆H₅CH₂).
Determine the required alkyl bromide: In the Gabriel synthesis, the alkyl bromide provides the alkyl group that will eventually become part of the amine. Therefore, the alkyl bromide should be benzyl bromide (C₆H₅CH₂Br).
Write the reaction: The phthalimide anion (generated by treating phthalimide with a strong base) reacts with benzyl bromide (C₆H₅CH₂Br) in an SN2 reaction to form N-benzylphthalimide.
Complete the synthesis: Hydrolyze or treat N-benzylphthalimide with hydrazine to release benzylamine (C₆H₅CH₂NH₂) as the final product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Gabriel Synthesis
Gabriel synthesis is a method for preparing primary amines from alkyl halides using phthalimide as a nucleophile. The reaction involves the nucleophilic substitution of the alkyl halide with the phthalimide, followed by hydrolysis to yield the amine. This method is particularly useful because it avoids the formation of secondary or tertiary amines, ensuring the production of a primary amine.
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Alkyl Bromides
Alkyl bromides are organic compounds containing a bromine atom attached to an alkyl group. They are commonly used as electrophiles in nucleophilic substitution reactions, such as those in Gabriel synthesis. The choice of alkyl bromide is crucial, as it determines the structure of the resulting amine, and in this case, a benzyl bromide would be appropriate for synthesizing benzylamine.
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Benzylamine Structure
Benzylamine is an aromatic amine with the structure C6H5CH2NH2, consisting of a benzene ring attached to a methylene group (–CH2–) and an amino group (–NH2). Understanding its structure is essential for selecting the correct alkyl bromide in Gabriel synthesis. Specifically, benzyl bromide (C6H5CH2Br) would be the alkyl bromide used to produce benzylamine through this synthetic route.
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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
Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed hydrolysis:
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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
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
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Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
a. pentylamine
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