Textbook Question
Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.
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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 38b
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 38bChapter 16, Problem 38b
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
b. isohexylamine
Verified step by step guidance1
Identify the structure of isohexylamine. Isohexylamine is a primary amine with the structure CH3-CH2-CH(CH3)-CH2-CH2-NH2. This means the alkyl group attached to the amine is isohexyl (CH3-CH2-CH(CH3)-CH2-CH2-).
Recall the Gabriel synthesis mechanism. In this method, a phthalimide anion reacts with an alkyl halide to form an N-alkylphthalimide intermediate. This intermediate is then hydrolyzed to release the primary amine.
Determine the alkyl bromide needed. The alkyl bromide should have the same carbon skeleton as the desired amine, but with a bromine atom replacing the amine group. For isohexylamine, the corresponding alkyl bromide would be CH3-CH2-CH(CH3)-CH2-CH2-Br.
Write the reaction sequence. The phthalimide anion (generated by treating phthalimide with a strong base like KOH) reacts with the isohexyl bromide (CH3-CH2-CH(CH3)-CH2-CH2-Br) to form N-isohexylphthalimide.
Explain the final step. The N-isohexylphthalimide is hydrolyzed (using aqueous acid or base) to release isohexylamine (CH3-CH2-CH(CH3)-CH2-CH2-NH2) and phthalic acid as a byproduct.
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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 used to prepare primary amines from alkyl halides. It involves the use of phthalimide, which is first converted to an N-alkyl phthalimide through nucleophilic substitution with an alkyl halide. The resulting N-alkyl phthalimide is then hydrolyzed to yield the primary amine, making this method particularly useful for avoiding the formation of secondary or tertiary amines.
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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 alkylating agents in organic synthesis due to their ability to undergo nucleophilic substitution reactions. The choice of alkyl bromide in Gabriel synthesis is crucial, as it determines the structure of the resulting amine, in this case, isohexylamine.
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Isohexylamine Structure
Isohexylamine is a primary amine with the chemical structure C6H15N, specifically 2-amino-2-methylpentane. Understanding its structure is essential for selecting the appropriate alkyl bromide in Gabriel synthesis. The synthesis requires an alkyl bromide that can provide the correct carbon skeleton, which in this case would be derived from a suitable precursor that leads to the isohexyl group.
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Related Practice
Textbook Question
Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed hydrolysis:
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
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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