Textbook Question
Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.
1
views
Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 38a
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblem 38aChapter 16, Problem 38a
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
a. pentylamine
Verified step by step guidance1
Understand the Gabriel synthesis: It is a method used to prepare primary amines by reacting a phthalimide anion with an alkyl halide, followed by hydrolysis or hydrazinolysis to release the amine.
Identify the target amine: The target amine in this case is pentylamine, which has the structure CH3-(CH2)4-NH2. This is a primary amine with a five-carbon chain.
Determine the alkyl bromide needed: In the Gabriel synthesis, the alkyl bromide provides the carbon chain that becomes part of the amine. To form pentylamine, the alkyl bromide must have a five-carbon chain and no functional groups other than the bromine. The structure of the alkyl bromide would be CH3-(CH2)4-Br (1-bromopentane).
Write the reaction sequence: The phthalimide anion (generated by treating phthalimide with a strong base like KOH) reacts with 1-bromopentane in an SN2 reaction to form an N-alkylphthalimide intermediate.
Explain the final step: The N-alkylphthalimide is then hydrolyzed (using aqueous acid or base) or treated with hydrazine to release the primary amine, pentylamine, and regenerate the phthalimide.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
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 process involves the nucleophilic substitution of the alkyl halide with the phthalimide, followed by hydrolysis to yield the desired amine. This method is particularly useful because it avoids the formation of secondary or tertiary amines, ensuring that only primary amines are produced.
Recommended video:
Guided course
04:53
General Reaction
Alkyl Halides
Alkyl halides are organic compounds containing a carbon chain bonded to a halogen atom (such as bromine, chlorine, or iodine). In the context of Gabriel synthesis, the choice of alkyl halide is crucial, as it determines the structure of the resulting amine. The reactivity of the alkyl halide also influences the efficiency of the nucleophilic substitution reaction, with primary alkyl halides being the most favorable for this synthesis.
Recommended video:
Guided course
01:52How to name alkyl halides
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, resulting in the replacement of a leaving group. In Gabriel synthesis, the nucleophile (phthalimide) attacks the carbon of the alkyl halide, leading to the formation of a new carbon-nitrogen bond. Understanding the mechanisms of nucleophilic substitution, including factors that affect reactivity and selectivity, is essential for predicting the outcomes of such reactions.
Recommended video:
Guided course
01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Related Practice
Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
b. isohexylamine
1
views
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
1
views
Textbook Question
Which of the following reactions lead to the formation of an amide?
2
views
Textbook Question
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
d. cyclohexylamine
2
views