Textbook Question
Show how you would accomplish the following synthetic conversions.
(c) pentanoic acid → pentan-1-amine
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 19, Problem 30a
Show how you would accomplish the following synthetic conversions.
(a) benzyl bromide → benzylamine
Verified step by step guidance1
Identify the functional group transformation: The conversion involves replacing the bromine atom in benzyl bromide with an amine group (-NH2), which is a nucleophilic substitution reaction.
Choose an appropriate nucleophile: Ammonia (NH3) is a good nucleophile for this reaction, as it can replace the bromine atom to form benzylamine.
Select the reaction conditions: Use an excess of ammonia in a polar solvent like ethanol to promote the substitution reaction. This ensures that the nucleophilic substitution proceeds efficiently.
Write the reaction mechanism: The reaction proceeds via an SN2 mechanism, where the nucleophile (NH3) attacks the carbon atom bonded to the bromine, displacing the bromine atom as a leaving group. The reaction can be represented as:
Isolate and purify the product: After the reaction is complete, the benzylamine product can be separated from the reaction mixture by techniques such as extraction, followed by purification using distillation or recrystallization.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the conversion of benzyl bromide to benzylamine, the bromine atom acts as the leaving group, while the amine (NH2) serves as the nucleophile. Understanding this mechanism is crucial for predicting the outcome of the reaction.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Reactivity of Alkyl Halides
Alkyl halides, such as benzyl bromide, are compounds where a halogen atom is bonded to an alkyl group. The reactivity of these compounds is influenced by the nature of the halogen and the structure of the alkyl group. Benzyl bromide is particularly reactive due to the stability of the resulting carbocation during the nucleophilic substitution process, making it a suitable substrate for conversion to benzylamine.
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Amine Nucleophilicity
Amines are organic compounds that contain a nitrogen atom bonded to hydrogen and/or carbon atoms. They are known for their nucleophilic properties, meaning they can donate a pair of electrons to form a bond with an electrophile. In the context of synthesizing benzylamine from benzyl bromide, the amine's nucleophilicity is essential for effectively attacking the electrophilic carbon in the alkyl halide, facilitating the substitution reaction.
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Related Practice
Textbook Question
Show how Gabriel syntheses are used to prepare the following amines.
(a) benzylamine
(b) hexan-1-amine
(c) γ-aminobutyric acid
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(d) pentanoic acid → hexan-1-amine
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(b) 1-bromo-2-phenylethane → 3-phenylpropan-1-amine
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Textbook Question
Addition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-amine, some dialkylamine, some trialkylamine, and even some tetraalkylammonium bromide.
(a) Give a mechanism to show how this reaction takes place, as far as the dialkylamine.
(b) How would you modify the procedure to get an acceptable yield of heptan-1-amine?
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Textbook Question
Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.
(a) N-butylpiperidine from piperidine
(b) N-benzylaniline from aniline
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