Textbook Question
Show how you would accomplish the following synthetic conversions.
(c) pentanoic acid → pentan-1-amine
1
views
Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 29a,b,c
Show how Gabriel syntheses are used to prepare the following amines.
(a) benzylamine
(b) hexan-1-amine
(c) γ-aminobutyric acid
Verified step by step guidance1
Step 1: Understand the Gabriel synthesis. It is a method used to prepare primary amines from alkyl halides. The synthesis involves the use of phthalimide as a precursor, which reacts with an alkyl halide to form an N-alkylphthalimide intermediate. This intermediate is then hydrolyzed to yield the primary amine.
Step 2: For benzylamine (a), start by reacting phthalimide with benzyl bromide (C6H5CH2Br) in the presence of a base like KOH. This forms N-benzylphthalimide. Hydrolyze the intermediate using acid or base to release benzylamine (C6H5CH2NH2).
Step 3: For hexan-1-amine (b), react phthalimide with 1-bromohexane (C6H13Br) under similar conditions to form N-hexylphthalimide. Hydrolyze the intermediate to yield hexan-1-amine (C6H13NH2).
Step 4: For γ-aminobutyric acid (c), react phthalimide with 4-bromobutyric acid (BrCH2CH2CH2COOH). This forms N-(4-carboxybutyl)phthalimide. Hydrolyze the intermediate to yield γ-aminobutyric acid (NH2CH2CH2CH2COOH).
Step 5: Ensure proper reaction conditions for each step, such as using a suitable base for the initial reaction and appropriate hydrolysis conditions (acidic or basic) to cleave the phthalimide and release the desired amine.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
9mWas 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 used to prepare primary amines from phthalimide. The process involves the nucleophilic substitution of the phthalimide with an alkyl halide, followed by hydrolysis to yield the desired amine. This technique is particularly useful for synthesizing amines that are difficult to obtain through other methods, as it avoids the formation of secondary or tertiary amines.
Recommended video:
Guided course
04:53
General Reaction
Amines Structure and Classification
Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They are classified into primary, secondary, and tertiary amines based on the number of carbon-containing groups attached to the nitrogen atom. Understanding the structure of amines is crucial for predicting their reactivity and the products formed during synthesis.
Recommended video:
Guided course
07:17Structural Classification
Functional Group Transformation
Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In the context of amine synthesis, this involves the transformation of starting materials, such as phthalimide and alkyl halides, into amines. Recognizing how different functional groups can be interconverted is essential for designing synthetic pathways in organic chemistry.
Recommended video:
Guided course
02:36Identifying Functional Groups
Related Practice
Textbook Question
Show how to synthesize the following amines from the indicated starting materials by reductive amination.
(e)
7
views
Textbook Question
Show how you would accomplish the following synthetic conversions.
(b) 1-bromo-2-phenylethane → 3-phenylpropan-1-amine
3
views
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?
1
views
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
5
views
Textbook Question
Show how you would accomplish the following synthetic conversions.
(a) benzyl bromide → benzylamine
1
views