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 30f
Show how you would accomplish the following synthetic conversions.
(f) (R)-2-bromobutane → (S)-2-methylbutan-1-amine
Verified step by step guidance1
Step 1: Analyze the starting material (R)-2-bromobutane and the target product (S)-2-methylbutan-1-amine. Note that the stereochemistry changes from (R) to (S), and the functional group changes from a bromine atom to a primary amine (-CH2NH2).
Step 2: Perform a nucleophilic substitution reaction (SN2) using cyanide ion (CN⁻) as the nucleophile. This will replace the bromine atom with a cyano group (-CN) and invert the stereochemistry, converting (R)-2-bromobutane to (S)-2-methylbutanenitrile.
Step 3: Reduce the nitrile group (-CN) in (S)-2-methylbutanenitrile to a primary amine (-CH2NH2). This can be accomplished using a reducing agent such as lithium aluminum hydride (LiAlH4) followed by hydrolysis.
Step 4: Verify that the stereochemistry remains (S) after the reduction step, as the reduction of the nitrile group does not affect the stereocenter.
Step 5: Confirm the final product is (S)-2-methylbutan-1-amine, ensuring both the functional group transformation and stereochemical inversion are correct.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In this question, the conversion involves changing the configuration of (R)-2-bromobutane to (S)-2-methylbutan-1-amine, highlighting the importance of understanding chirality and how reactions can lead to the formation of specific stereoisomers.
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Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group (in this case, bromine) by a nucleophile (the amine group). This type of reaction is crucial for the conversion of (R)-2-bromobutane to (S)-2-methylbutan-1-amine, as it demonstrates how nucleophiles can attack electrophilic centers in organic molecules, leading to the formation of new compounds.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Chirality and Inversion of Configuration
Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of a chiral center. In this conversion, the inversion of configuration is significant as the reaction must not only replace the bromine atom but also ensure that the resulting amine has the opposite configuration, transforming (R) to (S) through a specific reaction pathway.
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Related Practice
Textbook Question
For each compound,
(1) classify the nitrogen-containing functional groups.
(2) provide an acceptable name.
(a)
(b)
(c)
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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.
(e) (R)-2-bromobutane → (S)-butan-2-amine
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Textbook Question
Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.
(d) m-aminobenzoic acid
Textbook Question
Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.
(a) aniline
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