Textbook Question
Draw a constitutional isomer for C4H11N containing a 1° amine at a
(a) 1° carbon,
(b) 2° carbon, and
(c) 3° carbon.
Ch. 25 - Amines: Structure, Reactions, and Synthesis
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 24, Problem 25c
Predict the product of the following reactions.
(c) 
Verified step by step guidance1
Identify the type of reaction: The presence of Pd(PPh3)4 and KOt-Bu suggests a Buchwald-Hartwig amination reaction, which is used to form carbon-nitrogen bonds.
Analyze the reactants: The starting materials include a chlorinated furan and a secondary amine. The furan ring is a five-membered aromatic ring containing an oxygen atom, and the amine is diethylamine.
Understand the mechanism: In Buchwald-Hartwig amination, the palladium catalyst facilitates the coupling of the aryl halide (chlorinated furan) with the amine. The base (KOt-Bu) deprotonates the amine, making it a better nucleophile.
Predict the product: The nitrogen atom of the deprotonated amine will attack the carbon atom bonded to the chlorine in the furan ring, resulting in the formation of a new C-N bond and the release of a chloride ion.
Consider the regioselectivity: Since the reaction involves a single chlorinated position on the furan, the amine will substitute at this position, leading to the formation of an N-aryl amine product with the furan ring intact.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Palladium-Catalyzed Cross-Coupling Reactions
Palladium-catalyzed cross-coupling reactions are a class of reactions that form carbon-carbon or carbon-heteroatom bonds using a palladium catalyst. In this reaction, Pd(PPh3)4 is used to facilitate the coupling between an aryl halide and an amine, leading to the formation of a new C-N bond. This process is crucial in organic synthesis for constructing complex molecules efficiently.
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Cross-Coupling Reaction Mechanisms
Buchwald-Hartwig Amination
The Buchwald-Hartwig amination is a specific type of palladium-catalyzed cross-coupling reaction where an amine is coupled with an aryl halide to form an aryl amine. This reaction typically requires a palladium catalyst, a ligand, and a base. In the given reaction, the amine is introduced to the chlorinated aromatic compound, resulting in the substitution of the chlorine atom with the amine group.
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Role of Base in Cross-Coupling Reactions
Bases play a critical role in cross-coupling reactions by deprotonating the amine, which enhances its nucleophilicity, allowing it to effectively attack the aryl halide. In this reaction, KOt-Bu (potassium tert-butoxide) serves as the base, facilitating the formation of the C-N bond by activating the amine and stabilizing the palladium complex during the catalytic cycle.
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Related Practice
Textbook Question
We usually calculate Keq for acid–base reactions using pKa values.
(a) Derive an equation to calculate Keq using pKb values, then
(b) use it to calculate the equilibrium constant for the following reaction.
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Textbook Question
Which would you expect to be a stronger nucleophile, ethyl amine or diethyl amine? Why?
Textbook Question
The nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?
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Textbook Question
Following a LiAlH₄ reduction, an IR spectrum suggested that the product was a mixture of the starting amide and the desired amine.
(b) Once separated, how could you distinguish between the amide and the amine using IR spectroscopy?
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Textbook Question
Given the starting reactant, suggest a method for synthesizing the amine on the right.
(b)
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