Textbook Question
The Gabriel synthesis is most frequently done with 1° alkyl halides. Why is it less successful with more substituted halides?
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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 56b
Suggest reagents to carry out the following transformations. Some may require more than one step.
(b) 
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Identify the starting material and the product. The starting material is 2-bromo-3-methylpyridine, and the product is 2-dimethylamino-3-methylpyridine.
Recognize that the transformation involves replacing the bromine atom with a dimethylamino group. This suggests a nucleophilic substitution reaction.
Consider using a nucleophilic substitution reaction such as the Buchwald-Hartwig amination, which is effective for aryl halides. This reaction typically requires a palladium catalyst, a ligand, and a base.
Select appropriate reagents for the Buchwald-Hartwig amination. A common choice is Pd(OAc)₂ as the catalyst, a phosphine ligand like Xantphos, and a base such as sodium tert-butoxide.
Use dimethylamine as the nucleophile in the reaction. The reaction conditions should facilitate the substitution of the bromine atom with the dimethylamino group, yielding the desired product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Aromatic Substitution
Nucleophilic aromatic substitution involves the replacement of a leaving group, such as bromine, on an aromatic ring with a nucleophile. This reaction is facilitated by electron-withdrawing groups on the ring, which stabilize the intermediate. In this transformation, the bromine is replaced by an amine group, indicating a nucleophilic substitution process.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Amination
Amination is the process of introducing an amine group into a molecule. In this reaction, the brominated aniline undergoes amination to form a substituted aniline. This typically involves the use of reagents like ammonia or amines, often under conditions that promote nucleophilic attack on the aromatic ring.
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Pyridine Ring Chemistry
Pyridine is a basic heterocyclic aromatic organic compound with a nitrogen atom. Its chemistry is influenced by the electron-withdrawing nature of the nitrogen, which affects reactivity and substitution patterns. Understanding pyridine's behavior is crucial for predicting outcomes in reactions involving pyridine derivatives, such as the transformation shown in the image.
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Related Practice
Textbook Question
Predict the product(s) of the reactions shown.
(b)
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Textbook Question
The synthesis of ⍺-hydroxy acids can be done starting with amino acids. Suggest a mechanism of the two-step transformation shown. [The alcohol oxygen is the same in the reactant and product.
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Predict the product(s) of the reactions shown.
(j)
Textbook Question
The final step in the synthesis of diazoxide, a drug used to treat low blood pressure, is shown here. Suggest a mechanism for this step.
Textbook Question
Predict the product(s) of the reactions shown.
(i)
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