Domanda del libro di testo
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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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 25 - Amines: Structure, Reactions, and SynthesisProblema 67
Mullins 1st EditionCh. 25 - Amines: Structure, Reactions, and SynthesisProblema 67Capitolo 24, Problema 67
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.
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Identify the reactants and products: The reactants are a sulfonamide with a chlorine substituent on the benzene ring and acetic anhydride. The product is diazoxide, which has a cyclic structure with a sulfonamide group and a nitrogen-containing ring.
Recognize the functional groups involved: The sulfonamide group (SO2NH2) and the acetic anhydride (CH3CO) are key functional groups. The acetic anhydride is likely to act as an acylating agent.
Consider the nucleophilic attack: The nitrogen atom in the sulfonamide group can act as a nucleophile, attacking the electrophilic carbonyl carbon of the acetic anhydride. This forms a tetrahedral intermediate.
Formation of the cyclic structure: After the nucleophilic attack, the intermediate can undergo intramolecular cyclization. The nitrogen atom can attack the carbonyl carbon of the acetic anhydride, leading to the formation of the cyclic structure present in diazoxide.
Loss of acetic acid: The cyclization step results in the expulsion of acetic acid, completing the formation of the diazoxide structure. This step involves the reformation of the carbonyl group and stabilization of the cyclic product.
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Reaction Mechanisms
A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding mechanisms is crucial for predicting the products and the conditions under which a reaction occurs.
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Heck Reaction Mechanism
Nucleophiles and Electrophiles
Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. In organic reactions, the interaction between nucleophiles and electrophiles is fundamental, as it drives the formation of new bonds and the transformation of reactants into products.
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03:Nucleophile or Electrophile
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying functional groups in a compound is essential for predicting its reactivity and the types of reactions it can undergo, which is particularly important in the synthesis of complex organic compounds like diazoxide.
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02:36Identifying Functional Groups
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