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Why isn’t FeBr3 used as a catalyst in the first step of the synthesis of 1,3,5-tribromobenzene?
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 32
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 32Capitolo 18, Problema 32
What product is formed from the reaction of p-methylphenol with benzenediazonium chloride?
Guida verificata passo dopo passo1
Step 1: Recognize the type of reaction. This is an example of an electrophilic aromatic substitution reaction, specifically a diazo coupling reaction, where benzenediazonium chloride acts as an electrophile and p-methylphenol acts as a nucleophile.
Step 2: Identify the reactive site on p-methylphenol. The hydroxyl (-OH) group on the phenol ring is an activating group that increases electron density on the aromatic ring, especially at the ortho and para positions relative to the -OH group. Since the methyl group is already at the para position, the coupling will likely occur at the ortho position.
Step 3: Understand the mechanism. The diazonium ion (N≡N⁺) from benzenediazonium chloride attacks the electron-rich ortho position of p-methylphenol, forming a new bond between the aromatic ring of p-methylphenol and the diazonium group.
Step 4: Consider resonance stabilization. The resulting product will have conjugation between the aromatic ring and the azo (-N=N-) group, which stabilizes the molecule. This conjugation is responsible for the vibrant colors of azo compounds.
Step 5: Name the product. The final product is an azo compound, specifically 2-(p-methylphenylazo)-p-methylphenol, where the azo group (-N=N-) connects the p-methylphenol and the benzene ring from benzenediazonium chloride.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this context, benzenediazonium chloride acts as the electrophile, which can react with the electron-rich p-methylphenol, leading to the substitution of a hydrogen atom on the aromatic ring.
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03:07
EAS Review
Aromatic Compounds
Aromatic compounds are a class of cyclic compounds characterized by their stable ring structure and delocalized π-electrons. p-Methylphenol, also known as p-cresol, is an aromatic compound that contains a hydroxyl group (-OH) and a methyl group (-CH3) attached to a benzene ring, influencing its reactivity in electrophilic substitution reactions.
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08:19Intro to Aromaticity
Diazonium Salts
Diazonium salts are highly reactive intermediates in organic synthesis, formed by the reaction of primary aromatic amines with nitrous acid. Benzenediazonium chloride is a common diazonium salt that can participate in various coupling reactions, including those with aromatic compounds like p-methylphenol, resulting in the formation of azo compounds.
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Percorso guidato
4:54Review of Nitriles Example 5
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Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.
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Show how the following compounds can be synthesized from benzene:
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In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?
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Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?
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Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.
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