Textbook Question
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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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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
Chapter 19, Problem 32
What product is formed from the reaction of p-methylphenol with benzenediazonium chloride?
Verified step by step guidance1
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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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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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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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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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Related Practice
Textbook Question
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.
b. methyl orange
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Textbook Question
Show how the following compounds can be synthesized from benzene:
d. m-methylnitrobenzene
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Textbook Question
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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Textbook Question
Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?
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Textbook Question
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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