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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 29
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 29Capitolo 18, Problema 29
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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Understand the role of the diazonium group (-N≡N⁺) on a benzene ring. The diazonium group is an electron-withdrawing group due to the positive charge on the nitrogen atom and the triple bond, which pulls electron density away from the benzene ring.
Recall the concept of electrophilic aromatic substitution (EAS). In EAS, the position of substitution is influenced by the electronic effects of substituents already present on the benzene ring. Electron-withdrawing groups typically direct incoming substituents to the meta position, while electron-donating groups direct them to the ortho and para positions.
Analyze the resonance structures of the benzene ring with the diazonium group. The diazonium group does not have resonance structures that stabilize the carbocation intermediate at the meta position during EAS. Instead, it stabilizes the carbocation intermediates at the ortho and para positions through resonance effects.
Recognize that the diazonium group is unique compared to other electron-withdrawing groups. While most electron-withdrawing groups direct substituents to the meta position, the diazonium group stabilizes the ortho and para positions due to its ability to delocalize positive charge through resonance.
Conclude that the diazonium group on a benzene ring cannot direct an incoming substituent to the meta position because it stabilizes the ortho and para positions through resonance effects, making these positions more favorable for substitution.
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Diazonium Group
A diazonium group is a functional group characterized by the presence of a nitrogen atom bonded to a benzene ring, typically represented as -N2+. It is highly reactive and can participate in various electrophilic aromatic substitution reactions. However, its presence on the benzene ring influences the reactivity and orientation of incoming substituents due to its electron-withdrawing nature.
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Sequence Groups
Electrophilic Aromatic Substitution (EAS)
Electrophilic aromatic substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The directing effects of substituents are crucial in determining the position of the incoming electrophile. Substituents can be classified as ortho/para-directing or meta-directing based on their electronic effects, which influence the stability of the intermediate carbocation formed during the reaction.
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Ortho/Para vs. Meta Directing Effects
Substituents on a benzene ring can direct new substituents to specific positions based on their electronic properties. Ortho and para directing groups, such as -OH or -NH2, donate electron density, stabilizing the carbocation intermediate at these positions. In contrast, the diazonium group, being electron-withdrawing, destabilizes the carbocation at the meta position, making it unfavorable for substitution to occur there.
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