Domanda del libro di testo
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
c.
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Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds
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. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblema 33a
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblema 33aCapitolo 19, Problema 33a
a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.
Guida verificata passo dopo passo1
Identify the structure of pyridine-N-oxide. Pyridine-N-oxide is a pyridine ring with an oxygen atom bonded to the nitrogen via a coordinate covalent bond, giving the nitrogen a positive formal charge and the oxygen a negative formal charge.
Recall the concept of resonance. Resonance contributors are alternative Lewis structures that show the delocalization of electrons within a molecule. For pyridine-N-oxide, the negative charge on the oxygen can delocalize into the aromatic ring, enhancing electron density at certain positions.
Draw the resonance contributors for pyridine-N-oxide. Start by moving a lone pair of electrons from the negatively charged oxygen into the N-O bond, which pushes the π-electrons in the ring to different positions. This creates resonance structures where the negative charge is delocalized onto the carbon atoms in the ring.
Compare the resonance contributors of pyridine-N-oxide to those of pyridine. In pyridine, the nitrogen atom does not have a formal positive charge, and the electron density in the ring is lower. In contrast, the resonance contributors of pyridine-N-oxide show increased electron density at specific positions in the ring, making it more reactive toward electrophilic aromatic substitution.
Conclude that the increased electron density in pyridine-N-oxide, as shown by its resonance contributors, makes it more nucleophilic and thus more reactive toward electrophilic aromatic substitution compared to pyridine.
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Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the case of pyridine-N-oxide, resonance contributors can show how the presence of the N-oxide group affects electron density distribution, making certain positions on the aromatic ring more reactive toward electrophiles.
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03:04
Drawing Resonance Structures
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 reactivity of the aromatic compound is influenced by the electron-donating or withdrawing effects of substituents, which can stabilize or destabilize the intermediate formed during the reaction.
Video consigliato:
03:07EAS Review
Electron-Withdrawing Groups
Electron-withdrawing groups (EWGs) are substituents that pull electron density away from the aromatic ring, often increasing the reactivity of the ring toward electrophiles. In pyridine-N-oxide, the oxygen atom of the N-oxide group acts as an EWG, enhancing the electrophilic attack at the ortho and para positions compared to unsubstituted pyridine.
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02:37Donating vs Withdrawing Groups
Pratica correlata
Domanda del libro di testo
The chemical shifts of the C-2 hydrogen in the spectra of pyrrole, pyridine, and pyrrolidine are 2.82 ppm, 6.42 ppm, and 8.50 ppm. Match each heterocycle with its chemical shift.
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Domanda del libro di testo
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
d.
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Domanda del libro di testo
b. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?
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Domanda del libro di testo
Explain why pyrrole (pKa ~ 17) is a much stronger acid than ammonia (pKa = 36).
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Domanda del libro di testo
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
a.
b.
652
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