Domanda del libro di testo
One of the following compounds undergoes electrophilic aromatic substitution predominantly at C-3, and one undergoes electrophilic aromatic substitution predominantly at C-4. Which is which?
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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 25
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblema 25Capitolo 19, Problema 25
Rank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction:
Guida verificata passo dopo passo1
Step 1: Understand the concept of electrophilic aromatic substitution (EAS). In EAS, the reactivity of a benzene ring depends on the substituents attached to it. Electron-donating groups (EDGs) activate the ring, making it more reactive, while electron-withdrawing groups (EWGs) deactivate the ring, making it less reactive.
Step 2: Analyze the substituents on each compound. (i) has an ethyl group, which is an electron-donating group via hyperconjugation. (ii) has a methoxy group (-OCH3), which is a strong electron-donating group due to resonance and inductive effects. (iii) has a nitro group (-NO2), which is a strong electron-withdrawing group due to resonance and inductive effects. (iv) has an aldehyde group (-CHO), which is an electron-withdrawing group due to inductive effects.
Step 3: Rank the substituents based on their activating or deactivating effects. Methoxy (-OCH3) is the strongest activator, followed by ethyl (-CH2CH3). Aldehyde (-CHO) is a moderate deactivator, and nitro (-NO2) is the strongest deactivator.
Step 4: Predict the reactivity of the compounds in EAS. The compound with the strongest electron-donating group will be the most reactive, while the compound with the strongest electron-withdrawing group will be the least reactive.
Step 5: Rank the compounds from most reactive to least reactive based on the substituents: (ii) > (i) > (iv) > (iii).
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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 reaction typically involves the formation of a sigma complex, where the aromaticity is temporarily lost, followed by deprotonation to restore aromaticity. Understanding the mechanism and the role of the electrophile is crucial for predicting the reactivity of different aromatic compounds.
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03:07
EAS Review
Activating and Deactivating Groups
In EAS, substituents on the aromatic ring can either activate or deactivate the ring towards further substitution. Activating groups, such as alkyl groups or electron-donating groups (like -OCH3), increase the electron density of the ring, making it more reactive. Conversely, deactivating groups, such as nitro (-NO2) or carbonyl (-C=O) groups, withdraw electron density, reducing reactivity. The nature of these groups significantly influences the order of reactivity in EAS.
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03:27Activating and deactivating groups
Ortho/Para vs. Meta Directing Effects
Substituents on an aromatic ring can also influence the position where new substituents are added during EAS. Ortho and para directing groups favor substitution at the ortho or para positions relative to themselves, while meta directing groups lead to substitution at the meta position. This directing effect is essential for predicting the products of EAS reactions and understanding the overall reactivity of the compounds in the given question.
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04:42Ortho, Para major products
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