Domanda del libro di testo
Predict the major product of the following electrophilic aromatic substitution reactions.
(c)
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Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases/Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 39
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 39Capitolo 22, Problema 39
With a small electron-donating group on the ring, it is possible to get as much as a 2:1 ratio of ortho to para. Why might this be?
Guida verificata passo dopo passo1
Identify the electron-donating group on the benzene ring. In this case, the methyl group (CH₃) is the electron-donating group.
Understand that electron-donating groups activate the benzene ring towards electrophilic aromatic substitution, making the ortho and para positions more reactive.
Recognize that the ortho position is sterically hindered compared to the para position, but the methyl group is small, reducing steric hindrance and allowing for significant ortho substitution.
Consider the resonance effect: the electron-donating group increases electron density at the ortho and para positions, stabilizing the carbocation intermediate formed during the reaction.
Conclude that the combination of electronic effects (activation and resonance stabilization) and reduced steric hindrance leads to a higher ratio of ortho to para substitution, resulting in the observed 2:1 ratio.
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Concetti chiave
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Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the presence of a catalyst like FeCl3, chlorine acts as the electrophile, attacking the benzene ring. The position of substitution is influenced by existing substituents on the ring, which can direct the incoming group to ortho, meta, or para positions.
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03:07
EAS Review
Ortho/Para Directing Groups
Ortho/para directing groups are substituents on an aromatic ring that increase the electron density at the ortho and para positions, making them more reactive to electrophilic attack. Electron-donating groups, such as alkyl groups, stabilize the carbocation intermediate formed during EAS, favoring substitution at these positions. This explains the higher ratio of ortho to para products in the presence of such groups.
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04:42Ortho, Para major products
Steric and Electronic Effects
Steric and electronic effects influence the distribution of substitution products in EAS. Small electron-donating groups, like methyl, enhance electron density at ortho and para positions, but steric hindrance is less at the para position. However, the ortho position can still be favored due to proximity effects and resonance stabilization, leading to a 2:1 ortho to para product ratio.
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02:53Understanding steric effects.
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