Domanda del libro di testo
Predict the product(s) of the following nucleophilic aromatic substitution reactions occurring by the benzyne mechanism.
(b)
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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 46d
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 46dCapitolo 22, Problema 46d
Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.
(d) 
Guida verificata passo dopo passo1
Step 1: Begin with benzene and perform a sulfonation reaction. This involves treating benzene with concentrated sulfuric acid (H2SO4) to introduce a sulfonic acid group (SO3H) onto the benzene ring, forming benzenesulfonic acid.
Step 2: Next, perform a Friedel-Crafts acylation to introduce the acyl group. Use an acyl chloride (such as acetyl chloride, CH3COCl) in the presence of a Lewis acid catalyst like aluminum chloride (AlCl3) to add the acyl group to the benzene ring. This will result in the formation of an acylated benzene derivative.
Step 3: Finally, carry out a bromination reaction. Treat the acylated benzene with bromine (Br2) in the presence of a catalyst such as iron(III) bromide (FeBr3) to introduce a bromine atom onto the benzene ring. The bromine will preferentially add to the position ortho to the acyl group due to the directing effects of the substituents already present on the ring.
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Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for introducing substituents like bromine, sulfonic acid, and carboxylic acid groups onto benzene. Understanding the directing effects of existing substituents is essential for predicting the position of new groups.
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03:07
EAS Review
Directing Effects of Substituents
Substituents on a benzene ring influence the position of incoming groups during EAS reactions. Activating groups, like -OH or -NH2, direct new substituents to ortho/para positions, while deactivating groups, like -NO2 or -SO3H, direct to the meta position. Recognizing these effects is vital for planning multi-step syntheses, as seen in the synthesis of the given substituted benzene.
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Percorso guidato
2:02Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
Functional Group Interconversion
Functional Group Interconversion involves transforming one functional group into another, a key strategy in organic synthesis. For instance, converting a nitro group to an amine or an alkyl group to a carboxylic acid can be necessary steps in a synthetic route. In the context of the given problem, understanding how to introduce and modify functional groups efficiently is crucial for achieving the target molecule in the specified number of steps.
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02:36Identifying Functional Groups
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