Domanda del libro di testo
Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.
1087
views
Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
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
Tutti i libri di testo
Mullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic RingProblema 18d
Mullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic RingProblema 18dCapitolo 23, Problema 18d
Predict the product of the following substitution/addition reactions involving phenoxides. [Because this problem represents a review of current and previous material, section numbers have been provided for your reference.]
(d) 
Guida verificata passo dopo passo1
Step 1: Analyze the reactants. The first reactant is phenol (C6H5OH), which can form phenoxide ions when treated with a strong base like NaOH. The second reactant is 4-bromo-3-nitrobenzoyl chloride, which contains an electrophilic carbonyl group and a bromine atom attached to the aromatic ring.
Step 2: Understand the role of NaOH. NaOH will deprotonate the phenol to form the phenoxide ion (C6H5O⁻), which is a strong nucleophile. This nucleophile can attack electrophilic centers in the second reactant.
Step 3: Identify the electrophilic site in the second reactant. The carbonyl carbon in the benzoyl chloride group is highly electrophilic due to the electron-withdrawing effects of the nitro group and the chlorine atom. This makes it susceptible to nucleophilic attack by the phenoxide ion.
Step 4: Predict the mechanism. The phenoxide ion will attack the carbonyl carbon of the benzoyl chloride group, leading to the formation of a tetrahedral intermediate. The chloride ion (Cl⁻) will then leave, resulting in the formation of an ester bond between the phenoxide and the benzoyl group.
Step 5: Consider the final product. The substitution reaction will yield a compound where the phenoxide group is attached to the benzoyl group, forming an ester. The bromine and nitro groups on the aromatic ring remain unchanged.
Risposta video verificata per un problema simile:
Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Concetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Phenoxide Ion
A phenoxide ion is formed when phenol (C6H5OH) loses a proton (H+) from its hydroxyl group, resulting in a negatively charged ion (C6H5O-). This ion is a strong nucleophile due to the resonance stabilization provided by the aromatic ring, making it highly reactive in substitution and addition reactions.
Video consigliato:
Percorso guidato
3:39
Metal Ion Catalysis Concept 1
Nucleophilic Aromatic Substitution (NAS)
Nucleophilic aromatic substitution is a reaction where a nucleophile replaces a leaving group on an aromatic ring. This process is facilitated by the presence of electron-withdrawing groups, such as nitro (NO2) or halogens, which stabilize the negative charge in the intermediate Meisenheimer complex, allowing the nucleophile to attack the aromatic system.
Video consigliato:
02:10NAS in the addition-elimination pathway
Reactivity of Aromatic Compounds
Aromatic compounds exhibit unique reactivity patterns due to their stable resonance structures. The presence of substituents can significantly influence the reactivity; electron-donating groups enhance nucleophilicity, while electron-withdrawing groups can facilitate nucleophilic attacks. Understanding these effects is crucial for predicting the outcomes of reactions involving aromatic systems.
Video consigliato:
08:19Intro to Aromaticity
Pratica correlata
Domanda del libro di testo
Predict the product of the following substitution/addition reactions involving phenoxides.
(a)
853
views
Domanda del libro di testo
Assessment 24.22 asked why meta-dihydroxybenzene could not be oxidized to meta-quinone. The attempted oxidation instead gives rise to three different quinone products. Suggest a mechanism for the formation of each.
1126
views
Domanda del libro di testo
(a) Based on Figure 24.23, explain why meta-dihydroxybenzene is not oxidized to meta-quinone.
(b) If a meta-quinone is not produced, what would you expect the product of the oxidation of meta-dihydroxybenzene to be?
1017
views
Domanda del libro di testo
In light of Figure 24.22, provide a mechanism by which para-dihydroxybenzene is oxidized to para-quinone.
978
views
Domanda del libro di testo
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)
1010
views