Textbook Question
Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.
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Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- 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 I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: 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 I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: 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: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 18d
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 18dChapter 23, Problem 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) 
Verified step by step guidance1
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.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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.
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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.
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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.
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Related Practice
Textbook Question
Predict the product of the following substitution/addition reactions involving phenoxides.
(a)
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Textbook Question
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.
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Textbook Question
(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?
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Textbook Question
In light of Figure 24.22, provide a mechanism by which para-dihydroxybenzene is oxidized to para-quinone.
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Textbook Question
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)
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