Textbook Question
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(a)
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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 18a
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 18aChapter 23, Problem 18a
Predict the product of the following substitution/addition reactions involving phenoxides.
(a) 
Verified step by step guidance1
Identify the reactants: The first reactant is a chlorophenol, specifically 2-chlorophenol, and the second reactant is a chlorocyclopentane.
Recognize the role of NaOH: Sodium hydroxide (NaOH) is a strong base that can deprotonate the phenol group, forming a phenoxide ion.
Formation of phenoxide ion: The hydroxide ion (OH-) from NaOH will deprotonate the hydroxyl group (OH) of the phenol, resulting in the formation of a phenoxide ion (C6H4ClO-).
Nucleophilic substitution: The phenoxide ion, being a good nucleophile, will attack the electrophilic carbon in the chlorocyclopentane, displacing the chloride ion (Cl-) and forming an ether linkage.
Predict the product: The final product will be an ether, specifically a phenoxycyclopentane, where the phenoxide ion has replaced the chloride ion in the cyclopentane ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Phenoxide Ion Formation
Phenoxide ions are formed when phenol reacts with a strong base like NaOH. The hydroxyl group (OH) in phenol loses a hydrogen ion (H+), resulting in a negatively charged oxygen atom. This ion is more nucleophilic than phenol itself, making it more reactive in substitution reactions, particularly with alkyl halides.
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Nucleophilic Substitution Reaction
Nucleophilic substitution is a fundamental reaction where a nucleophile replaces a leaving group in a molecule. In this reaction, the phenoxide ion acts as the nucleophile, attacking the electrophilic carbon in the chlorinated compound, displacing the chloride ion. This process is crucial for forming new carbon-oxygen bonds in organic synthesis.
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Stereochemistry in Substitution Reactions
Stereochemistry plays a vital role in substitution reactions, especially when the substrate is a chiral molecule. The reaction can proceed via an SN1 or SN2 mechanism, affecting the stereochemical outcome. In this case, the reaction likely follows an SN2 mechanism, leading to an inversion of configuration at the chiral center where the chloride is replaced by the phenoxide group.
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Related Practice
Textbook Question
Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.
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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
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)
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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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