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 16b
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 16bChapter 23, Problem 16b
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b) 
Verified step by step guidance1
Identify the ether linkage in the given structure. The structure is a 1,4-dioxane derivative with two ether linkages.
Recognize that the ether can be synthesized by the Williamson ether synthesis, which involves the reaction of a phenoxide ion with an alkyl halide.
Determine the phenoxide ion needed. In this case, the phenoxide ion would be derived from the aromatic ring with an oxygen atom attached, specifically a catechol derivative.
Identify the alkyl halide required. The alkyl halide should correspond to the alkyl chain that forms the ether linkage. Here, a 1,2-dibromoethane can be used to form the two ether linkages.
Propose the reaction: React catechol with 1,2-dibromoethane under basic conditions to form the desired aryl alkyl ether through a double Williamson ether synthesis.
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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 a phenol loses a hydrogen ion (H+) from its hydroxyl group (-OH), resulting in a negatively charged oxygen atom. This ion is a strong nucleophile, making it highly reactive in nucleophilic substitution reactions. Understanding the stability and reactivity of phenoxide ions is crucial for predicting their behavior in ether formation.
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Metal Ion Catalysis Concept 1
Alkyl Halide
An alkyl halide is a compound derived from an alkane by replacing one or more hydrogen atoms with halogen atoms (such as chlorine, bromine, or iodine). These compounds are important in organic synthesis as they can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile, such as a phenoxide ion, to form ethers.
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Williamson Ether Synthesis
Williamson ether synthesis is a method for producing ethers by reacting an alkoxide ion (derived from an alcohol) with a primary alkyl halide. This reaction typically proceeds via an SN2 mechanism, where the nucleophile attacks the electrophilic carbon of the alkyl halide, leading to the formation of an ether. Understanding this mechanism is essential for designing the synthesis of specific aryl alkyl ethers.
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03:50The Mechanism of Williamson Ether Synthesis.
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
Predict the product of the following substitution/addition reactions involving phenoxides.
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Fluoxetine hydrochloride (Prozac®) is a widely used antidepressant. How might you stereoselectively install the indicated ether functional group (ROR) in (R)-fluoxetine?
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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
Though the nitro group is electron-withdrawing by resonance, when in the meta position, it doesn’t communicate by resonance with the phenoxide anion. And yet, the pKₐ value of m-nitrophenol is lowered from 10 (the pKₐ value of unsubstituted phenol) to 8.4. Explain this observation.
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