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 16a
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 16aChapter 23, Problem 16a
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(a) 
Verified step by step guidance1
Identify the ether linkage in the given structure. The ether linkage is between the oxygen atom and the two carbon-containing groups.
Determine the two parts of the ether: the aryl group (phenyl group) and the alkyl group. In this structure, the aryl group is the phenyl ring, and the alkyl group is the isopropyl group attached to the oxygen.
To synthesize this ether, you need a phenoxide ion and an alkyl halide. The phenoxide ion is derived from phenol, where the hydrogen of the hydroxyl group is replaced by a metal ion, typically sodium or potassium.
The alkyl halide should correspond to the alkyl group in the ether. In this case, the alkyl group is isopropyl, so the alkyl halide should be isopropyl bromide or isopropyl chloride.
The reaction to form the ether is a nucleophilic substitution reaction, where the phenoxide ion acts as the nucleophile and attacks the electrophilic carbon in the alkyl halide, displacing the halide ion and forming the ether bond.
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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 synthesis.
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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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01:52How to name alkyl halides
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 is favored with primary halides to avoid elimination reactions. Understanding this mechanism is essential for selecting appropriate reactants to synthesize specific aryl alkyl ethers.
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03:50The Mechanism of Williamson Ether Synthesis.
Related Practice
Textbook Question
Predict the product of the following substitution/addition reactions involving phenoxides.
(a)
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Textbook Question
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
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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Textbook Question
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b)
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Textbook Question
Which proton, Ha or Hb, would you expect to have the lower pKa value?
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