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 17
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 17Chapter 23, Problem 17
Predict the product when the dihydroxybenzene shown is treated with a single equivalent of both base and haloalkane.
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Identify the functional groups in the dihydroxybenzene. The compound has two hydroxyl (OH) groups and a nitro (NO2) group attached to a benzene ring.
Recognize that the reaction involves a base (NaOH) and a haloalkane. The base will deprotonate one of the hydroxyl groups, forming a phenoxide ion.
Determine which hydroxyl group is more acidic. The presence of the electron-withdrawing nitro group increases the acidity of the hydroxyl group ortho to it, making it more likely to be deprotonated.
Consider the nucleophilic substitution reaction. The phenoxide ion, being a strong nucleophile, will attack the haloalkane, displacing the bromide ion and forming an ether linkage.
Predict the product structure. The reaction will result in the formation of an ether, where the alkyl group from the haloalkane is attached to the oxygen of the deprotonated hydroxyl group on the benzene ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dihydroxybenzene Reactivity
Dihydroxybenzenes, also known as catechols or resorcinols, contain two hydroxyl (-OH) groups on a benzene ring. The position of these groups affects the reactivity of the compound, particularly in nucleophilic substitution reactions. Understanding how these substituents influence electron density and steric hindrance is crucial for predicting the outcome of reactions with haloalkanes.
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01:17
Reactivity of Molecules
Nucleophilic Substitution Mechanism
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of haloalkanes, the reaction can proceed via either an SN1 or SN2 pathway, depending on the structure of the haloalkane and the conditions. Recognizing which mechanism is favored helps in predicting the product formed when a dihydroxybenzene reacts with a haloalkane.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Base-Driven Deprotonation
When a dihydroxybenzene is treated with a base, one of the hydroxyl groups can be deprotonated, generating a phenoxide ion. This ion is a stronger nucleophile than the neutral dihydroxybenzene, enhancing its reactivity towards electrophiles like haloalkanes. Understanding the role of the base in facilitating this deprotonation is essential for predicting the product of the reaction.
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1:23Nitrogenous Bases Example 3
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
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)
2
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