Textbook Question
Predict the product(s) of the following nucleophilic aromatic substitution reactions occurring by the benzyne mechanism.
(b)
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Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions
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. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 53c
Mullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 53cChapter 22, Problem 53c
Predict the products of the following nucleophilic aromatic substitution reactions.
(c) 
Verified step by step guidance1
Identify the type of reaction: This is a nucleophilic aromatic substitution (NAS) reaction, which typically involves the replacement of a leaving group (such as Cl) on an aromatic ring by a nucleophile.
Recognize the role of the strong base: Sodium hydride (NaH) is a strong base that will deprotonate the alcohol group, forming an alkoxide ion. This alkoxide ion will act as the nucleophile in the reaction.
Determine the position of substitution: In NAS reactions, the nucleophile will attack the carbon atom that is ortho or para to an electron-withdrawing group, such as the ester group in this molecule. The chlorine atom is ortho to the ester group, making it a suitable leaving group.
Consider the mechanism: The alkoxide ion will attack the aromatic ring at the position of the chlorine atom, leading to the displacement of the chlorine and formation of a new C-O bond.
Predict the product: The final product will be an aromatic compound where the chlorine atom has been replaced by the alkoxide group, resulting in an ether linkage between the aromatic ring and the alkoxide group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Aromatic Substitution
Nucleophilic aromatic substitution involves the replacement of a leaving group, such as a halide, on an aromatic ring by a nucleophile. This reaction typically requires strong electron-withdrawing groups on the ring to stabilize the intermediate. The reaction proceeds through either an addition-elimination mechanism or a benzyne mechanism, depending on the conditions and substrates involved.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Role of Strong Bases
Strong bases, like sodium hydride (NaH), are used to deprotonate nucleophiles, enhancing their nucleophilicity. In nucleophilic aromatic substitution, a strong base can generate a negatively charged nucleophile, which is more reactive towards the electrophilic aromatic ring. This increased reactivity is crucial for facilitating the substitution process, especially when the aromatic ring is not highly activated.
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Leaving Group Ability
The leaving group ability is a critical factor in nucleophilic aromatic substitution reactions. Chlorine, as a halide, is a common leaving group due to its ability to stabilize the negative charge upon departure. The effectiveness of a leaving group is influenced by its electronegativity and the stability of the resulting anion, which impacts the overall rate and feasibility of the substitution reaction.
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Related Practice
Textbook Question
Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.
(d)
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Textbook Question
Predict the major product of the following electrophilic aromatic substitution reactions.
(c)
600
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Textbook Question
Predict the products of the following reactions.
(a)
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Textbook Question
Assume that Ha is the proton removed in the first step of the benzyne mechanism with p-chlorotoluene. Draw the benzyne intermediate and identify the two products that will result.
360
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Textbook Question
Predict the products of the following electrophilic aromatic substitution reactions.
(b)
545
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