Textbook Question
Show how each of the following compounds can be synthesized from benzene:
c. p-bromoanisole
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 19, Problem 39a
Rank the following compounds from greatest tendency to least tendency to undergo nucleophilic aromatic substitution:
chlorobenzene
1-chloro-2,4-dinitrobenzene
p-chloronitrobenzene
Verified step by step guidance1
Identify the key factors that influence the tendency of a compound to undergo nucleophilic aromatic substitution (NAS). These include the presence of electron-withdrawing groups (EWGs) on the aromatic ring, their positions relative to the leaving group (chlorine in this case), and the stability of the intermediate Meisenheimer complex formed during the reaction.
Analyze chlorobenzene. Chlorobenzene lacks any electron-withdrawing groups on the aromatic ring. This means it has a very low tendency to undergo nucleophilic aromatic substitution because the intermediate Meisenheimer complex would not be stabilized.
Examine 1-chloro-2,4-dinitrobenzene. This compound has two strong electron-withdrawing nitro groups (-NO₂) at the ortho and para positions relative to the chlorine atom. These groups strongly stabilize the negative charge on the intermediate Meisenheimer complex, making this compound highly reactive in nucleophilic aromatic substitution.
Evaluate p-chloronitrobenzene. This compound has one nitro group (-NO₂) at the para position relative to the chlorine atom. While it is less reactive than 1-chloro-2,4-dinitrobenzene due to having only one EWG, the nitro group still stabilizes the intermediate Meisenheimer complex, making it more reactive than chlorobenzene.
Rank the compounds based on their tendency to undergo nucleophilic aromatic substitution: 1-chloro-2,4-dinitrobenzene (greatest tendency) > p-chloronitrobenzene > chlorobenzene (least tendency).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Aromatic Substitution (NAS)
Nucleophilic aromatic substitution is a reaction where a nucleophile replaces a leaving group on an aromatic ring. This process is facilitated by the presence of electron-withdrawing groups, which stabilize the negative charge on the intermediate Meisenheimer complex. Understanding the mechanism and conditions that favor NAS is crucial for predicting the reactivity of aromatic compounds.
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NAS in the addition-elimination pathway
Electron-Withdrawing Groups (EWGs)
Electron-withdrawing groups are substituents that pull electron density away from the aromatic ring, enhancing its susceptibility to nucleophilic attack. Common EWGs include nitro (-NO2) and cyano (-CN) groups. The presence and position of these groups significantly influence the reactivity of the aromatic compound in nucleophilic aromatic substitution reactions.
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02:37Donating vs Withdrawing Groups
Resonance and Stability
Resonance refers to the delocalization of electrons within a molecule, which can stabilize charged intermediates. In the context of nucleophilic aromatic substitution, compounds with strong resonance stabilization of the negative charge in the intermediate are more likely to undergo substitution. The stability of the intermediate formed during the reaction is a key factor in determining the tendency of the compound to react.
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03:43The radical stability trend.
Related Practice
Textbook Question
Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene were to react with hydroxide ion. Why doesn't the reaction occur?
1006
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Textbook Question
Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.
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Textbook Question
Show how each of the following compounds can be synthesized from benzene:
d. anisole
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Textbook Question
b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.
chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene
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Textbook Question
Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?
802
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