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 39b
b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.
chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene
Verified step by step guidance1
Identify the compounds provided in the problem and determine the substituents attached to the aromatic ring. Substituents can either activate or deactivate the ring toward electrophilic aromatic substitution (EAS). Activating groups increase the tendency for EAS, while deactivating groups decrease it.
Classify each substituent as either an electron-donating group (EDG) or an electron-withdrawing group (EWG). EDGs, such as -OH, -OCH3, and alkyl groups, stabilize the intermediate carbocation formed during EAS, making the reaction more favorable. EWGs, such as -NO2, -CF3, and -COOH, destabilize the intermediate carbocation, making the reaction less favorable.
Consider the resonance and inductive effects of each substituent. Resonance effects occur when the substituent can donate or withdraw electrons through π-bond interactions, while inductive effects involve electron withdrawal or donation through σ-bonds. Substituents with strong resonance-donating effects (e.g., -OH, -NH2) are typically stronger activators than those with only inductive effects.
Rank the compounds based on the overall activating or deactivating influence of their substituents. Compounds with strong activating groups will have the greatest tendency to undergo EAS, while those with strong deactivating groups will have the least tendency.
If multiple substituents are present on a single aromatic ring, evaluate their combined effects. Activating groups generally dominate over deactivating groups, but the position of the substituents (ortho, meta, or para) can also influence the reactivity. Use this information to finalize the ranking of the compounds.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction is crucial for modifying aromatic compounds and is influenced by the nature of substituents already present on the ring, which can either activate or deactivate the ring towards further substitution.
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EAS Review
Activating and Deactivating Groups
Substituents on an aromatic ring can be classified as activating or deactivating based on their electronic effects. Activating groups, such as -OH or -NH2, increase the electron density of the ring, making it more reactive towards electrophiles. In contrast, deactivating groups, like -NO2 or -CF3, withdraw electron density, reducing the ring's reactivity and influencing the position of substitution.
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Ortho/Para vs. Meta Directing
The position of substitution in electrophilic aromatic substitution is also determined by whether the substituents are ortho/para or meta directing. Activating groups typically direct incoming electrophiles to the ortho and para positions, while deactivating groups usually direct them to the meta position. Understanding these directing effects is essential for predicting the outcome of EAS reactions.
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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?
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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
Rank the following compounds from greatest tendency to least tendency to undergo nucleophilic aromatic substitution:
chlorobenzene
1-chloro-2,4-dinitrobenzene
p-chloronitrobenzene
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Textbook Question
Design a synthesis for each of the following, using an intramolecular reaction:
a.
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