Textbook Question
What are the products of the following reactions?
c.
d.
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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 55b
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene
Verified step by step guidance1
Step 1: Understand the concept of electrophilic aromatic substitution (EAS). EAS is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. The reactivity of the aromatic compound depends on the substituents already present on the ring, which can either activate or deactivate the ring toward electrophilic attack.
Step 2: Analyze the substituents on each compound. Substituents can be electron-donating groups (EDGs) or electron-withdrawing groups (EWGs). EDGs increase the electron density on the aromatic ring, making it more reactive toward electrophiles, while EWGs decrease the electron density, making the ring less reactive.
Step 3: For 1-chloro-2,4-dinitrobenzene, the substituents are a chlorine atom (weakly electron-withdrawing due to its inductive effect but slightly donating via resonance) and two nitro groups (strongly electron-withdrawing due to their -NO₂ groups). The nitro groups significantly deactivate the ring toward EAS.
Step 4: For 2,4-dinitrophenol, the substituents are a hydroxyl group (-OH, a strong electron-donating group via resonance) and two nitro groups (strongly electron-withdrawing). The hydroxyl group partially counteracts the deactivating effect of the nitro groups, making this compound more reactive than 1-chloro-2,4-dinitrobenzene.
Step 5: For 1-methyl-2,4-dinitrobenzene, the substituents are a methyl group (-CH₃, a weak electron-donating group via hyperconjugation) and two nitro groups (strongly electron-withdrawing). The methyl group slightly increases the reactivity of the ring compared to 1-chloro-2,4-dinitrobenzene but less so than the hydroxyl group in 2,4-dinitrophenol. Rank the compounds based on these observations.
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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. The reactivity of the aromatic compound 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 -Cl, withdraw electron density, reducing reactivity.
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Ortho/Para vs. Meta Directing
The position of substituents on an aromatic ring affects the orientation of new substituents during EAS. Activating groups typically direct new electrophiles to the ortho and para positions, while deactivating groups often direct them to the meta position. Understanding these directing effects is crucial for predicting the reactivity and product distribution in EAS reactions.
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Related Practice
Textbook Question
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole
625
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Textbook Question
Show how the following compounds can be synthesized from benzene:
f. m-hydroxybenzoic acid
1962
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Textbook Question
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene
1236
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Textbook Question
Show how the following compounds can be synthesized from benzene:
b. m-chloroethylbenzene
1801
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Textbook Question
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene
1388
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