Textbook Question
What product(s) result from nitration of each of the following?
e. benzenesulfonic acid
f. cyclohexylbenzene
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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 15a
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, phenol, toluene, nitrobenzene, bromobenzene
Verified step by step guidance1
Step 1: Understand the concept of electrophilic aromatic substitution (EAS). EAS involves the attack of an electrophile on an aromatic ring, and the reactivity depends on the substituents attached to the ring. Electron-donating groups (EDGs) increase reactivity by activating the ring, while electron-withdrawing groups (EWGs) decrease reactivity by deactivating the ring.
Step 2: Analyze the substituents on each compound. Benzene (I) has no substituents, phenol (II) has an -OH group (strong EDG), toluene (III) has a -CH3 group (weak EDG), nitrobenzene (IV) has a -NO2 group (strong EWG), and bromobenzene (V) has a -Br group (weak EWG).
Step 3: Rank the substituents based on their activating or deactivating effects. The -OH group in phenol is the strongest activator, followed by the -CH3 group in toluene. Benzene is neutral, while -Br in bromobenzene is a weak deactivator, and -NO2 in nitrobenzene is the strongest deactivator.
Step 4: Arrange the compounds from most reactive to least reactive toward EAS based on the substituents' effects. Phenol (II) will be the most reactive due to the strong activation by the -OH group, followed by toluene (III), benzene (I), bromobenzene (V), and finally nitrobenzene (IV) as the least reactive due to the strong deactivation by the -NO2 group.
Step 5: Verify the reasoning by considering resonance and inductive effects. The -OH group in phenol donates electrons through resonance, greatly activating the ring. The -CH3 group in toluene donates electrons via hyperconjugation, moderately activating the ring. Benzene has no substituents, so it is neutral. The -Br group in bromobenzene withdraws electrons weakly via inductive effects, slightly deactivating the ring. The -NO2 group in nitrobenzene strongly withdraws electrons via resonance and inductive effects, making it the least reactive.
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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 electrophilic attack.
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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 (from phenol) and -CH3 (from toluene), increase the electron density of the ring, making it more reactive towards electrophiles. In contrast, deactivating groups, like -NO2 (from nitrobenzene), withdraw electron density, reducing reactivity.
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03:27Activating and deactivating groups
Resonance and Stability
Resonance refers to the delocalization of electrons across the aromatic system, which stabilizes the molecule. The stability of the intermediate formed during EAS is crucial; more stable intermediates lead to faster reactions. For example, phenol is more reactive than benzene due to the resonance stabilization provided by the -OH group, which enhances the electron density on the ring.
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03:43The radical stability trend.
Related Practice
Textbook Question
Correct the following incorrect names:
c. para-methylbromobenzene
d. 1,6-dichlorobenzene
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Textbook Question
Draw the resonance contributors for:
a. benzaldehyde
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Textbook Question
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene
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Textbook Question
Explain why fluorobenzene is more reactive than chlorobenzene toward electrophilic aromatic substitution but chloromethylbenzene is more reactive than fluoromethylbenzene.
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Textbook Question
Correct the following incorrect names:
e. meta-bromotoluene
f. 6-ethyl-4-iodoaniline
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