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 15b
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene
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, while electron-withdrawing groups (EWGs) decrease reactivity.
Step 2: Analyze the substituents on each compound. Dichloromethylbenzene (CCl3) and difluoromethylbenzene (CF3) are electron-withdrawing groups due to the electronegativity of chlorine and fluorine atoms. Toluene (CH3) and chloromethylbenzene (CH2Cl) are electron-donating groups, with CH3 being a stronger EDG than CH2Cl.
Step 3: Rank the substituents based on their electron-donating or electron-withdrawing effects. CH3 (toluene) is the strongest EDG, followed by CH2Cl (chloromethylbenzene). CCl3 (dichloromethylbenzene) and CF3 (difluoromethylbenzene) are EWGs, with CF3 being more strongly withdrawing than CCl3.
Step 4: Determine the reactivity of the compounds toward EAS. Compounds with EDGs will be more reactive, while those with EWGs will be less reactive. Therefore, the order of reactivity is: toluene > chloromethylbenzene > dichloromethylbenzene > difluoromethylbenzene.
Step 5: Summarize the reasoning. The reactivity order is based on the ability of the substituents to donate or withdraw electrons, which affects the electron density of the aromatic ring and its ability to react with electrophiles.
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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 donate or withdraw electron density, affecting the stability of the intermediate formed during the reaction.
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EAS Review
Electron-Withdrawing and Electron-Donating Groups
Substituents on an aromatic ring can be classified as electron-withdrawing groups (EWGs) or electron-donating groups (EDGs). EWGs, such as -CF3 and -Cl, decrease the electron density on the ring, making it less reactive towards electrophiles. In contrast, EDGs, like -CH3 (from toluene), increase electron density, enhancing reactivity in EAS reactions.
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Reactivity Order in EAS
The reactivity order of aromatic compounds in electrophilic aromatic substitution is determined by the electronic effects of substituents. Generally, compounds with EDGs are more reactive than those with EWGs. The presence of multiple substituents can complicate this order, as their combined effects must be considered to accurately predict the reactivity of each compound.
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Related Practice
Textbook Question
Draw the resonance contributors for:
a. benzaldehyde
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Textbook Question
For each horizontal row of substituted benzenes, indicateb. the one that is the least reactive in an electrophilic aromatic substitution reaction.
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Textbook Question
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, phenol, toluene, nitrobenzene, bromobenzene
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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