Textbook Question
What are the products of the following reactions?
c.
d.
1
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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 57f
What are the products of the following reactions?
f. 
Verified step by step guidance1
Step 1: Recognize the type of reaction. This is an electrophilic aromatic substitution reaction where bromine (Br2) reacts with the aromatic ring in the presence of a Lewis acid catalyst (FeBr3). The Lewis acid FeBr3 helps generate the electrophile Br+.
Step 2: Analyze the structure of the aromatic compound. The benzene ring is substituted with a trichloromethyl group (-CCl3), which is an electron-withdrawing group. Electron-withdrawing groups deactivate the ring and direct substitution to the meta position.
Step 3: Generate the electrophile. FeBr3 reacts with Br2 to form the bromonium ion (Br+), which acts as the electrophile in this reaction. The reaction can be represented as:
Step 4: Determine the site of substitution. The trichloromethyl group (-CCl3) directs the bromine to the meta position due to its electron-withdrawing nature. The bromonium ion (Br+) will attack the meta position relative to the -CCl3 group.
Step 5: Complete the reaction mechanism. After the bromonium ion (Br+) substitutes at the meta position, the aromaticity of the benzene ring is restored by the loss of a proton (H+). The final product is a brominated benzene ring with the bromine at the meta position relative to the -CCl3 group.
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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 process typically involves the formation of a sigma complex, where the aromaticity is temporarily lost, followed by deprotonation to restore aromaticity. Understanding EAS is crucial for predicting the products of reactions involving aromatic compounds.
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EAS Review
Role of Lewis Acids
Lewis acids, such as FeBr3 in this reaction, are substances that can accept an electron pair from a Lewis base. In the context of EAS, FeBr3 acts as a catalyst by forming a more reactive electrophile from Br2, facilitating the substitution reaction. Recognizing the role of Lewis acids is essential for understanding how certain reactions proceed and the stability of intermediates formed.
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Regioselectivity in Substitution Reactions
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In EAS reactions, the presence of substituents on the aromatic ring can influence the position where the electrophile attacks, leading to ortho, meta, or para products. Analyzing the substituents' electronic effects is vital for predicting the major products of the reaction.
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Related Practice
Textbook Question
For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO3/H2SO4:
c.
d.
2
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Textbook Question
For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO3/H2SO4:
e.
f.
1
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Textbook Question
For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO3/H2SO4:
a.
b.
7
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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
1
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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
3
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