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 58a,b
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. 
Verified step by step guidance1
Step 1: Analyze the substituents on the benzene ring for each compound. Substituents influence the reactivity and regioselectivity of electrophilic aromatic substitution reactions, such as nitration. Electron-withdrawing groups (e.g., NO2, COOH) are deactivating and direct incoming groups to meta positions, while electron-donating groups (e.g., alkoxy groups) are activating and direct to ortho/para positions.
Step 2: For compound (a), the benzene ring has two substituents: a nitro group (-NO2) and a carboxylic acid group (-COOH). Both are electron-withdrawing and deactivating, directing incoming electrophiles to the meta positions relative to themselves. Identify the meta positions relative to each substituent and determine overlap.
Step 3: For compound (b), the benzene ring has two ester groups (-COOCH3). Ester groups are electron-withdrawing through resonance and inductive effects, but they are less deactivating compared to nitro groups. They direct incoming electrophiles to the meta positions relative to themselves. Identify the meta positions relative to each ester group and determine overlap.
Step 4: Consider steric hindrance in both compounds. In compound (a), the nitro and carboxylic acid groups may create steric hindrance at certain positions, potentially affecting the likelihood of nitration at those sites. Similarly, in compound (b), the ester groups may influence steric accessibility of the meta positions.
Step 5: Summarize the positions on the benzene ring for each compound that are most likely to undergo nitration based on the electronic and steric effects of the substituents. These positions are determined by the directing effects of the substituents and the overlap of meta positions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for understanding how substituents influence the reactivity of aromatic compounds. In the context of nitration, the electrophile is the nitronium ion (NO2+), generated from nitric acid and sulfuric acid, which attacks the electron-rich aromatic ring.
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EAS Review
Directing Effects of Substituents
Substituents on an aromatic ring can either be electron-donating or electron-withdrawing, affecting the position where new substituents are added during EAS. Electron-donating groups (like -OH or -OCH3) direct incoming electrophiles to the ortho and para positions, while electron-withdrawing groups (like -NO2 or -CF3) direct them to the meta position. Understanding these directing effects is essential for predicting the outcome of nitration reactions.
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Nitration Mechanism
The nitration mechanism involves the generation of the nitronium ion, which acts as the electrophile in the reaction. The mechanism proceeds through the formation of a sigma complex (arenium ion) after the electrophile attacks the aromatic ring, followed by deprotonation to restore aromaticity. Recognizing this mechanism helps in identifying which carbon atoms in the ring will be nitrated based on the existing substituents.
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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
Show two pairs of reagents that would each result in formation of the following compound:
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Textbook Question
What are the products of the following reactions?
f.
2
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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
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