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 58c,d
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. 
Verified step by step guidance1
Step 1: Analyze the substituents on the benzene ring for compound c. The substituents are -OCH3 (methoxy group) and -Cl (chlorine). The methoxy group is an electron-donating group (activating, ortho/para-directing), while chlorine is an electron-withdrawing group (deactivating, ortho/para-directing). The methoxy group will dominate the directing effects due to its stronger activation.
Step 2: Predict the nitration sites for compound c. The methoxy group directs nitration to the ortho and para positions relative to itself. The chlorine group also directs nitration to its ortho and para positions, but its effect is weaker. Therefore, the nitration will primarily occur at the ortho and para positions relative to the methoxy group.
Step 3: Analyze the substituents on the benzene ring for compound d. The substituents are -OH (hydroxy group) and -COOH (carboxylic acid group). The hydroxy group is an electron-donating group (activating, ortho/para-directing), while the carboxylic acid group is an electron-withdrawing group (deactivating, meta-directing). The hydroxy group will dominate the directing effects due to its stronger activation.
Step 4: Predict the nitration sites for compound d. The hydroxy group directs nitration to the ortho and para positions relative to itself. The carboxylic acid group directs nitration to the meta position relative to itself, but its effect is weaker. Therefore, the nitration will primarily occur at the ortho and para positions relative to the hydroxy group.
Step 5: Summarize the nitration sites. For compound c, nitration occurs at the ortho and para positions relative to the methoxy group. For compound d, nitration occurs at the ortho and para positions relative to the hydroxy 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
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 compounds react with nitrating agents like HNO3 in the presence of H2SO4, which generates the nitronium ion (NO2+), the active electrophile in nitration.
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Aromaticity
Aromaticity refers to the special stability and reactivity of certain cyclic compounds that follow Huckel's rule, which states that a compound must have (4n + 2) π electrons to be considered aromatic. This property influences the positions on the ring that are susceptible to electrophilic attack, making it essential to identify which carbons can be nitrated.
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Regioselectivity in Nitration
Regioselectivity in nitration describes the preference of the electrophile to attack specific positions on the aromatic ring, influenced by substituents already present. Electron-donating groups activate the ring and direct substitution to ortho and para positions, while electron-withdrawing groups direct it to the meta position, which is critical for predicting the outcome of the nitration reaction.
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Related Practice
Textbook Question
Why is anisole nitrated more rapidly than thioanisole under the same conditions?
3
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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
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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