Textbook Question
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole
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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 52f
Show how the following compounds can be synthesized from benzene:
f. m-hydroxybenzoic acid
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. Perform a nitration reaction by treating benzene with a mixture of concentrated HNO₃ and H₂SO₄. This introduces a nitro group (-NO₂) onto the benzene ring, forming nitrobenzene.
Step 2: Reduce the nitro group (-NO₂) in nitrobenzene to an amino group (-NH₂) using a reducing agent such as Sn/HCl or Fe/HCl. This forms aniline.
Step 3: Protect the amino group (-NH₂) by acetylation. React aniline with acetic anhydride to form acetanilide. This step prevents unwanted reactions during subsequent steps.
Step 4: Perform a Friedel-Crafts acylation reaction on acetanilide using CO₂ and AlCl₃ to introduce a carboxylic acid group (-COOH) in the meta position relative to the protected amino group. This forms m-acetylaminobenzoic acid.
Step 5: Hydrolyze the acetanilide group under acidic or basic conditions to remove the acetyl group and regenerate the amino group. Then oxidize the amino group to a hydroxyl group (-OH) using a suitable oxidizing agent, such as NaNO₂/HCl, to yield m-hydroxybenzoic acid.
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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 synthesizing substituted aromatic compounds, such as m-hydroxybenzoic acid from benzene. Understanding the mechanism of EAS, including the role of the electrophile and the stability of the carbocation intermediate, is essential for predicting the products of reactions involving benzene derivatives.
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EAS Review
Ortho/Para vs. Meta Directing Groups
In electrophilic aromatic substitution, substituents on the benzene ring can influence the position of further substitutions. Ortho and para directing groups favor substitution at the 2 and 4 positions, while meta directing groups lead to substitution at the 3 position. Recognizing the directing effects of functional groups, such as hydroxyl (-OH) and carboxylic acid (-COOH), is vital for determining the correct synthesis pathway for m-hydroxybenzoic acid.
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04:42Ortho, Para major products
Functional Group Transformations
Functional group transformations involve converting one functional group into another through various chemical reactions. In the synthesis of m-hydroxybenzoic acid, the transformation of a nitrile (-CN) group into a carboxylic acid (-COOH) is a key step. Familiarity with common reactions, such as hydrolysis of nitriles, is necessary to understand how to achieve the desired functional groups in the final product.
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Related Practice
Textbook Question
Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene
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Textbook Question
For each horizontal row of substituted benzenes, indicate
c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.
1.
2.
921
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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
1236
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Textbook Question
For each horizontal row of substituted benzenes, indicate
c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.
3.
609
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Textbook Question
Show how the following compounds can be synthesized from benzene:
b. m-chloroethylbenzene
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