Textbook Question
Propose mechanisms for the following reactions.
(a)
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 19, Problem 45c
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(c) 2-methyl-5-hydroxybenzoic acid
Verified step by step guidance1
Start with benzene as the base compound. Perform a nitration reaction by treating benzene with a mixture of concentrated HNO₃ and H₂SO₄. This introduces a nitro group (-NO₂) to the benzene ring, forming nitrobenzene.
Reduce the nitro group (-NO₂) in nitrobenzene to an amino group (-NH₂) by using a reducing agent such as Sn/HCl or Fe/HCl. This forms aniline (C₆H₅NH₂).
Convert the amino group (-NH₂) in aniline to a diazonium ion (-N₂⁺) by treating it with NaNO₂ and HCl at 0–5°C. This forms benzene diazonium chloride (C₆H₅N₂⁺Cl⁻).
Perform a Sandmeyer reaction to introduce a carboxylic acid group (-COOH) at the para position relative to the diazonium group. Use CuCN followed by hydrolysis to achieve this transformation, forming para-aminobenzoic acid.
Introduce the methyl group (-CH₃) and hydroxyl group (-OH) at the appropriate positions. Use Friedel-Crafts alkylation with CH₃Cl/AlCl₃ to add the methyl group, and then perform selective hydroxylation using appropriate reagents to obtain 2-methyl-5-hydroxybenzoic acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Benzene and its Derivatives
Benzene is a fundamental aromatic hydrocarbon characterized by its stable ring structure and delocalized π-electrons. Understanding benzene's reactivity is crucial, as it undergoes electrophilic substitution reactions rather than addition, allowing for the introduction of various functional groups while preserving the aromatic system.
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02:49
Aromatic synthesis starting with benzene/benzene derivatives
Diazonium Ions
Diazonium ions are highly reactive intermediates formed from aromatic amines and nitrous acid. They play a pivotal role in organic synthesis, particularly in electrophilic aromatic substitution reactions, where they can be used to introduce various substituents onto the benzene ring, such as hydroxyl or carboxylic acid groups.
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Functional Group Transformation
Functional group transformation involves converting one functional group into another through chemical reactions. In the context of synthesizing 2-methyl-5-hydroxybenzoic acid, understanding how to manipulate functional groups, such as converting diazonium ions into hydroxyl or carboxylic acid groups, is essential for achieving the desired product.
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Related Practice
Textbook Question
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(a) 3-ethylbenzoic acid
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Textbook Question
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(d) 4-methoxyaniline
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Textbook Question
The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.
(c) Dopamine, one of the neurotransmitters in the brain. Parkinson’s disease is thought to result from a dopamine deficiency.
2
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Textbook Question
Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.
3
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Textbook Question
Propose mechanisms for the following reactions.
(b)
1
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