Textbook Question
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(a) 3-ethylbenzoic acid
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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 44
Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. Perform a nitration reaction using concentrated HNO₃ and H₂SO₄ to introduce a nitro group (-NO₂) onto the benzene ring, forming nitrobenzene.
Step 2: Reduce the nitro group in nitrobenzene to an amino group (-NH₂) using a reducing agent such as Sn/HCl or catalytic hydrogenation (H₂/Pd). This will yield aniline.
Step 3: Protect the amino group in aniline by acetylation. React aniline with acetic anhydride (CH₃CO₂O) to form acetanilide, which prevents unwanted side reactions during subsequent steps.
Step 4: Perform a Friedel-Crafts acylation on acetanilide using chloroacetyl chloride (ClCH₂COCl) and AlCl₃ as a catalyst. This introduces a chloroacetyl group onto the benzene ring.
Step 5: React the chloroacetyl derivative with diethylamine (CH₃CH₂NHCH₂CH₃) to replace the chlorine atom with a diethylamino group, forming Novocaine. Finally, hydrolyze the acetanilide group back to the amino group (-NH₂) using acidic or basic conditions.
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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, such as benzene. This reaction is crucial for synthesizing complex molecules from simpler aromatic compounds. In the context of synthesizing Novocaine, EAS can be used to introduce functional groups onto the benzene ring, which is essential for further transformations.
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Amine Functional Group
The amine functional group, characterized by the presence of a nitrogen atom bonded to one or more alkyl or aryl groups, plays a significant role in organic synthesis. Amines can act as nucleophiles, participating in various reactions, including the formation of amides and the introduction of nitrogen into organic molecules. In the synthesis of Novocaine, the amine group is critical for its anesthetic properties and overall structure.
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Carbon Chain Length and Reactivity
Understanding the reactivity of carbon chains with four carbons or fewer is essential in organic synthesis. Short carbon chains can serve as building blocks for more complex molecules, influencing the reaction pathways and products formed. In the synthesis of Novocaine, selecting appropriate reagents with the correct carbon chain length is vital to ensure successful reactions and the desired final product.
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Related Practice
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.
(b) Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue.
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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.
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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.
(a) Phenacetin, used with aspirin and caffeine in pain-relief medications.
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Textbook Question
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(c) 2-methyl-5-hydroxybenzoic acid
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