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 43b
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.
Verified step by step guidance1
Step 1: Analyze the target molecule, methamphetamine. It consists of a phenyl group (benzene ring) attached to a CH2 group, which is further connected to a CH group bearing a methyl group and an amine group (NHCH3). The synthesis will involve constructing this structure step by step.
Step 2: Start with benzyl chloride (C6H5CH2Cl), which contains a phenyl group and a CH2 group. Benzyl chloride can be synthesized from benzene (C6H6) via a Friedel-Crafts alkylation reaction using chloromethane (CH3Cl) and AlCl3 as a catalyst.
Step 3: Perform a nucleophilic substitution reaction on benzyl chloride to replace the chlorine atom with a cyanide group (CN). This can be achieved using sodium cyanide (NaCN) in an appropriate solvent. The product will be benzyl cyanide (C6H5CH2CN).
Step 4: Reduce the nitrile group (-CN) in benzyl cyanide to a primary amine (-CH2NH2) using a reducing agent such as lithium aluminum hydride (LiAlH4). This will yield phenyl-ethylamine (C6H5CH2CH2NH2).
Step 5: Methylate the amine group in phenyl-ethylamine to form methamphetamine. This can be done using formaldehyde (HCHO) and hydrogen gas (H2) in the presence of a catalyst such as palladium on carbon (Pd/C). The methyl group will be added to the nitrogen atom, completing the synthesis of methamphetamine.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organic Synthesis
Organic synthesis is the process of constructing complex organic molecules from simpler ones through a series of chemical reactions. Understanding the principles of organic synthesis is crucial for devising pathways to create specific compounds, such as methamphetamine, while considering the functional groups and reaction mechanisms involved.
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Synthesis of Amino Acids: Strecker Synthesis Example 1
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying and manipulating functional groups is essential in organic synthesis, as they dictate the reactivity and properties of the compounds being synthesized, including the target drug.
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Reaction Mechanisms
Reaction mechanisms describe the step-by-step sequence of elementary reactions by which overall chemical change occurs. A solid grasp of reaction mechanisms is vital for predicting the outcomes of synthetic routes and for understanding how to effectively transform starting materials into the desired product, such as methamphetamine.
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Related Practice
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 Novocaine from benzene and any other reagents of four carbons or fewer.
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(g)
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Textbook Question
Using any necessary reagents, show how you would accomplish the following syntheses.
(e)
(f)
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