Textbook Question
Acetaminophen is the active ingredient in Tylenol. How can acetominophen be synthesized from benzene?
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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 101e
Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.
e. How can b-phenylethylamine be prepared from benzaldehyde?
Verified step by step guidance1
Step 1: Begin with benzaldehyde (C6H5CHO) as the starting material. Benzaldehyde contains a benzene ring with an aldehyde functional group (-CHO). The goal is to convert this aldehyde into β-phenylethylamine, which has an amine group (-NH2) attached to a two-carbon chain connected to the benzene ring.
Step 2: Perform a reductive amination reaction. First, convert benzaldehyde into phenylacetaldehyde (C6H5CH2CHO) by using a reagent such as ethylmagnesium bromide (Grignard reagent) followed by hydrolysis. This step introduces a methylene (-CH2-) group between the benzene ring and the aldehyde group.
Step 3: React phenylacetaldehyde with ammonia (NH3) or a primary amine in the presence of a reducing agent such as sodium cyanoborohydride (NaBH3CN) or hydrogen gas with a metal catalyst (e.g., Pd/C). This step replaces the aldehyde group (-CHO) with an amine group (-NH2), forming β-phenylethylamine.
Step 4: Purify the product using techniques such as recrystallization or distillation to isolate β-phenylethylamine. Ensure the reaction conditions are optimized to minimize side reactions and maximize yield.
Step 5: Confirm the structure of β-phenylethylamine using spectroscopic methods such as NMR (nuclear magnetic resonance) or IR (infrared spectroscopy) to verify the presence of the amine group and the two-carbon chain attached to the benzene ring.
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aromatic Compounds
Aromatic compounds are cyclic structures that follow Huckel's rule, containing alternating double bonds and a planar configuration. They exhibit unique stability due to resonance, which allows for delocalization of electrons. Understanding aromaticity is crucial for predicting the reactivity and properties of compounds like tyramine and dopamine, which are both aromatic amines.
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Amines and Their Reactions
Amines are organic compounds derived from ammonia by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles in various reactions, including alkylation and acylation. The preparation of b-phenylethylamine from benzaldehyde involves the reduction of an intermediate, highlighting the importance of understanding amine chemistry in organic synthesis.
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Synthetic Pathways in Organic Chemistry
Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. In the context of preparing b-phenylethylamine from benzaldehyde, one must consider the necessary reagents and reaction conditions, such as reduction methods. Familiarity with these pathways is essential for effective problem-solving in organic synthesis.
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