Textbook Question
Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.
a. How can tyramine be prepared from b-phenylethylamine?
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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 101d
Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.
d. How can b-phenylethylamine be prepared from benzyl chloride?
Verified step by step guidance1
Step 1: Begin with benzyl chloride (C6H5CH2Cl), which contains a benzene ring attached to a CH2Cl group. The goal is to convert the CH2Cl group into a CH2CH2NH2 group to form β-phenylethylamine.
Step 2: Perform a nucleophilic substitution reaction to replace the chlorine atom with a cyanide group (-CN). This can be achieved using potassium cyanide (KCN) in an appropriate solvent like ethanol. The reaction produces benzyl cyanide (C6H5CH2CN).
Step 3: Reduce the nitrile group (-CN) in benzyl cyanide to an amine group (-CH2NH2). This reduction can be carried out using hydrogen gas (H2) and a metal catalyst such as palladium on carbon (Pd/C) or lithium aluminum hydride (LiAlH4). The product is β-phenylethylamine (C6H5CH2CH2NH2).
Step 4: Purify the β-phenylethylamine product using techniques such as distillation or recrystallization, depending on the physical properties of the compound.
Step 5: Verify the structure and purity of the β-phenylethylamine using spectroscopic methods such as NMR (nuclear magnetic resonance) or IR (infrared spectroscopy).
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkaloids
Alkaloids are a class of naturally occurring organic compounds that mostly contain basic nitrogen atoms. They are often derived from plant sources and have significant pharmacological effects on humans and animals. Tyramine, found in foods like ripe cheese, is an example of an alkaloid that can influence neurotransmitter activity in the brain.
Neurotransmitters
Neurotransmitters are chemical messengers that transmit signals across synapses from one neuron to another in the nervous system. Dopamine is a well-known neurotransmitter that plays a crucial role in mood regulation, reward, and motor control. Understanding the structure and function of neurotransmitters is essential for grasping their impact on behavior and physiology.
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09:04
Benzene Nomenclature
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of preparing β-phenylethylamine from benzyl chloride, the nucleophile (an amine) attacks the carbon atom bonded to the chlorine, resulting in the formation of the desired amine product. This reaction is key for synthesizing various organic compounds.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.