Textbook Question
What are the products of the following reactions?
d.
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Ch. 11 - Organometallic Compounds
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 12, Problem 34c
What vinylic halide couples with styrene (C6H5-CH=CH2) in order to synthesize each of the following compounds using a Heck reaction?
c. 
Verified step by step guidance1
Step 1: Recognize that the Heck reaction involves coupling a vinylic halide with an alkene, facilitated by a palladium catalyst (L2Pd) and a base such as triethylamine ((CH3CH2)3N). The product is formed by the substitution of the halide with the alkene, creating a new C-C bond.
Step 2: Analyze the target product structure. The product contains a styrene moiety (C6H5-CH=CH2) coupled to a vinylcyclopentane group. This indicates that the vinylic halide must contain the cyclopentane ring and the vinyl group.
Step 3: Identify the vinylic halide structure required. The halide must be attached to the vinyl group and the cyclopentane ring. This structure corresponds to vinylcyclopentane with a halogen atom (e.g., bromine or iodine) attached to the vinyl group.
Step 4: Write the chemical structure of the vinylic halide. The halide should be CH2=CH-X, where X is the halogen (e.g., Br or I), and it is bonded to the cyclopentane ring. This ensures compatibility with the Heck reaction mechanism.
Step 5: Confirm the reaction conditions. The palladium catalyst (L2Pd) and triethylamine base facilitate the coupling reaction, ensuring the formation of the desired product by replacing the halogen with the styrene moiety.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Heck Reaction
The Heck reaction is a palladium-catalyzed coupling reaction between an aryl or vinyl halide and an alkene, resulting in the formation of substituted alkenes. This reaction is significant in organic synthesis for constructing complex molecules and is widely used in the pharmaceutical and materials industries. The reaction typically requires a base and a palladium catalyst to facilitate the coupling process.
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Heck Reaction
Vinylic Halides
Vinylic halides are organic compounds where a halogen atom is bonded to a carbon atom that is part of a double bond (alkene). They are important intermediates in organic synthesis, particularly in reactions like the Heck reaction, where they can couple with alkenes to form more complex structures. Understanding the reactivity and properties of vinylic halides is crucial for predicting the outcomes of coupling reactions.
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Alkene Reactivity
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, making them more reactive than alkanes. Their reactivity is influenced by factors such as sterics and electronics, which affect how they participate in reactions like the Heck reaction. In this context, the ability of an alkene to undergo coupling with a vinylic halide is essential for synthesizing desired products, as seen in the provided reaction scheme.
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Related Practice
Textbook Question
Using ethynylcyclohexane as a starting material and any other needed reagents, how can the following compounds be synthesized?
a.
3606
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Textbook Question
What are the products of the following reactions?
b.
1034
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Textbook Question
What are the products of the following reactions?
a.
b.
71
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Textbook Question
What alkyl halide reacts with lithium divinylcuprate [(CH2=CH)2CuLi] for the synthesis of each of the following compounds?
a.
b.
877
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Textbook Question
What alkyl halide reacts with lithium divinylcuprate [(CH2=CH)2CuLi] for the synthesis of each of the following compounds?
c.
d.
1047
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