Textbook Question
What is the product of each of the following reactions?
a.
5
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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 14c
What aryl or vinylic halides would you use to synthesize the following compounds, using the alkenylorganoboron compound shown here?
c. 
Verified step by step guidance1
Step 1: Analyze the alkenylorganoboron compound provided in the image. The compound contains a boronic ester group attached to an alkenyl group, which can participate in Suzuki coupling reactions. Suzuki coupling is a palladium-catalyzed cross-coupling reaction between an organoboron compound and an aryl or vinylic halide.
Step 2: Examine the target compound shown in the image. The target molecule contains a conjugated system with an aryl group and an extended alkenyl chain. This suggests that the reaction involves coupling the alkenylorganoboron compound with an appropriate halide to form the desired structure.
Step 3: Identify the halide required for the coupling reaction. The target molecule has a phenyl group attached to the alkenyl chain. To achieve this, an aryl halide, such as bromobenzene or iodobenzene, can be used as the coupling partner.
Step 4: Consider the reaction conditions. The Suzuki coupling typically requires a palladium catalyst (e.g., Pd(PPh3)4), a base (e.g., K2CO3 or NaOH), and a solvent such as tetrahydrofuran (THF) or water. These conditions facilitate the formation of the C-C bond between the alkenylorganoboron compound and the aryl halide.
Step 5: Summarize the synthesis. To synthesize the target compound, use the alkenylorganoboron compound provided in the image and an aryl halide, such as bromobenzene or iodobenzene, under Suzuki coupling conditions. This will result in the formation of the desired conjugated system with the phenyl group attached to the alkenyl chain.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Suzuki Coupling Reaction
The Suzuki coupling reaction is a widely used method in organic chemistry for forming carbon-carbon bonds. It involves the reaction of an aryl or vinylic halide with an alkenylorganoboron compound in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing complex organic molecules, allowing for the introduction of various functional groups.
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Suzuki Reaction
Aryl and Vinylic Halides
Aryl halides are compounds where a halogen atom is bonded to an aromatic ring, while vinylic halides have a halogen atom attached to a carbon-carbon double bond. Both types of halides are important in organic synthesis, especially in reactions like the Suzuki coupling, where they serve as electrophiles that react with nucleophilic organoboron compounds to form new carbon-carbon bonds.
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Alkenylorganoboron Compounds
Alkenylorganoboron compounds are organoboron species that contain a carbon-carbon double bond. They act as nucleophiles in the Suzuki reaction, reacting with aryl or vinylic halides to form new alkenes. The versatility of these compounds allows for the synthesis of a wide range of products, making them essential in the development of pharmaceuticals and advanced materials.
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Related Practice
Textbook Question
What is the product of each of the following reactions?
a.
1
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Textbook Question
What is the product of each of the following reactions?
b.
1
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Textbook Question
The Stille reaction is similar to the Suzuki reaction. It replaces the alkenyl-organoboron compound of the Suzuki reaction with an alkenyl-organotin compound. (R is an alkyl group such as methyl or butyl.) Unlike the alkenyl-organoboron compound that always has a trans configuration, the alkenyl-organotin compound can have a cis configuration. What is the product of the Stille reaction shown here?
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Textbook Question
How could the following compounds be prepared, using cyclohexene as a starting material?
d.
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Textbook Question
What hydrocarbon would you use to prepare the organoboron compound in Problem 14?
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