Textbook Question
What vinylic halide couples with styrene (C6H5-CH=CH2) in order to synthesize each of the following compounds using a Heck reaction?
c.
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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 37b
What are the products of the following reactions?
b. 
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a Suzuki coupling reaction, which is a palladium-catalyzed cross-coupling reaction between an aryl or vinyl halide and an organoboron compound.
Step 2: Identify the reactants. The first reactant is a brominated aromatic ketone (4-bromoacetophenone), and the second reactant is a cyclohexylboronic ester.
Step 3: Understand the role of the catalyst and base. Pd(PPh₃)₄ is the palladium catalyst, which facilitates the coupling reaction, and Na₂CO₃ acts as a base to activate the boronic ester.
Step 4: Predict the bond formation. The Suzuki reaction forms a new carbon-carbon bond between the carbon attached to the bromine atom in the aryl halide and the carbon attached to the boron atom in the boronic ester.
Step 5: Write the product structure. The product will be a substituted aromatic ketone where the bromine atom is replaced by the cyclohexyl group, resulting in 4-cyclohexylacetophenone.
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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 organoboron compound with an organic halide in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds and other complex organic molecules, making it essential for various applications in pharmaceuticals and materials science.
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04:02
Suzuki Reaction
Palladium Catalysis
Palladium catalysis is a key component in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the transfer of the organic group from the organoboron compound to the organic halide. The use of palladium allows for milder reaction conditions and higher selectivity, which is crucial for synthesizing complex organic structures efficiently.
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Base in Organic Reactions
In organic reactions, a base is often required to deprotonate the organoboron compound, generating a more reactive species that can participate in the coupling process. In the Suzuki reaction, sodium carbonate (Na2CO3) is commonly used as a base to facilitate the reaction. The choice of base can significantly influence the reaction's efficiency and the yield of the desired product.
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Related Practice
Textbook Question
What are the products of the following reactions?
d.
1144
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Textbook Question
Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
b.
660
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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
Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:
a.
1086
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Textbook Question
What are the products of the following reactions?
a.
b.
71
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