Textbook Question
What is the product of each of the following reactions?
a.
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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 19a
What reactants are needed to synthesize each of the following compounds using a Heck reaction?
a. 
Verified step by step guidance1
Step 1: Identify the product structure. The compound shown contains a conjugated system with a double bond adjacent to a ketone group. This suggests that the Heck reaction was used to form the double bond between the alkene and the aromatic or vinyl halide precursor.
Step 2: Recall the Heck reaction mechanism. The Heck reaction involves the coupling of an alkene with an aryl or vinyl halide in the presence of a palladium catalyst and a base. The reaction forms a new C-C bond between the alkene and the halide.
Step 3: Analyze the structure to determine the alkene reactant. The product contains a double bond in the conjugated system, which likely originated from an alkene reactant. The alkene reactant should match the portion of the molecule containing the double bond.
Step 4: Determine the halide reactant. The portion of the molecule containing the ketone group likely originated from a vinyl halide reactant. A vinyl halide with the structure CH3-CH=CH-Br (or similar) would be appropriate.
Step 5: Combine the reactants. The alkene reactant (e.g., 2-methyl-1-butene) and the vinyl halide reactant (e.g., CH3-CH=CH-Br) can be coupled using the Heck reaction conditions: a palladium catalyst (e.g., Pd(OAc)2), a ligand (e.g., triphenylphosphine), and a base (e.g., triethylamine).
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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. Understanding the mechanism, which involves oxidative addition, transmetalation, and reductive elimination, is crucial for predicting the products and necessary reactants.
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Heck Reaction
Reactants in Heck Reaction
To successfully perform a Heck reaction, specific reactants are required: an aryl or vinyl halide, an alkene, a palladium catalyst, and a base. The halide provides the aryl or vinyl group, while the alkene serves as the coupling partner. The choice of base can influence the reaction's efficiency and selectivity, making it essential to select appropriate reactants based on the desired product structure.
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Product Structure Analysis
Analyzing the structure of the desired product is vital for determining the appropriate reactants for the Heck reaction. The product's functional groups, stereochemistry, and overall connectivity guide the selection of the starting materials. In this case, recognizing the presence of specific substituents and the overall carbon framework in the provided compound helps in identifying the necessary aryl or vinyl halide and alkene to achieve the synthesis.
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Related Practice
Textbook Question
What products are obtained from metathesis of each of the following alkenes?
b.
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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
Show how the Suzuki and/or Heck reactions can be used to prepare the following compounds:
a.
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Textbook Question
What is the product of each of the following reactions?
b.
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Textbook Question
What products are obtained from metathesis of each of the following alkenes?
a. CH3CH2CH=CH2
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