Textbook Question
What aryl or vinylic halides would you use to synthesize the following compounds, using the alkenylorganoboron compound shown here?
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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 17a
What is the product of each of the following reactions?
a. 
Verified step by step guidance1
Step 1: Identify the reaction type. This is a typical example of a palladium-catalyzed cross-coupling reaction, specifically a Heck reaction. The Heck reaction involves the coupling of an aryl halide (in this case, iodobenzene) with an alkene (here, acrylonitrile) in the presence of a palladium catalyst and a base.
Step 2: Analyze the reactants. The aryl halide (iodobenzene) will act as the electrophile, while the alkene (acrylonitrile) will act as the nucleophile. The palladium catalyst facilitates the formation of a carbon-carbon bond between the two reactants.
Step 3: Predict the regioselectivity. In the Heck reaction, the alkene typically undergoes substitution at the less sterically hindered position. For acrylonitrile, the substitution will occur at the terminal carbon of the double bond, as it is less hindered.
Step 4: Consider the stereochemistry. The Heck reaction often leads to the formation of the trans product due to the anti-addition mechanism of the palladium catalyst.
Step 5: Combine the pieces. The product will be a substituted alkene where the phenyl group from iodobenzene is attached to the terminal carbon of acrylonitrile, forming a trans-stilbene-like structure with the nitrile group intact.
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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 halide and an alkene, resulting in the formation of a substituted alkene. This reaction is significant in organic synthesis for constructing carbon-carbon bonds and is widely used in the pharmaceutical and materials industries. The reaction typically requires a base and a ligand to stabilize the palladium catalyst.
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Heck Reaction
Palladium Catalysis
Palladium catalysis involves the use of palladium as a catalyst to facilitate various organic reactions, including cross-coupling reactions like the Heck reaction. Palladium can exist in multiple oxidation states, allowing it to participate in different steps of the reaction mechanism, such as oxidative addition, transmetalation, and reductive elimination. The choice of ligands and reaction conditions can significantly influence the efficiency and selectivity of the reaction.
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Substitution Reactions
Substitution reactions involve the replacement of one functional group in a molecule with another. In the context of the Heck reaction, the aryl halide undergoes substitution where the halogen is replaced by an alkene moiety. Understanding the mechanisms of substitution reactions, including nucleophilic and electrophilic pathways, is crucial for predicting the products of reactions and designing synthetic routes in organic chemistry.
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Related Practice
Textbook Question
What reactants are needed to synthesize each of the following compounds using a Heck reaction?
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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:
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Textbook Question
What is the product of each of the following reactions?
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Textbook Question
What hydrocarbon would you use to prepare the organoboron compound in Problem 14?
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