Textbook Question
What is the product of each of the following reactions?
a.
5
views
Ch. 11 - Organometallic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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 17b
What is the product of each of the following reactions?
b. 
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a typical example of a cross-coupling reaction, specifically a Heck reaction. The Heck reaction involves the coupling of an aryl or vinyl halide (in this case, an aryl iodide) with an alkene in the presence of a palladium catalyst and a base.
Step 2: Identify the reactants. The aryl iodide is a substituted cyclopentene ring with an iodine atom attached. The alkene is a terminal alkene with a methyl group attached to the double bond.
Step 3: Understand the mechanism. In the Heck reaction, the palladium catalyst facilitates the oxidative addition of the aryl halide to form a palladium-aryl complex. The alkene then coordinates to the palladium center, followed by migratory insertion of the alkene into the palladium-aryl bond.
Step 4: Predict the regioselectivity. The alkene will couple with the aryl group at the less sterically hindered position, forming a new C-C bond. The product will be a substituted alkene where the aryl group is attached to the terminal carbon of the alkene.
Step 5: Consider stereochemistry. The Heck reaction typically proceeds with retention of the double bond geometry in the alkene. The final product will retain the E-configuration of the alkene unless otherwise specified.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organometallic Chemistry
Organometallic chemistry involves compounds containing metal-carbon bonds, where metals can be transition metals or main group elements. These compounds are crucial in various reactions, including cross-coupling reactions, where they facilitate the formation of carbon-carbon bonds. Understanding the role of organometallic reagents is essential for predicting the products of reactions involving these species.
Recommended video:
Guided course
02:50
Ruining Organometallics
Cross-Coupling Reactions
Cross-coupling reactions are a class of reactions in organic chemistry where two different organic groups are joined together using a metal catalyst. Common examples include the Suzuki and Heck reactions, which utilize palladium catalysts to couple aryl halides with alkenes or other nucleophiles. Recognizing the mechanism and conditions of these reactions is vital for determining the expected products.
Recommended video:
Guided course
03:22Cross-Coupling Reaction Mechanisms
Palladium Catalysis
Palladium catalysis is a key technique in organic synthesis, particularly in cross-coupling reactions. Palladium can exist in multiple oxidation states, allowing it to facilitate the transfer of groups between reactants. The choice of ligands and reaction conditions can significantly influence the efficiency and selectivity of the reaction, making it important to understand how these factors affect the outcome.
Recommended video:
2:31Nucleophilic Catalysis Concept 1
Related Practice
Textbook Question
What reactants are needed to synthesize each of the following compounds using a Heck reaction?
a.
1
views
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?
2
views
Textbook Question
Show how the Suzuki and/or Heck reactions can be used to prepare the following compounds:
a.
2
views
Textbook Question
What hydrocarbon would you use to prepare the organoboron compound in Problem 14?
1
views
Textbook Question
What products are obtained from metathesis of each of the following alkenes?
a. CH3CH2CH=CH2
1
views