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.
1559
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 37d
What are the products of the following reactions?
d. 
Verified step by step guidance1
Step 1: Analyze the starting material and reagents. The starting material is an aryl iodide (1-iodo-4-ethylbenzene). The reaction involves three steps: (1) treatment with lithium (Li), (2) reaction with a borate ester (B(OR)3), and (3) a Suzuki coupling reaction with a vinyl bromide in the presence of Pd(PPh3)4 and Na2CO3 under heat.
Step 2: In the first step, lithium reacts with the aryl iodide to form an aryl lithium intermediate. This is a nucleophilic species where the iodine atom is replaced by lithium.
Step 3: In the second step, the aryl lithium intermediate reacts with the borate ester (B(OR)3) to form an aryl boronic ester. This is a key intermediate for Suzuki coupling reactions.
Step 4: In the third step, the aryl boronic ester undergoes a Suzuki coupling reaction with the vinyl bromide. The palladium catalyst (Pd(PPh3)4) facilitates the cross-coupling between the aryl group and the vinyl group, forming a new C-C bond.
Step 5: The final product is a styrene derivative where the aryl group (4-ethylphenyl) is connected to the vinyl group (CH=CH2). This product is formed through the combination of the aryl boronic ester and the vinyl bromide.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
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 a boronic acid or boronate ester with an organic halide in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds and is characterized by its mild reaction conditions and high functional group tolerance.
Recommended video:
Guided course
04:02
Suzuki Reaction
Organoboron Compounds
Organoboron compounds, such as boronic acids and boronate esters, are key intermediates in various organic reactions, including the Suzuki reaction. They contain a boron atom bonded to a carbon atom, which can participate in nucleophilic substitution reactions. Their ability to form stable complexes with transition metals makes them essential for cross-coupling reactions, facilitating the formation of new carbon-carbon bonds.
Recommended video:
Guided course
01:40Defining meso compounds.
Palladium Catalysis
Palladium catalysis plays a crucial role in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the oxidative addition of the organic halide and the subsequent reductive elimination to form the desired product. The use of palladium allows for lower activation energy and increased reaction rates, making it a preferred choice in synthetic organic chemistry.
Recommended video:
2:31Nucleophilic Catalysis Concept 1
Related Practice
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
views
Textbook Question
Using ethynylcyclohexane as a starting material and any other needed reagents, how can the following compounds be synthesized?
a.
3606
views
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
views
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:
c.
1080
views
Textbook Question
What are the products of the following reactions?
b.
1034
views