Textbook Question
What products would you expect from the following coupling reactions?
(c)
2
views
Ch. 17 - Reactions of Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 17, Problem 55d,e
What products would you expect from the following coupling reactions?
(d) 
(e) 
Verified step by step guidance1
Step 1: Identify the type of coupling reaction. The first reaction involves a bromobenzene derivative and a boronic ester, which suggests a Suzuki coupling reaction. The second reaction involves a bromonaphthalene derivative and a nitro-substituted styrene, which suggests a Heck coupling reaction.
Step 2: For the Suzuki coupling reaction, the palladium catalyst facilitates the cross-coupling between the aryl bromide and the boronic ester. The base activates the boronic ester, allowing it to react with the aryl bromide. The product will be a new C-C bond formed between the phenyl group and the alkene chain attached to the boron.
Step 3: For the Heck coupling reaction, the palladium catalyst and base facilitate the formation of a C-C bond between the aryl bromide and the alkene. The nitro-substituted styrene will couple with the bromonaphthalene derivative, forming a new C-C bond at the β-position of the alkene relative to the nitro group.
Step 4: Consider regioselectivity and stereochemistry. In the Suzuki reaction, the product will retain the stereochemistry of the alkene in the boronic ester. In the Heck reaction, the product will likely favor the trans configuration of the alkene due to steric and electronic factors.
Step 5: Write the final structures of the products. For the Suzuki reaction, the product will be a phenyl group attached to the alkene chain. For the Heck reaction, the product will be a naphthalene group attached to the β-position of the nitro-substituted styrene alkene.
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.
Coupling Reactions
Coupling reactions are organic reactions where two fragments are joined together, typically involving the formation of a new carbon-carbon bond. These reactions are crucial in organic synthesis, particularly in the formation of complex molecules. Common types include Suzuki, Heck, and Sonogashira reactions, each utilizing different reagents and conditions to achieve the desired product.
Recommended video:
Guided course
02:54
Sonogashira Coupling Reaction
Reactivity of Functional Groups
Understanding the reactivity of functional groups is essential in predicting the outcomes of coupling reactions. Different functional groups, such as halides, alcohols, and amines, have distinct reactivity patterns that influence how they participate in reactions. Recognizing these patterns helps in determining which groups can effectively couple and what products will form.
Recommended video:
Guided course
02:36Identifying Functional Groups
Mechanism of Reactions
The mechanism of a reaction outlines the step-by-step process by which reactants are converted into products. In coupling reactions, mechanisms often involve the formation of intermediates and the breaking and forming of bonds. A clear understanding of these mechanisms allows chemists to predict reaction outcomes and optimize conditions for desired products.
Recommended video:
Guided course
02:16Heck Reaction Mechanism
Related Practice
Textbook Question
Give the structures of compounds A through B in the following series of reactions.
2
views
Textbook Question
What products would you expect from the following coupling reactions?
(a)
1
views
Textbook Question
What products would you expect from the following coupling reactions?
(b)
2
views
Textbook Question
Give the structures of compounds A through C in the following series of reactions.
2
views
Textbook Question
A student added 3-phenylpropanoic acid (PhCH2CH2COOH) to a molten salt consisting of a 1:1 mixture of NaCl and AlCl3 maintained at 170 °C. After 5 minutes, he poured the molten mixture into water and extracted it into dichloromethane. Evaporation of the dichloromethane gave a 96% yield of the product whose spectra follow. The mass spectrum of the product shows a molecular ion at m/z 132. What is the product?
<IMAGE>
1
views