Textbook Question
What products would you expect from the following coupling reactions?
(c)
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Ch. 17 - Reactions of Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 55b
What products would you expect from the following coupling reactions?
(b) 
Verified step by step guidance1
Step 1: Identify the type of coupling reaction. The reaction involves a palladium catalyst (PdCl₂), which suggests it is a Heck reaction. The Heck reaction typically couples an aryl halide (such as an aryl iodide) with an alkene or an unsaturated compound.
Step 2: Analyze the reactants. The aryl iodide has an iodine atom attached to a benzene ring with a ketone group at the para position. The second reactant is acrylic acid, which contains a double bond and a carboxylic acid functional group.
Step 3: Determine the regioselectivity of the Heck reaction. The palladium catalyst facilitates the coupling of the aryl group to the double bond of acrylic acid. The aryl group will attach to the less substituted carbon of the double bond, following the typical regioselectivity of the Heck reaction.
Step 4: Predict the product structure. The aryl group from the aryl iodide will bond to the terminal carbon of the double bond in acrylic acid, forming a new C-C bond. The double bond in acrylic acid will shift to form a conjugated system with the benzene ring.
Step 5: Verify the stereochemistry. The Heck reaction generally produces the trans product due to the anti addition mechanism. Ensure the product reflects this stereochemical outcome.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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. These reactions often involve the formation of carbon-carbon bonds and are crucial for synthesizing complex organic molecules. Common examples include the Suzuki and Heck reactions, which utilize palladium as a catalyst to facilitate the coupling of aryl halides with various nucleophiles.
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Cross-Coupling Reaction Mechanisms
Palladium Catalysis
Palladium catalysis is a key technique in organic synthesis, particularly in cross-coupling reactions. Palladium serves as a versatile catalyst that can activate both the organic halide and the nucleophile, allowing for efficient bond formation. The use of palladium complexes, such as PdCl2, enables the reaction to proceed under milder conditions and with greater selectivity, making it a valuable tool in the synthesis of pharmaceuticals and other complex molecules.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is essential for modifying aromatic compounds and can lead to the formation of various functional groups. In the context of the provided reaction, the presence of an iodine substituent on the aromatic ring enhances its reactivity, facilitating the coupling with the nucleophile through the EAS mechanism.
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Related Practice
Textbook Question
Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.
(b)
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Textbook Question
What products would you expect from the following coupling reactions?
(a)
1
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Textbook Question
Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.
(c)
1
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Textbook Question
What products would you expect from the following coupling reactions?
(d)
(e)
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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?
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