Domanda del libro di testo
What vinylic halide couples with styrene (C6H5-CH=CH2) in order to synthesize each of the following compounds using a Heck reaction?
c.
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Ch. 11 - Organometallic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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
Capitolo 11, Problema 33a,b
What are the products of the following reactions?
a. 
b. 
Guida verificata passo dopo passo1
Step 1: Analyze the starting material, which is an alkyl bromide (CH3CH2CH2Br). This compound contains a bromine atom attached to a propyl chain.
Step 2: The first reagent, lithium (Li), reacts with the alkyl bromide to form an organolithium compound (CH3CH2CH2Li). This is a nucleophilic species formed by replacing the bromine atom with lithium.
Step 3: The second reagent, copper(I) iodide (CuI), reacts with the organolithium compound to form a Gilman reagent (CH3CH2CH2)2CuLi. Gilman reagents are useful for coupling reactions.
Step 4: The third step involves the reaction of the Gilman reagent with the alkyl bromide provided in the reaction scheme (CH2=CHCH2Br or CH2=CHCHBrCH3). This is a coupling reaction where the Gilman reagent replaces the bromine atom in the alkyl bromide with the alkyl group from the Gilman reagent.
Step 5: The final product is formed by combining the alkyl group from the Gilman reagent with the alkyl bromide, resulting in a new carbon-carbon bond. The specific product depends on the structure of the alkyl bromide used in the third step.
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Organolithium Reagents
Organolithium reagents, such as those formed from lithium and organic halides, are highly reactive compounds used in organic synthesis. They act as strong nucleophiles, facilitating the formation of carbon-carbon bonds by attacking electrophiles. In the given reaction, lithium likely helps to generate a lithium alkyl intermediate that can further react with copper(I) iodide.
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01:52
Reagents
Cuprate Reagents
Cuprate reagents, formed from the reaction of organolithium compounds with copper(I) halides, are important in organic synthesis for their ability to participate in nucleophilic substitutions. They can react with alkyl halides to form new carbon-carbon bonds, allowing for the construction of more complex molecules. The use of CuI in the reaction indicates a pathway to generate a new alkyl group.
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01:52Reagents
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group (like bromine) by a nucleophile. In this context, the organolithium and cuprate reagents act as nucleophiles that attack the carbon atom bonded to the bromine, leading to the formation of new carbon-carbon bonds. Understanding the mechanism of these reactions is crucial for predicting the products of the given transformations.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
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