Textbook Question
What bromo-substituted compound would be required to react with (CH2=CH)2CuLi in order to form each of the following compounds?
c.
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Ch. 11 - Organometallic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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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 8b
What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?
b. (CH3CH=CH)2CuLi
Verified step by step guidance1
Step 1: Understand the reaction mechanism. Ethylene oxide reacts with organocuprates (R2CuLi) via nucleophilic attack. The organocuprate acts as a nucleophile, attacking the less sterically hindered carbon of the ethylene oxide ring, leading to ring opening.
Step 2: Identify the nucleophile in the given organocuprate. The organocuprate provided is (CH3CH=CH)2CuLi, which contains two allyl groups (CH3CH=CH). These allyl groups are the nucleophilic species that will attack the ethylene oxide.
Step 3: Predict the product of the nucleophilic attack. One of the allyl groups (CH3CH=CH) will attack the less hindered carbon of the ethylene oxide, breaking the three-membered ring and forming a new C-C bond. This results in an intermediate alkoxide.
Step 4: Consider the role of acid in the reaction. After the nucleophilic attack, the intermediate alkoxide is protonated by the addition of acid (e.g., H3O+), converting the alkoxide into an alcohol.
Step 5: Write the structure of the final product. The final product will be an alcohol where the allyl group (CH3CH=CH) is attached to one of the carbons of the ethylene oxide, and the other carbon of the ethylene oxide becomes part of the hydroxyl (-OH) group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ethylene Oxide Reactivity
Ethylene oxide is a cyclic ether that reacts with nucleophiles due to its strained ring structure. When it undergoes ring-opening reactions, it can form alcohols. The nucleophile attacks the less hindered carbon atom, leading to the formation of a primary alcohol after subsequent protonation.
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Reagents used to oxidize Sulfides.
Organocuprates
Organocuprates, such as (CH3CH=CH)2CuLi, are organometallic compounds that act as nucleophiles in organic reactions. They are derived from lithium diorganocopper reagents and are known for their ability to add to electrophiles, such as carbonyls or epoxides, facilitating the formation of new carbon-carbon bonds.
Acid-Catalyzed Protonation
After the nucleophilic attack on ethylene oxide, the resulting alkoxide intermediate can be protonated by an acid. This step is crucial as it converts the alkoxide into a stable alcohol. The choice of acid can influence the reaction's efficiency and the final product's structure.
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Related Practice
Textbook Question
What are the products of the following reactions?
a.
3
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Textbook Question
What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?
c.
1
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Textbook Question
What bromo-substituted compound would be required to react with (CH2=CH)2CuLi in order to form each of the following compounds?
b.
1
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Textbook Question
Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?
1
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Textbook Question
How could the following compounds be prepared, using cyclohexene as a starting material?
a.
3
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