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 8c
What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?
c. 
Verified step by step guidance1
Step 1: Understand the reaction mechanism. Ethylene oxide is an epoxide, a three-membered cyclic ether, which is highly reactive due to ring strain. Organocuprates (R₂CuLi) are nucleophiles that can open the epoxide ring via an SN2 mechanism, attacking the less substituted carbon of the epoxide.
Step 2: Identify the nucleophile. In this case, the organocuprate (R₂CuLi) provides an alkyl group (R⁻) that acts as the nucleophile. The nucleophile will attack the less hindered carbon of the ethylene oxide, breaking the C-O bond and opening the ring.
Step 3: Write the intermediate product. After the nucleophilic attack, the oxygen atom from the ethylene oxide will carry a negative charge, forming an alkoxide ion (R-CH₂-CH₂-O⁻).
Step 4: Add acid to the reaction. The alkoxide ion is then protonated by the addition of acid (H⁺), resulting in the formation of an alcohol. The final product will be R-CH₂-CH₂-OH, where R is the alkyl group from the organocuprate.
Step 5: Generalize the products. For each specific organocuprate, substitute the R group into the final alcohol structure (R-CH₂-CH₂-OH). For example, if the organocuprate is (CH₃)₂CuLi, the product will be CH₃-CH₂-CH₂-OH.
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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 is highly reactive due to its strained three-membered ring structure. When it reacts with nucleophiles, such as organocuprates, it undergoes ring-opening to form alcohols. Understanding this reactivity is crucial for predicting the products formed in the reaction.
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Reagents used to oxidize Sulfides.
Organocuprates
Organocuprates are organometallic compounds containing copper, typically used as nucleophiles in organic synthesis. They are formed by the reaction of lithium diorganocopper reagents with alkyl or aryl halides. Their ability to react with electrophiles, like ethylene oxide, is essential for forming new carbon-carbon bonds and generating alcohols.
Acid Workup
An acid workup is a common step in organic reactions that involves adding an acid to protonate intermediates or products, often to neutralize bases or to facilitate the formation of alcohols from alkoxides. In the context of the reaction with ethylene oxide, the acid workup helps to convert the alkoxide formed after nucleophilic attack into the corresponding alcohol.
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Related Practice
Textbook Question
What are the products of the following reactions?
a.
1190
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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?
b. (CH3CH=CH)2CuLi
730
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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.
780
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Textbook Question
How could the following compounds be prepared, using cyclohexene as a starting material?
d.
1058
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Textbook Question
How could the following compounds be prepared, using cyclohexene as a starting material?
a.
954
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