Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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1:39 minutes

Problem 8b

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

Verified step by step guidance

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.

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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b. (CH₃CH₂)₂CuLi followed by H₃O⁺

Textbook Question

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an α-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

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Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(d) cyclopentyl propyl ketone

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Show how you would accomplish the following synthetic

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(c)

(d)

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What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?b. (CH3CH=CH)2CuLi

Key Concepts

Ethylene Oxide Reactivity

Organocuprates

Acid-Catalyzed Protonation

Watch next

What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?
b. (CH₃CH=CH)₂CuLi