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

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.

Key Concepts

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.