Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄
(k)

검증된 단계별 안내

Identify the reaction type: The given reagents, Hg(OAc)₂, H₂O followed by NaBH₄, indicate an oxymercuration-demercuration reaction. This reaction is used to hydrate alkenes (add H and OH) without carbocation rearrangement.

Determine the regioselectivity: Oxymercuration-demercuration follows Markovnikov's rule, meaning the OH group will add to the more substituted carbon of the double bond, while the H will add to the less substituted carbon.

Analyze the alkene structure: Examine the position of the double bond in the given alkene. Identify the more substituted carbon (the carbon with more alkyl groups attached) and the less substituted carbon.

Predict the intermediate: In the first step, Hg(OAc)₂ reacts with the alkene to form a mercurinium ion intermediate. Water (H₂O) then attacks the more substituted carbon, leading to the addition of an OH group.

Complete the reaction: In the second step, NaBH₄ reduces the intermediate, replacing the mercury group with a hydrogen atom. The final product is an alcohol with the OH group on the more substituted carbon and the H on the less substituted carbon.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of reactions involving alkenes, guiding the formation of more stable carbocations during the reaction.

Oxymercuration-Demercuration

Oxymercuration-Demercuration is a two-step reaction process used to convert alkenes into alcohols. The first step involves the addition of mercuric acetate (Hg(OAc)₂) and water, which forms a mercurial intermediate. The second step, using sodium borohydride (NaBH₄), reduces the intermediate to yield the corresponding alcohol without rearrangement, ensuring the product follows Markovnikov's Rule.

Hydration of Alkenes

Hydration of alkenes refers to the addition of water across the double bond of an alkene, resulting in the formation of alcohols. This reaction can occur via acid-catalyzed mechanisms or through oxymercuration-demercuration, and it is crucial for synthesizing alcohols from alkenes while maintaining regioselectivity and stereochemistry.

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)2 , H2O 2. NaBH4 (k)