Textbook Question
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(f) trans-2,3-epoxyoctane from octan-2-ol
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12. Alcohols, Ethers, Epoxides and Thiols
Making Ethers - Cumulative Practice
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Predict the product of the following reaction.
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Verified step by step guidance1
Identify the reaction type: The reaction involves an alkene and is treated with mercuric trifluoroacetate (Hg(O2CCF3)2) followed by sodium borohydride (NaBH4) and sodium hydroxide (NaOH). This is an oxymercuration-demercuration reaction.
Understand the mechanism: Oxymercuration-demercuration is a two-step process. In the first step, the alkene reacts with mercuric trifluoroacetate to form a mercurinium ion intermediate. In the second step, NaBH4 reduces the intermediate, replacing the mercury with a hydrogen atom.
Predict the regioselectivity: Oxymercuration-demercuration follows Markovnikov's rule, where the hydroxyl group (OH) will add to the more substituted carbon of the double bond.
Consider stereochemistry: This reaction typically proceeds with anti-addition, meaning the OH group and the hydrogen added in the reduction step will be on opposite sides of the former double bond.
Determine the product: The final product will have the OH group on the more substituted carbon of the original alkene, with the stereochemistry reflecting anti-addition. Analyze the given options to identify the structure that matches these criteria.
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