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11-07-08 - o Acid catalyzed alkene hydration is a...

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318M – Krische, Lecture 32: F - 11/07/08, Ethers, Sulfides and Epoxides Today, we begin Ethers, sulfides and epoxides. We commence with a brief discussion covering the physical properties of ethers. Preparation of Ethers-Williamson Ether Synthesis (SN2) : We have already encountered a number of methods for the preparation of ethers. One of the most famous methods is the “Williamson Ether Synthesis.” This is nothing more than an SN2 reaction involving the addition of an alkoxide nucleophile to a primary halide. Only primary halides work well in this reaction. Secondary halides provide E2 products as the major reaction products. Preparation of Ethers-SN1 Type Reactions : As previously seen in chapter 8, tertiary halides participate in solvolysis reactions in alcoholic media to afford ethers. Preparation of Ethers-Alkene Hydration Using Alcohols as Nucleophiles
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Unformatted text preview: : o Acid catalyzed alkene hydration is a transformation that we have covered earlier. If we use an alcohol instead of water to perform this hydration, ethers are produced in good yields. This reaction is limited to alkenes that can form stable carbocations upon protonation and primary alcohols (which are resistant to dehydration). o Oxymercuration of alkenes is another transformation that we have covered in Chapter 6. Here, we can again substitute an alcohol for water, thus obtaining ether products. • Preparation of Ethers-Acid Catalyzed Condensation of Primary Alcohols : Finally, we learned that exposure of primary alcohols to catalytic acid results in the formation of ether products through an SN2 type pathway. This method is limited to the preparation of symmetric ethers....
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