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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.02%3A_Preparing_EthersThere are several methods for preparing ethers and the two most popular are the Williamson ether synthesis and the alkoxymercuration-demercuration. The Williamson synthesis involves reacting an alkoxi...There are several methods for preparing ethers and the two most popular are the Williamson ether synthesis and the alkoxymercuration-demercuration. The Williamson synthesis involves reacting an alkoxide ion with a primary alkyl halide, resulting in ether formation. Alkoxymercuration-demercuration provides an alternative route by using alcohols with alkenes and mercuric acetate. Both methods are commonly used to produce ethers, which serve as solvents or intermediates in reactions.
- https://chem.libretexts.org/Ancillary_Materials/Reference/Organic_Chemistry_Glossary/Williamson_Ether_SynthesisWilliamson ether synthesis is a method of preparation of ethers. It is a nucleophilic aliphatic substitution at saturated carbon in which the nucleophile is either an alkoxide ion or a phenoxide ion.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.03%3A_Preparing_EthersFor example, tert-butyl methyl ether, a substance used in the 1990s as an octane booster in gasoline, is best prepared by reaction of tert-butoxide ion with iodomethane rather than by reaction of meth...For example, tert-butyl methyl ether, a substance used in the 1990s as an octane booster in gasoline, is best prepared by reaction of tert-butoxide ion with iodomethane rather than by reaction of methoxide ion with 2-chloro-2-methylpropane. The reaction is initiated by electrophilic addition of Hg 2+ to the alkene, followed by reaction of the intermediate cation with alcohol and reduction of the C–Hg bond by NaBH 4 . A variety of alcohols and alkenes can be used in alkoxymercuration.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/03%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/3.03%3A_Preparing_EthersWe studied oxymercuration as a method of converting an alkene to an alcohol in the Alkene Reactions Chapter. “Alkoxymercuration” is a very similar process, except that we are now converting an alkene ...We studied oxymercuration as a method of converting an alkene to an alcohol in the Alkene Reactions Chapter. “Alkoxymercuration” is a very similar process, except that we are now converting an alkene into an ether. Review the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.02%3A_Preparing_EthersReview the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction. Note that the alcohol reactant is used as...Review the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction. Note that the alcohol reactant is used as the solvent, and a trifluoroacetate mercury (II) salt is used in preference to the mercuric acetate (trifluoroacetate anion is a poorer nucleophile than acetate).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Ethers/Synthesis_of_Ethers/Williamson_Ether_SynthesisThe Williamson Ether synthesis is the easiest, and perhaps the fastest, way to create ethers.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Organic_Chemistry_with_a_Biological_Emphasis_(SUNY_Oneonta)/08%3A_Nucleophilic_Substitution_Reactions/8.09%3A_Nucleophilic_substitution_in_the_LabSynthetic organic chemists often make use of a reaction that is conceptually very similar to the SAM-dependent methylation reactions we saw earlier. The 'Williamson ether synthesis' is named for Alexa...Synthetic organic chemists often make use of a reaction that is conceptually very similar to the SAM-dependent methylation reactions we saw earlier. The 'Williamson ether synthesis' is named for Alexander William Williamson, who developed the reaction in 1850.
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/03%3A_Alcohols_and_Ethers/3.01%3A_Preparing_EthersIn the second step, a second alcohol displaces water from the protonated alcohol during an S N 2 reaction yielding a protonated ether. One important procedure, known as the Williamson Ether Synthesis,...In the second step, a second alcohol displaces water from the protonated alcohol during an S N 2 reaction yielding a protonated ether. One important procedure, known as the Williamson Ether Synthesis, proceeds by an S N 2 reaction of an alkoxide nucleophile with a primary alkyl halide or tosylate. Analysis: The ether is asymmetrical so each of the C-O bonds can be broken to create a different set of possible reactants.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/04%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/4.03%3A_Preparing_EthersNote that the alcohol reactant is used as the solvent, and a trifluoroacetate mercury (II) salt is used in preference to the mercuric acetate (trifluoroacetate anion is a poorer nucleophile than aceta...Note that the alcohol reactant is used as the solvent, and a trifluoroacetate mercury (II) salt is used in preference to the mercuric acetate (trifluoroacetate anion is a poorer nucleophile than acetate). Review the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction.
- https://chem.libretexts.org/Courses/Smith_College/CHM_222_Chemistry_II%3A_Organic_Chemistry_(2025)/10%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/10.03%3A_Preparing_Ethers_(CHM_223)Review the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction. Note that the alcohol reactant is used as...Review the mechanism of the oxymercuration reaction in Section 8.5, paying particular attention to the regiochemistry and the stereochemistry of the reaction. Note that the alcohol reactant is used as the solvent, and a trifluoroacetate mercury (II) salt is used in preference to the mercuric acetate (trifluoroacetate anion is a poorer nucleophile than acetate).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)/08%3A_Nucleophilic_Substitution_Reactions/8.09%3A_Nucleophilic_substitution_in_the_LabSynthetic organic chemists often make use of a reaction that is conceptually very similar to the SAM-dependent methylation reactions we saw earlier. The 'Williamson ether synthesis' is named for Alexa...Synthetic organic chemists often make use of a reaction that is conceptually very similar to the SAM-dependent methylation reactions we saw earlier. The 'Williamson ether synthesis' is named for Alexander William Williamson, who developed the reaction in 1850.
