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- https://chem.libretexts.org/Courses/can/CHEM_231%3A_Organic_Chemistry_I_Textbook/08%3A_Alkenes-_Reactions_and_Synthesis/8.08%3A_Hydration_of_Alkenes_-_Addition_of_HO_by_OxymercurationThe reaction is initiated by electrophilic addition of Hg 2 + (mercuric) ion to the alkene to give an intermediate mercurinium ion, whose structure resembles that of a bromonium ion (Figure \(\PageInd...The reaction is initiated by electrophilic addition of Hg 2 + (mercuric) ion to the alkene to give an intermediate mercurinium ion, whose structure resembles that of a bromonium ion (Figure \(\PageIndex{1}\)). Note that the regiochemistry of the reaction corresponds to Markovnikov addition of water; that is, the −OH group attaches to the more highly substituted carbon atom, and the −H attaches to the less highly substituted carbon.
- 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/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/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_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/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/Bookshelves/Organic_Chemistry/Organic_Chemistry_I_(Morsch_et_al.)/08%3A_Alkenes-_Reactions_and_Synthesis/8.04%3A_Hydration_of_Alkenes_-_Addition_of_HO_by_OxymercurationElectrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appro...Electrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appropriate temperatures to break the alkene's double bond. After a carbocation is formed, water bonds with the carbocation to form a 1º, 2º, or 3º alcohol on the alkane.
- https://chem.libretexts.org/Courses/Smith_College/CHM_222_Chemistry_II%3A_Organic_Chemistry_(2025)/15%3A_Alkenes-_Reactions_and_Synthesis/15.05%3A_Hydration_of_Alkenes_-_Addition_of_HO_by_OxymercurationElectrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appro...Electrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appropriate temperatures to break the alkene's double bond. After a carbocation is formed, water bonds with the carbocation to form a 1º, 2º, or 3º alcohol on the alkane.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/08%3A_Alkenes-_Reactions_and_Synthesis/8.05%3A_Hydration_of_Alkenes_-_Addition_of_HO_by_OxymercurationElectrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appro...Electrophilic hydration is the act of adding electrophilic hydrogen from a non-nucleophilic strong acid (a reusable catalyst, examples of which include sulfuric and phosphoric acid) and applying appropriate temperatures to break the alkene's double bond. After a carbocation is formed, water bonds with the carbocation to form a 1º, 2º, or 3º alcohol on the alkane.
