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Chapter 11

Ethers, Epoxides, Sulfides

Structure and Nomenclature of Ethers
Structure and Nomenclature of Ethers
Structure and Bonding Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — ...
Physical Properties of Ethers
Physical Properties of Ethers
Overview An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of ...
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Overview Ethers can be prepared from organic compounds by various methods. Some of them are discussed below, Preparation of Ethers by Alcohol Dehydration ...
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Overview Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration. Preparation of ...
Ethers to Alkyl Halides: Acidic Cleavage
Ethers to Alkyl Halides: Acidic Cleavage
Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, ...
Autoxidation of Ethers to Peroxides and Hydroperoxides
Autoxidation of Ethers to Peroxides and Hydroperoxides
Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when ...
Crown Ethers
Crown Ethers
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by ...
Structure and Nomenclature of Epoxides
Structure and Nomenclature of Epoxides
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms ...
Preparation of Epoxides
Preparation of Epoxides
Overview Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin ...
Sharpless Epoxidation
Sharpless Epoxidation
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The ...
Acid-Catalyzed Ring-Opening of Epoxides
Acid-Catalyzed Ring-Opening of Epoxides
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the ...
Base-Catalyzed Ring-Opening of Epoxides
Base-Catalyzed Ring-Opening of Epoxides
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of ...
Structure and Nomenclature of Thiols and Sulfides
Structure and Nomenclature of Thiols and Sulfides
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are ...
Preparation and Reactions of Thiols
Preparation and Reactions of Thiols
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane ...
Preparation and Reactions of Sulfides
Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups ...
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