Core - Organic Chemistry

Chapter 11

Ethers, Epoxides, Sulfides

11.1 : Structure and Nomenclature of Ethers

11.1 : 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 — ...

11.2 : Physical Properties of Ethers

11.2 : 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 ...

11.3 : Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

11.3 : 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 ...

11.4 : Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

11.4 : 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 ...

11.5 : Ethers to Alkyl Halides: Acidic Cleavage

11.5 : 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, ...

11.6 : Autoxidation of Ethers to Peroxides and Hydroperoxides

11.6 : 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 ...

11.7 : Crown Ethers

11.7 : 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 ...

11.8 : Structure and Nomenclature of Epoxides

11.8 : 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 ...

11.9 : Preparation of Epoxides

11.9 : 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 ...

11.10 : Sharpless Epoxidation

11.10 : 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 ...

11.11 : Acid-Catalyzed Ring-Opening of Epoxides

11.11 : 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 ...

11.12 : Base-Catalyzed Ring-Opening of Epoxides

11.12 : 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 ...

11.13 : Structure and Nomenclature of Thiols and Sulfides

11.13 : 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 ...

11.14 : Preparation and Reactions of Thiols

11.14 : 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 ...

11.15 : Preparation and Reactions of Sulfides

11.15 : 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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