Chapter 11
Ethers, Epoxides, Sulfides
![Structure and Nomenclature of Ethers](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11685.jpg)
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different…
![Physical Properties of Ethers](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11722.jpg)
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 Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11740.jpg)
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
The acid-catalyzed…
![Ethers to Alkyl Halides: Acidic Cleavage](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11741.jpg)
Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and,…
![Crown Ethers](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11787.jpg)
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized…
![Structure and Nomenclature of Epoxides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/11932.jpg)
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…
![Sharpless Epoxidation](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12108.jpg)
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless…
![Acid-Catalyzed Ring-Opening of Epoxides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12109.jpg)
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from…
![Structure and Nomenclature of Thiols and Sulfides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12111.jpg)
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols…
![Preparation and Reactions of Thiols](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12112.jpg)
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance,…
![Nanosponge Tunability in Size and Crosslinking Density](https://cloudfront.jove.com/files/thumbs/56073_t.png)
We describe a protocol for the synthesis of linear polyesters containing pendant epoxide functionality and their incorporation into a nanosponge with…
![Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework](https://cloudfront.jove.com/files/thumbs/57455_t.png)
We present a method for preparing thioester molecules as the masked form of the thiol linkers and their utilization for accessing a semiconducting…