What physical properties of epoxides make them useful in organic synthesis?
Epoxides are an important class of compounds in organic synthesis, because nucleophilic ring opening takes place easily in an SN2 pathway with inversion of configuration at the reacting carbon center. The driving force of the high reactivity is the inherent strain of the three-membered heterocycle.
What are the two methods of synthesizing epoxides?
There’s two important ways to make epoxides from alkenes, one “direct” and one “indirect”. Let’s review the first method. Treating an alkene with a “peroxyacid” (that’s a carboxylic acid containing an extra oxygen) leads to direct formation of an epoxide.
What are epoxides in organic chemistry?
epoxide, cyclic ether with a three-membered ring. The basic structure of an epoxide contains an oxygen atom attached to two adjacent carbon atoms of a hydrocarbon. The strain of the three-membered ring makes an epoxide much more reactive than a typical acyclic ether.
What does epoxide do in a reaction?
Under aqueous basic conditions the epoxide is opened by the attack of hydroxide nucleophile during an SN2 reaction. The epoxide oxygen forms an alkoxide which is subsequently protonated by water forming the 1,2-diol product.
What is epoxide example?
A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called “oxirane”.
Are epoxide reactions racemic?
If an achiral epoxide is the starting material, then a racemic mixture of enantiomers is formed because the two carbons of the epoxide ring are equivalent and attacked by the nucleophile at the same rate.
What is an ether organic chemistry?
ether, any of a class of organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. Ethers are similar in structure to alcohols, and both ethers and alcohols are similar in structure to water.