Question

Epoxide formation is stereospecific, whether it's accomplished by treating an alkene with peroxyacid or whether it's formed by using X2, H2O to make a halohydrin, which is treated with a strong base to do an intramolecular Williamson synthesis. Match each of the following epoxides with the alkene that was used as a starting material.

A) Provide the list of epoxides.
B) Identify the stereospecific method used for each epoxide.
C) Match each epoxide with the corresponding alkene.
D) Discuss the applications of stereospecific epoxide formation.

Answer 1

Stereospecific epoxide formation is a chemical reaction where alkenes are converted into oxiranes in a predictable manner, and these epoxides are useful as reactive intermediates in organic synthesis and as sterilizing agents.

Step-by-step explanation:

Stereospecific epoxide formation refers to the process where an alkene is converted to an oxirane, a three-membered cyclic ether, in a way that is predictable and consistent based on the stereochemistry of the starting material. This can be accomplished through direct epoxidation with a peroxyacid or through the halohydrin route by treating an alkene with X2, H2O to form a halohydrin, followed by an intramolecular Williamson synthesis with a strong base.

For example, treating ethylene (H2C=CH2) leads to the formation of a simple epoxide, ethylene oxide. In the context of organic synthesis, epoxides are valued for their high reactivity, making them useful as intermediates in creating a vast array of compounds. Oxiranes like 2-ethyl-3-methyloxirane, due to their angle strain from the deviation of bond angles to 60° from the typical 109.5°, are reactive and can serve as sterilizing agents due to their ability to interact quickly with the compounds in microorganisms.