What does the epoxidation of trans-2-pentene produce?
The epoxidation of trans-pent-2-ene produces a racemic mixture of trans-pent-2-ene epoxide isomers.
The mechanism if the reaction is given here.
The addition is a concerted syn addition.
Groups that were cis in the original alkene remain cis in the product. Groups that were trans remain trans.
Compare the epoxidation of trans-but-2-ene.
If we replace a methyl group with ethyl, we see that the epoxidation of trans-pent-2-ene produces trans-pent-2-ene epoxide.
The product is chiral, so we get a 50:50 mixture of the two enantiomers.
The IUPAC name is (
Heterocyclic compounds are often named by the Hantzsch-Widman system:
- The oxygen atom is indicated by the prefix -oxa. It is automatically atom 1 in the ring, and the "a" is omitted before a vowel.
- The three-membered ring is indicated by the infix -ir (think tri).
- The saturated ring is indicated by the suffix -ane.
So a third name for this compound is (