Epoxide formation from alkene

 Epoxides or oxacyclopropanes can be obtained by

reaction so-called epoxidation from alkenes with peroxy
acids.
 The most commonly used peroxy acids are
 meta-chloroperoxybenzoic acid (MCPBA) and
 peroxyacetic acid.
Epoxidation from alkenes with Peroxy acids
 This reaction is stereospecific. If we start with cis-alkene we will
obtain cis-epoxide. The same applies to trans-isomers.
 Epoxides formation from halohydrins: Halohydrins treated
with strong base (such as hydroxide anion) can form
epoxides through with intramolecular SN2 reaction.

 Halohydrins treated with strong base (such as hydroxide

anion) can form epoxides through with intramolecular SN2
reaction.
 When alkenes treated with a halogen in the presence of
water they will be converted into halohydrins which can be
converted further into epoxides.
Mechanism of epoxide formation

 This process achieved via an Williamson ether synthesis.

Hydroxide deprotonates the halohydrin and an alkoxide
ion is formed.
 Then this ion acts as a nucleophile in an intramolecular
SN2 mechanism ejecting the bromide as a leaving group.