Epoxide Reactants

alkene + mCPBA

syn epoxide synthesis stereospecific rxn that generates an epoxide and a carboxylic acid

alkene + [R]CO3H

epoxide synthesis stereospecific rxn that generates a racemic mix of enatiomers

alkane + halohydrin

forms an alkoxide used to generate epoxide

structure of an alkoxide

an organic group bonded to a negatively charged oxygen atom, written as RO− and often ionically bonded to a positively charged ion (like Na+)

structure of an epoxide

organic three-membered cyclic oxygen compounds

structure of a halohydrin

a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms

alkene + halogen, H2O

forms a halohydrin (with an OH group) to generate an alkoxide which helps generate an epoxide

epoxide + strong acid (H+), H2O

acid catalyzed ring opening rxn in which the acid attacks the more substituted carbon

structure of H2SO4

very strong acid

epoxide + strong base (OH-), H2O

base catalyzed ring opening rxn in which the strong nucleophile attacks the less substituted carbon

epoxide + alkoxide, alcohol

ring opening rxn that acts as a fully SN2 rxn

epoxide + H+, alcohol

ring opening rxn that acts as an "SN1-like" SN2 rxn

epoxide + strong nucleophile (no acid)

ring opening rxn that generates an alkyl with an alcohol group from the nucleophile attacking the less substituted carbon