Ch. 18 Ethers & Epoxides; Thiols & Sulfides

Williamson Ether Synthesis

R’ must be primary or methyl to favor substitution over elimination

Alkoxymercuration-Demercuration

Acidic Cleavage of an Ether

Autooxidation of Ethers

Epoxide formation from halohydrins

halohydrin is treated with a base, the -OH is deprotonated to give an alkoxide. The alkoxide undergoes a kind of intramolecular Sn2, where the O^- attacks the carbon bonded to the halogen group, forming an epoxide

Epoxide Ring Opening using a nucleophile under basic conditions

the nucleophile always adds to the less substituted carbon

Epoxide Ring Opening using a nucleophile under acidic conditions

the nucleophile adds to the more substitution carbon if the substrate is a tertiary carbon, it adds to the less substituted carbon if the substrate is a primary or secondary carbon.

Oxidation of Thiols

Sulfide formation from Thiols

Epoxide formation from an alkene

Reagent: RCO₃H (like mCPBA)