Chapter 16: Ethers, Epoxides and Sulfides

In contrast to alcohols, ethers are fairly unreactive except to very strong acids such as HI or HBr.
This low reactivity makes them useful as solvents, e.g. diethyl ether, Et₂O and tetrahydrofuran (THF), C₄H₈O.
Epoxides are more reactive than simple ethers due to the inherent ring strain and react with nucleophiles resulting in ring opening:

• Nomenclature
• Physical Properties
• Structure
• Reactivity
• Crown ethers

• Acid catalysed coupling of Alcohols
• Williamson Ether Synthesis

• Reaction with HI and HBr

• Nomenclature
• Properties
• Structure
• Reactivity

• Epoxidation of Alkenes
• Intramolecular Substitution of Halohydrins

• Overview
• Reactions of Epoxides under "basic" conditions
• Reactions of Epoxides under "acidic" conditions
• Epoxide Questions

• IR
• 1H NMR
• 13C NMR
• UV-Vis
• Mass Spectroscopy

• Nomenclature
• Structure
• Reactivity
• Preparation of Sulfides
• Reactions of Sulfides

• Sample Problems
• More practice problems
• Reaction Drills