Ethers

H-Bonding in Ethers

Solvation

Crown Ethers Can Act as Phase Transfer Catalysts

Nomenclature

Alkene Oxides, Oxiranes or Epoxides

Several Naming Methods

Epoxide groups are Common in Biologically Active Molecules

A New Class of Anti-tumor Agents

Epoxides are Extremely Reactive

Williamson Ether Synthesis Preparation of Unsymmetrical Ethers

Williamson Ether Synthesis: SN2

Oxymercuration Hydration Markovnikov addition Regiospecific Reaction

Alkoxymercuration

Use an Alcohol Instead of H2O

Intramolecular Alkoxymercuration

Epoxide Preparation From Alkenes

Epoxide Preparation From Halohydrins

Mechanism

Propose a Mechanism

Reaction of Ethers

Unsymmetrical Ethers

Examples

Base Catalyzed Ring-Opening of Epoxides

Base Opens Ring from Unhindered Side

Grignard Reagents open Epoxides

Ring-Opening is Sterically Controlled

Acid Catalyzed Ring-Opening Aqueous and in Alcohol

Regiochemistry Ring Opens at More Hindered Site

Different Regiosomers

Why does Acid Catalyzed Opening Give Inversion?

Propose a Mechanism

2 Successive SN2 Reactions

Provide a Mechanism

Benzene Toxicity