|Chapter 16: Ethers, Epoxides and Sulfides|
Synthesis of Ethers via Acid-catalysed Condensation of Alcohols
Reaction type: Nucleophilic Substitution (SN2)
An acid/base reaction. Protonation of the alcoholic oxygen to make a better leaving group. This step is very fast and reversible. The lone pairs on the oxygen make it a Lewis base.
The O of the second alcohol molecule functions as the nucleophile and attacks to displace the good leaving group, a neutral water molecule, by cleaving the C-O bond. This creates an oxonium ion intermediate.
Another acid / base reaction. The proton is removed by a suitable base (here a water molecule, ROH is another alternative) to give the ether product.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|