Making Ethers - Williamson Ether Synthesis

There are 4 major methods to create ethers. Most of these should look familiar in some way since they are variations of reactions we have used before. 

Williamson Ether Synthesis

The name given for the SN2 substitution of an oxide with an alkyl halide.

  • Only works with 0°, 1° alkyl halides since 2° and 3° alkyl halides will favor E2

Acid-Catalyzed Alcohol Condensation

Condensation reactions join two smaller molecules together to form a single, larger molecule.

  • Only forms symmetrical ethers

Alkoxymercuation-Reduction

Same reagents as oxymercuration, except with alcohol as the nucleophile instead of water.

Acid-Catalyzed Alkoxylation

Same reagents as acid-catalyzed hydration, except with alcohol as the nucleophile instead of water.

Example: Predict the product of the following reaction. 

4m

Example: Predict the product of the following reaction. 

6m