Williamson Ether Synthesis

C₂H₅ONa + CH₃I → C₂H₅OCH₃ + NaI

Overview

Sodium ethoxide (an alkoxide) reacts with methyl iodide in an SN2 reaction to form ethyl methyl ether. This is the most general and reliable method for synthesizing asymmetric ethers. The alkoxide acts as the nucleophile, and a primary alkyl halide provides the best yields.

Everyday Example

MTBE (methyl tert-butyl ether), once the most widely used gasoline additive, was produced by a variation of ether synthesis.

Industrial Importance

Williamson synthesis is used to produce anisole, crown ethers, polyethylene glycol derivatives, and pharmaceutical ether linkages.

Properties

Type: Organic
Reversible: No
Energy: Exothermic
ΔH: -90.0 kJ/mol

Related Reactions

Aldol Condensation of Acetaldehyde Amide Formation (Acetic Acid + Ammonia) Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Bromination of Ethylene Buchwald-Hartwig Amination Cannizzaro Reaction of Formaldehyde Catalytic Hydrogenation of Ethylene Claisen Condensation (Ethyl Acetate) Condensation Polymerization (Nylon 6,6)

Frequently Asked Questions

What is the equation for Williamson Ether Synthesis?

The balanced equation is: C₂H₅ONa + CH₃I → C₂H₅OCH₃ + NaI.

What type of reaction is Williamson Ether Synthesis?

Williamson Ether Synthesis is a organic reaction.

Is Williamson Ether Synthesis exothermic or endothermic?

Williamson Ether Synthesis is exothermic (releases energy). The enthalpy change (ΔH) is -90.0 kJ/mol.