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Williamson Ether Synthesis

an alkoxide Nu attacks an alkyl halide to give the ether

Reaction type: Nucleophilic Substitution (SN2)

Summary

QUESTIONS
What reaction is likely to interfere if the halide is tertiary ?ANSWER
Can you write a balanced equation for the reaction of sodium metal with the alcohol ? ANSWER
What is the oxidation state and charge of the sodium metal ? ANSWER
What makes the methyl and primary halides most suitable ? ANSWER

Related Reactions

MECHANISM OF THE WILLIAMSON ETHER SYNTHESIS

The alkoxide functions as the nucleophile and attacks the electrophilic C of the alkyl halide displacing the bromide and creating the new C-O bond. This is an example of an SN2 reaction.
Williamson ether synthesis : a simple S<sub>N</sub>2 reaction

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary