Return to Contents Chapter 16: Ethers, Epoxides and Sulfides Ch 16 contents

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.
    Williamson ether synthesis : a simple S<sub>N</sub>2 reaction

    previous page
    next page
    © Dr. Ian Hunt, Department of Chemistry, University of Calgary