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

Synthesis of Ethers via Acid-catalysed Condensation of Alcohols

ether synthesis by alcohol condensation

Reaction type: Nucleophilic Substitution (SN2)

Summary

QUESTIONS

 
  • Why can this reaction be termed a condensation reaction ?
  • ANSWER
     
  • Why is the reaction unsuitable for unsymmetrical ether synthesis ?
  • ANSWER

    Related reactions

    MECHANISM FOR  OF ALCOHOL CONDENSATION TO GIVE AN ETHER
    Step 1:
    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.
    acid-catalysed alcohol condensation mechanism
    Step 2:
    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.
    Step 3:
    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.


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