Williamson ether synthesis is conducted using vanillin, $\ce{KOH}$, $\ce{EtOH}$, water and benzyl chloride.

  1. Why is water needed for the synthesis?
  2. Why must the solution be refluxed for an hour to gain the desired product?
  3. Why is water added after reflux to create a cloudy solution?


  • Consider the phases for potassium hydroxide and benzyl chloride at room temperature.
  • Why might you not want to use ethanol as the solvent to form the benzyl alkoxide of vanillin in?
  • (As an aside, think about why you might not want to use water over, say, acetonitrile as a solvent for this reaction.)


  • What governs the rate of the Williamson ether synthesis?

  • Why would you want to heat a chemical system you want to have a reaction in?


  • What solvents would the product ether dissolve in?

  • Which by-product(s) would dissolve in water but not ethanol?

  • How would you remove the product ether from the solvent mixture?

I'm trying not to give away the answers directly but these bullet points should help you work out each point.


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