How would you make ethyl ethanoate?

1 Answer
Truong-Son N.
Jan 19, 2016

One starting point is acetylene.

  1. A simple acid-catalyzed hydration (one of the first reactions you should have learned), except it is updated by adding mercury sulfate to accommodate for the decreased reactivity of alkynes to hydration reactions in comparison to alkenes.
  2. A keto-enol tautomerization in acid, of the enol into an aldehyde. The aldehyde is favored.
  3. Oxidation to a carboxylic acid via chromic acid (something from second semester).
  4. Esterification of the carboxylic acid (obviously into an ester) by reacting with a large excess of ethanol in acidic conditions.
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