In experiment 6 we will perform a Fischer Esterification (Vollhardt, chapter 9-4 and 19-9). Suggest what could happen if you were to attempt recrystallization of a carboxylic acid with ethanol or an ester with water.

Fischer Esterification is a reversible reaction and the Le Châteliers principle can be used for the reaction to be completed. For the reverse reaction of Fischer Esterification, using the hydrolysis of ethyl ethanoate, the steps involved are:

1) An hydrogen ion is added to the ester and one of the lone pairs on the oxygen double-bonded to the carbon atom takes the hydrogen ion.

2) The lone pairs on the oxygen of a water molecule takes the positive charge on the carbon atom.

3) The hydrogen ion is transferred from one oxygen atom to another.

4) Then an ethanol molecule is released (one of the products).

5) Reaction with a water molecule releases hydrogen from the oxygen and the other product (ethanoic acid) is formed.