Fischer Esterification Reversible?

Question

Can anyone tell me why the Fischer Esterification reaction is reversible? This confuses me.

Answer 1

The Lewis or Brønstedt acid-catalyzed esterification of carboxylic acids with alcohols to give esters is a typical reaction in which the products and reactants are in equilibrium.

The equilibrium may be influenced by either removing one product from the reaction mixture (for example, removal of the water by azeotropic distillation or absorption by molecular sieves) or by employing an excess of one reactant.

If you want to reverse the equilibrium, add water or remove the alcohol.

Answer 2

Carboxylic Acid + Alcohol (excess) + HCl (catalytic) -----> Ester + H20

this reaction goes forward because of the excess amount of alcohol.

reversing this is just a matter of shifting the equilibrium constant to K>1

this is done either by adding excess H2O or removing your alcohol (usually both)

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in other words, you can reverse it by purifying the ester and running the reaction in excess water.

Ester + H20 (excess) + HCl -------> Carboxylic Acid + Alcohol

Answer 3

think about it this way if it takes acid to get the reaction to go then if you add base you have a good chance of reversing it