Question

Organic chemistry lab performing small scale Fisher esterification to make a variety of esters.

1) If you were doing these experiments on a larger scale, describe two ways that you could improve the yield of the target ester.

2) What is the point of adding sulfuric acid to the reaction? How about the heat?

3) Write the mechanism for the formation of wintergreen with 0.20g of anthranilic acid, 6 drops of methanol and one drop of H2SO4, then heated for three minutes followed by 15 drops of water.

Answer 1

1)

The Fischer Esterification reaction is formation of esters from carboxylic acids by reaction with the alcohols in presence of acidic catalyst. The reaction is always an equilibrium with the reactants & the products. The equilibrium can be shifted by the use of Le Chatelier's Principle

-one way is to remove one product from the reaction like the removal of the water molecule by use of azeotropic distillation or by the use of molecular sieves.

-The second way is to use the excess of one of the reactants like use of excess of the alochol or use alchol as the reaction medium.

2)

Sulfuric acid is a catalyst for the reaction; it allows the reaction to acheive the equilibrium. The heat is required to achieve the required activation energy of the reaction.

3)