(57) Esterification is the reaction of a carboxylic acid (RCOOH) with an alcohol

Question

(57) Esterification is the reaction of a carboxylic acid (RCOOH) with an alcohol (R,OH) to form an ester (RCOOR') with loss of water. Equation [1] is an example of an intermolecular esterification reaction. Equation [2] is an example of an intramolecular esterification reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as a product. The equilibrium constant for both reactions are given. Explain why Keq is different for these two apparently similar reactions · OH ethyl acetate OH 12] H2O Keq-1000 OH

Explanation / Answer

In reaction 1, two molecule of reactants produce two molecules of products while in reaction 2, one molecule of reactant produces two molecules of product. So, the in reaction 2 entropy of the system increase as the reaction proceeds that make it more spontaneous than reaction 1. Thus at equilibrium concentration of product is very high compared to reactant and giving rise to a very high value of Keq.

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