Esterifi cation is the reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) to

Chapter 6, Problem 6.57

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Esterifi cation 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 esterifi cation reaction. Equation [2] is an example of an intramolecular esterifi cation reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as product. The equilibrium constants for both reactions are given. Explain why Keq is different for these two apparently similar reactions. + CH3CH2OH H2O OH OH O O O + + H2O [1] [2] Keq = 4 Keq 1000 ethyl acetate = CH3 C OH O C O CH3 OCH2CH3

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