?The reaction of an organic acid with an alcohol, in organic solvent, to produce an

Chapter 15, Problem 15.60

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The reaction of an organic acid with an alcohol, in organic solvent, to produce an ester and water is commonly done in the pharmaceutical industry. This reaction is catalyzed by strong acid (usually \(\mathrm{H}_{2} \mathrm{SO}_{4}\) ). A simple example is the reaction of acetic acid with ethyl alcohol to produce ethyl acetate and water:

\(\mathrm{CH}_{3} \mathrm{COOH}(\text { solv })+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}(\text { solv }) \rightleftharpoons\)

\(\mathrm{CH}_{3} \mathrm{COOCH}_{2} \mathrm{CH}_{3}(\text { solv })+\mathrm{H}_{2} \mathrm{O}(\text { solv })\)

where "(solv)" indicates that all reactants and products are in solution but not an aqueous solution. The equilibrium constant for this reaction at \(55^{\circ} \mathrm{C}\) is 6.68. A pharmaceutical chemist makes up 15.0 L of a solution that is initially 0.275 M in acetic acid and 3.85 M in ethanol. At equilibrium, how many grams of ethyl acetate are formed?

Text Transcription:

H_2 SO_4

CH_3 COOH(solv)+CH_3 CH_2 OH (solv) rightleftharpoons

CH_3 COOCH_2 CH_3(solv)+H_2 O(solv)

55^circ C