The acid-catalyzed hydrolysis of an ester results in the formation of an equal amount of carboxylic acid and alcohol.
(a) Design a flow chart for separating the two products.

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(d)

Would amide or acetate most easily deprotonate an alcohol to make the alkoxide anion? Calculate K_eq for each possibility.

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Complete the following proposed acid–base reactions, and predict whether the reactants or products are favored.

(a)

(b)

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline

Phenols are less acidic than carboxylic acids, with values of pK_a around 10. Phenols are deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.

For the following acid–base pairs, (iii) predict the favored side of equilibrium;

(e)