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

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 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.

Ethyne (HC≡CH) has a pK_a value of 25, water has a pK_a value of 15.7, and ammonia (NH₃) has a pK_a value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with

b. ⁻NH₂.

c. Which would be a better base to use if you wanted to remove a proton from ethyne, HO⁻ or ^-NH₂?

For each of the acid–base reactions in [Section 2.3], compare the pK_a values of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated.

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For each of the acid–base reactions in [Section 2.3], compare the pK_a values of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated.

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Ethyne (HC≡CH) has a pK_a value of 25, water has a pK_a value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with

a. HO^-.