16. Carboxylic Acids and Their Derivatives

Name the carboxylate anion formed in the following reaction.

Write the products of the following reactions:

b. 2, 2-Dimethylpentanoic acid + KOH → ?

Write the equation for the ionization of hexanoic acid in water at pH 7.4. (Hint: See Section 17.2.)

Suppose you have a sample of benzoic acid dissolved in water.

b. Now assume that aqueous NaOH is added to the benzoic acid solution until pH 12 is reached. Draw the structure of the major organic species present.

Suppose you have a sample of benzoic acid dissolved in water.

c. Finally, assume that aqueous HCl is added to the solution from (b) until pH 2 is reached. Draw the structure of the major organic species present.

Procaine, a local anesthetic whose hydrochloride is Novocain, has the following structure. Identify the functional groups present, and show the structures of the alcohol and carboxylic acids you would use to prepare procaine. <IMAGE> Procaine

Lactones are cyclic esters in which the carboxylic acid part and the alcohol part are connected to form a ring. One of the most notorious lactones is gamma-butyrolactone (GBL), whose hydrolysis product is the 'date-rape' drug GHB. Draw the structure of GHB. <IMAGE> GBL

A simple polyamide can be made from ethylenediamine and oxalic acid (Table 17.1). Draw the polymer formed when three units of ethylenediamine reacts with two units of oxalic acid.

<IMAGE> Ehtylenediamine

Write the balanced chemical equation for the dissociation of each of the following carboxylic acids in water:

a. pentanoic acid

Write the balanced chemical equation for the dissociation of each of the following carboxylic acids in water:

b. butanoic acid

Identify the compound in each group that is most soluble in water. Explain.

b. pentane, 1-hexanol, propanoic acid

Identify the compound in each group that is most soluble in water. Explain.

b. ethanoic acid (acetic acid), hexanoic acid, octanoic acid

Draw the condensed structural or line-angle formulas for the products of the following: (14.2, 14.3, 14.6)

b. <IMAGE>

Write the balanced chemical equation for the reaction of each of the following carboxylic acids with NaOH:

c. benzoic acid

Write the balanced chemical equation for the reaction of each of the following carboxylic acids with KOH:

b. 2-methylbutanoic acid