16. Carboxylic Acids and Their Derivatives

Aspirin also known as acetylsalicylic acid possesses an ester group that is formed from the reaction between ethanoic acid and salicylic acid. Determine the structure of aspirin after the condensation between ethanoic acid and salicylic acid. 

Consider the following unnatural amino acid: <IMAGE>

a. If two molecules react to form an ester, what is the structure of the ester product?

Consider the following unnatural amino acid: <IMAGE>

c. Draw the cyclic ester resulting from the intramolecular reaction of the hydroxyl group of this amino acid with its carboxyl group (cyclic esters are called lactones).

Draw structures of the carboxylic acids and alcohols you would use to prepare each ester in Problem 17.54.

Each of the following materials has an ester that is responsible for its smell and/or flavor. Search the internet and determine what that ester is, draw its structure, and what carboxylic acid and alcohol are used to form it. 

a. Juicy Fruit gum flavoring

Write the formula of the triester formed from glycerol and stearic acid (Table 17.1).

Give the structure of the repeating units in the polymers that are formed in the reactions of the following compounds.

a. <IMAGE>

Write both condensed and line structures for (a) the ester formed when butyric acid reacts with cyclopentanol, (b) the amide formed when isopropyl amine is reacted with butyric acid, and (c) the amide formed when diethylamine is reacted with butyric acid. (d) Name the derivatives you created in parts (a)–(c).

Draw the condensed structural formula for the ester formed when each of the following reacts with methyl alcohol: 

b. pentanoic acid

Draw the condensed structural formula for the ester formed when each of the following reacts with ethyl alcohol: 

b. propionic acid

Draw the condensed structural or line-angle formula for the ester formed in each of the following reactions:                                                                                            

b. <IMAGE>

Draw the condensed structural or line-angle formula for the ester formed in each of the following reactions:

b. <IMAGE>

Methyl benzoate, which smells like pineapple guava, is used to train detection dogs. (14.3, 14.4)

b. Write the IUPAC name for the carboxylic acid and alcohol used to prepare methyl benzoate.

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

c. <IMAGE>  

Propyl acetate is the ester that gives the odor and smell of pears. (9.4, 10.6, 14.3, 14.4)

b. Write the balanced chemical equation for the formation of propyl acetate.