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Problem 1c
Identify the following molecules as a carboxylic acid, an amide, an ester, or none of these.
c. CH₃COOH
Problem 3
Write both the complete structural formula of succinic acid (refer to Table 17.1), showing all bonds, and the line-angle structural formula.
Problem 8a
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).
Problem 9c
What are the names of the following compounds?
c. <IMAGE>
Problem 13a
Identify the following molecules as an ester, a carboxylic acid, or an amide, and write both the condensed and line-structural formula for each.
a. <IMAGE>
Problem 14b
Write the products of the following reactions:
b. 2, 2-Dimethylpentanoic acid + KOH → ?
Problem 15
Write the formulas of potassium salicylate and disodium oxalate (refer to Table 17.1).
Problem 17.28a
Identify the functional group in the following compounds and give the structures of the products of hydrolysis for these compounds.
a. <IMAGE>
Problem 17.34a
Consider the following unnatural amino acid: <IMAGE>
a. If two molecules react to form an ester, what is the structure of the ester product?
Problem 17.34c
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).
Problem 17.56
Draw structures of the carboxylic acids and alcohols you would use to prepare each ester in Problem 17.54.
Problem 17.67b
Household soap is a mixture of the sodium or potassium salts of long-chain carboxylic acids that arise from saponification of animal fat.
b. Draw the structures of the soap molecules produced in the following reaction: <IMAGE>
Problem 17.80
Write the formula of the triester formed from glycerol and stearic acid (Table 17.1).
Problem 17.82a
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
Problem 19.2
Based on the structure shown for retinol (vitamin A) and the names of the two related forms of vitamin A, retinal and retinoic acid, what do you expect to be the structural differences among these three compounds?
Problem 20a
Draw structures of the amides that can be made from the following reactants:
a. CH₃NH₂ + (CH₃)₂CHCOOH →?
Problem 20b
Draw structures of the amides that can be made from the following reactants:
b. <IMAGE>
Problem 21
Phenacetin (shown in the margin) was once used in headache remedies but is now banned because of its potential for causing kidney damage. (a) Identify all the functional groups present in phenacetin. (b) Draw the structures of the carboxylic acid and amine needed to prepare phenacetin. <IMAGE>
Problem 21.24
The reaction that follows is catalyzed by isocitrate dehydrogenase and occurs in two steps, the first of which (step A) is formation of an unstable intermediates (shown in brackets).
<IMAGE>
c. Which of the structures shown can be described as a ß-keto acid?
Problem 23a
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
a. Isopropyl benzoate
Problem 23b
Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.
b. <IMAGE>
Problem 24a
What carboxylic acids and amines result from hydrolysis of the following amides?
a. <IMAGE>
Problem 24b
What carboxylic acids and amines result from hydrolysis of the following amides?
b. N,N-Dimethyl-p-nitrobenzamide
Problem 26a
Give the structure of the repeating units in the polymers that are formed in the reactions of the following compounds.
a. <IMAGE>
Problem 31b
N-Acetylglucosamine (also known as NAG) is an important component on the surfaces of cells.
b. Draw the structures of the products of acid hydrolysis.
Problem 38
Write the equation for the ionization of hexanoic acid in water at pH 7.4. (Hint: See Section 17.2.)
Problem 39b
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.
Problem 39c
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.
Problem 42d
Give systematic names for the following carboxylic acids:
d. <IMAGE>
Problem 43d
Give systematic names for the following carboxylic acids:
d. CH₃(CH₂)₅COOH
