Identify the following molecules as a carboxylic acid, an amide, an ester, or none of these.

c. CH₃COOH

Write both the complete structural formula of succinic acid, showing all bonds, and the line-angle structural formula.

In the following pairs of compounds, which would you expect to be more soluble in water? Why?

a. C₈H₁₇COOH or CH₃CH₂CH₂COOH

Write both condensed and line structures for (a) the ester formed when butyric acid reacts with cyclopentanol.

What are the names of the following compounds?

c.

Identify the following molecules as an ester, a carboxylic acid, or an amide, and write both the condensed and line-structural formula for each.

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Write the products of the following reactions:

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

Write the formulas of potassium salicylate and disodium oxalate.

Draw structures of the amides that can be made from the following reactants:

a. CH₃NH₂ + (CH₃)₂CHCOOH →?

Draw structures of the amides that can be made from the following reactants:

b.

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.

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.

a. Isopropyl benzoate

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.

b.

What carboxylic acids and amines result from hydrolysis of the following amides?

a.

What carboxylic acids and amines result from hydrolysis of the following amides?

b. N,N-Dimethyl-p-nitrobenzamide

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

a.

Write the formula for the phosphate monoester formed from isopropyl alcohol and phosphoric acid.

Identify the functional group in the following compounds and give the structures of the products of hydrolysis for these compounds.

a.

Identify the functional group in the following compounds and give the structures of the products of hydrolysis for these compounds.

b. CH₃CH₂OPO₃^2-

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.

One phosphorylated form of glycerate is 3-phosphoglycerate

a. Identify the type of linkage between glycerate and phosphate.

Consider the following unnatural amino acid:

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

Consider the following unnatural amino acid:

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 the structures of the following compounds and use dashed lines to indicate where they form hydrogen bonds to other molecules of the same kind: (ii) methyl formate

Draw the structures of the following compounds and use dashed lines to indicate where they form hydrogen bonds to other molecules of the same kind: (i) formic acid

Arrange these compounds in order of increasing boiling points and explain your rationale for the order.

(i) formic acid

(ii) methyl formate

(iii) formamide.

Write the equation for the ionization of hexanoic acid in water at pH 7.4.

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.

Give systematic names for the following carboxylic acids:

d.