Sample Problem 16.1 Naming Carboxylic Acids Give the IUPAC and common name for the following carboxylic acid: Solution Step 1 Identify the longest carbon chain and replace the e in the corresponding alkane name with oic acid. The IUPAC name of a carboxylic acid with four carbons is butanoic acid; the common name is butyric acid.

Sample Problem 16.1 Naming Carboxylic Acids Continued Step 2 Name and number any substituents by counting the carboxyl group as carbon 1. With a methyl group on the second carbon, the IUPAC name is 2-methylbutanoic acid. For the common name, the Greek letter α specifies the carbon atom next to the carboxyl carbon, α-methylbutyric acid. Study Check 16.1 Give the IUPAC and common name for the following: Answer 3-chlorobenzoic acid (m-chlorobenzoic acid)

Sample Problem 16.2 Boiling Points of Carboxylic Acids Match each of the compounds 2-butanol, pentane, propanoic acid with a boiling point of 141 °C, 100 °C, or 36 °C. (They have about the same molar mass.) Solution The boiling point increases when the molecules of a compound can form hydrogen bonds or have dipole–dipole attractions. Pentane has the lowest boiling point, 36 °C, because alkanes cannot form hydrogen bonds or dipole–dipole attractions. 2-Butanol has a higher boiling point, 100 °C, than pentane because an alcohol can form hydrogen bonds. Propanoic acid has the highest boiling point, 141 °C, because carboxylic acids can form stable dimers through hydrogen bonding to increase their effective molar mass and therefore their boiling points. Study Check 16.2 Why would methanoic acid (molar mass 46, bp 101 °C) have a higher boiling point than ethanol (molar mass 46, bp 78 °C)? Answer Two methanoic acid molecules form a dimer, which gives an effective molar mass that is double that of a single acid molecule. Thus, a higher boiling point is required than for ethanol.

Sample Problem 16.3 Dissociation of Carboxylic Acids in Water Write the balanced chemical equation for the dissociation of propanoic acid in water. Solution A chemical equation for the dissociation of a carboxylic acid includes the reactants, a carboxylic acid and water, and the products, carboxylate and hydronium ions. Study Check 16.3 Write the balanced chemical equation for the dissociation of formic acid in water. Answer

Sample Problem 16.4 Neutralization of Carboxylic Acid Write the balanced chemical equation for the neutralization of propanoic acid (propionic acid) with sodium hydroxide. Solution A chemical equation for the neutralization of carboxylic acid includes the reactants, a carboxylic acid and a base, and the products, a carboxylate salt and water. Study Check 16.4 What carboxylic acid will give potassium butanoate (potassium butyrate) when it is neutralized by KOH? Answer butanoic acid (butyric acid)

Sample Problem 16.5 Writing Esterification Equations An ester that has the smell of pineapple can be synthesized from butanoic acid and methanol. Write the balanced chemical equation for the formation of this ester. Solution In an esterification equation, a carboxylic acid and an alcohol react to form an ester and water. The ester product of the esterification of butanoic acid and methanol is methyl butanoate. Study Check 16.5 The ester that smells like plums can be synthesized from methanoic acid and 1-butanol. Write the balanced chemical equation for the formation of this ester.

Sample Problem 16.5 Writing Esterification Equations Continued Answer

Sample Problem 16.6 Naming Esters What are the IUPAC and common names of the following ester? Solution Step 1 Write the name for the carbon chain from the alcohol as an alkyl group. The alcohol part of the ester is from propanol (propyl alcohol). The alkyl group is propyl.

Sample Problem 16.6 Naming Esters Continued Step 2 Change the ic acid of the acid name to ate. The carboxylic acid part of the ester is from propanoic (propionic) acid, which becomes propanoate (propionate). The ester is named propyl propanoate (propyl propionate). Replacing the ic acid in the common name propionic acid with ate gives propionate. The common name for the ester is propyl propionate. Study Check 16.6 Draw the line-angle structural formula for ethyl heptanoate that gives odor and flavor to grapes. Answer

Sample Problem 16.7 Acid Hydrolysis of Esters Aspirin that has been stored for a long time may undergo hydrolysis in the presence of water and heat. What are the hydrolysis products of aspirin? Solution

Sample Problem 16.7 Acid Hydrolysis of Esters Continued To write the hydrolysis products, separate the compound at the ester bond. Complete the formula of the carboxylic acid by adding —OH (from water) to the carbonyl group and —H to complete the alcohol. The acetic acid in the products gives the odor of vinegar to a sample of aspirin that has hydrolyzed. Study Check 16.7 What are the names of the products from the acid hydrolysis of ethyl propanoate (ethyl propionate)? Answer propanoic acid and ethanol (propionic acid and ethyl alcohol)

Sample Problem 16.8 Base Hydrolysis of Esters Ethyl acetate is a solvent used in fingernail polish, plastics, and lacquers. Write the balanced chemical equation for the hydrolysis of ethyl acetate with NaOH. Solution

Sample Problem 16.8 Base Hydrolysis of Esters Continued Study Check 16.8 Draw the condensed structural formulas for the products from the hydrolysis of methyl benzoate with KOH. Answer