1. 16.5 Properties of Esters
Ethyl acetate is the solvent in fingernail polish, plastics, and lacquers. Learning Goal Describe the boiling points and solubility of esters; draw the condensed structural formulas for the hydrolysis products.

2. Boiling Points of Esters
Esters have
boiling points higher than those of alkanes and ethers.
boiling points lower than those of alcohols and carboxylic acids of similar mass.
Because ester molecules do not have hydroxyl groups, they cannot hydrogen bond to each other.

3. Solubility of Esters in Water
Esters are soluble if they have two to five carbon atoms. As the number of carbons increases from five, their solubility in water decreases.
The partially negative oxygen of the carbonyl group forms hydrogen bonds with the partially positive hydrogen atoms of water molecules.

4. Acid Hydrolysis of Esters
In acid hydrolysis,
an ester reacts with water to produce a carboxylic acid and an alcohol.
a water molecule provides an —OH group to convert the carbonyl group of the ester to a carboxyl group.
an acid catalyst and heat are required.

5. Acid Hydrolysis of Esters
Aspirin that has been stored for a long time may undergo hydrolysis in the presence of water and heat.

6. Base Hydrolysis (Saponification)
Base hydrolysis, or saponification,
is the reaction of an ester with a strong base in the presence of heat.
produces a carboxylate salt and an alcohol.

7. Solution
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. Write equation for reaction of ethyl acetate and NaOH, in sample problem 16.8
ANALYZE Given Need
THE ester, base carboxylate salt
PROBLEM and alcohol

8. Study Check
Write the balanced chemical equation when methyl acetate reacts with A. water, heat, and an acid catalyst. B. KOH and heat.

9. Solution
Write the balanced chemical equation when methyl acetate reacts with A. water, heat, and an acid catalyst. B. KOH and heat.

10. Concept Map