Chapter 13 Carboxylic Acids, Esters, Amines, and Amides

13.3 Esters

Esters
In an ester, the H in the carboxyl group is replaced with an alkyl group. O CH3 COCH3 ester group

Esterification
Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. O H+ CH3COH + HOCH2CH3 O CH3COCH2CH3 + H2O Ethyl acetate (an ester)
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Learning Check
Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst.

Solution
Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. O H+ CH3CH2COH + HOCH3 Propanoic acid Methanol O CH3CH2COCH3 + H2O

Ester Products
Aspirin is used to relieve pain and reduce inflammation. is an ester of salicylic acid and acetic acid. Oil of wintergreen is used to soothe sore muscles. is an ester of salicylic acid and methanol.

O C OH O O C CH3

O C O CH3 OH

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Naming Esters
The name of an ester contains the names of the alkyl group from the alcohol. the carbon chain from the acid with ate ending. methyl ethanoate (acetate) O CH3 OC CH3

IUPAC: methyl ethanoate common: methyl acetate

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Naming Esters
Esters are named with the alkyl group of the alcohol, and the salt (-ate) of the carboxylic acid

From ethanoic acid (acetic acid)

From methanol (methyl alcohol)

Esters in Plants
Esters give pleasant fragrances and flavors to many fruits and flowers.

Learning Check
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O CH3 COCH2CH2CH3

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Solution
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears.
from 1-propanol

O CH3COCH2CH2CH3 propyl ethanoate (IUPAC) propyl acetate (common)

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Learning Check
Draw the structure of the following compounds. A. 3-bomobutanoic acid

B. Ethyl propionoate

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Solution
A. 3-bromobutanoic acid Br | CH3CHCH2COOH

B.

Ethyl propionoate O CH3CH2 COCH2CH3

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Acid Hydrolysis of Esters

In acid hydrolysis an ester reacts with water to produce a carboxylic acid and an alcohol. an acid catalyst is required. O H+ HCOCH2CH3 + H2O O HCOH

+ HOCH2CH3

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Base Hydrolysis (Saponification)

Base hydrolysis or saponification, is the reaction of an ester with a strong base. produces the salt of the carboxylic acid and an alcohol. O || CH3COCH2CH3 + NaOH O CH3CO Na+ + HOCH2CH3
salt of carboxylic acid alcohol

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Base Hydrolysis of Fatty Acids Produces Soaps

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Cleaning Action of Soap

A soap contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end that dissolves in water. forms groups of soap molecules called micelles that dissolve in water and are washed away.
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Learning Check
Write the organic products when methyl acetate reacts with A. water and an acid catalyst.

B. KOH.

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Solution
Write the organic products when methyl acetate reacts with A. water and an acid catalyst. O CH3COH + HOCH3 B. KOH. O CH3CO K+ + HOCH3

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