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Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
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
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
Naming Esters
Esters are named with the alkyl group of the alcohol, and the salt (-ate) of the carboxylic acid
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
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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.
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+ HOCH2CH3
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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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