Chapter 16 Carboxylic Acids and

Esters
16.3 Esters
16.4 Naming Esters

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Esters
In an ester,
 the H in the carboxyl group is replaced
with an alkyl group

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Esterification
Esterification is
 the reaction of a carboxylic acid and alcohol in the
presence of an acid catalyst to produce an ester

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Guide to Naming Esters

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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

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Learning Check
Write the equation for the reaction of propanoic acid
and methanol in the presence of an acid catalyst.

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Solution
Write the equation for the reaction of propanoic acid
and methanol in the presence of an acid catalyst.

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Learning Check
Give the IUPAC and common names of the following
compound, which is responsible for the flavor and odor
of pears:

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Solution
from 1-propanol

STEP 1 Write the carbon chain from the alcohol as alkyl.

Propyl
STEP 2 Change ic acid to ate.
Ethanoate (acetate)
Propyl ethanoate (IUPAC name)
Propyl acetate (common name)
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Learning Check
Name the following esters:

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Solution
A. STEP 1 Write the carbon chain from the alcohol as
alkyl. Methyl
STEP 2 Change butanoic acid (butyric acid) to
butanoate (butyrate).
Methyl butanoate (methyl
butyrate)
B. STEP 1 Write the carbon chain from the alcohol as
alkyl. Ethyl
STEP 2 Change propanoic acid (propionic acid) to
propanoate (propionate)
Ethyl propanoate (ethyl
propionate)
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Learning Check
Draw the condensed structural formula of the following
esters:

A. Ethyl pentanoate

B. Propyl butyrate

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Solution
Draw the condensed structural formula of the following
esters:

A. Ethyl pentanoate

B. Propyl butyrate

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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
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Esters in Plants

Esters give flowers

and fruits their
pleasant fragrances
and flavors.

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