Esters Presentation Final

Objectives
1.Describe the structure of esters. 2. Write the chemical equation for the preparation of esters. 3.Draw and name esters using IUPAC and common names. 4. Determine the properties and reactions of esters. 5.Describe the cleansing action on soap and detergent.
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition
Copyright 2012 by Pearson Education, Inc.
Esters
What are they?

3
In an ester, The H in the carboxyl group is replaced with an alkyl group
Esters are found in fats and oils responsible for the aroma and flavor of bananas, oranges, and strawberries
O CH3 COCH3 ester group
How are they made?

Formed when an alcohol reacts with a carboxylic
acid. Very slow reaction, unless! an acid catalyst used (usually sulphuric acid) A condensation reaction The condensation reaction between the hydroxyl group and the carboxylic acid known as esterification. Reverse reaction = ester hydrolysis
Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright 2012 by Pearson Education, Inc.
O + H
H O C O R
O C R O R
+
H2 O
This is why it is a condensation reaction because water is produced!
Definition of a condensation reaction = two molecules reacting to form a larger molecule with the elimination of a small molecule such as water
FORWARD REACTION = condensation reaction, the esterification of an alcohol using acid catalyst under reflux. R O + H H O C O R
O C R O + H2 O R
REVERSE REACTION = ester hydrolysis, same catalyst works for both forward & reverse reactions.
Esterification
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Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester.
Esterification
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An example of esterification is the reaction of a ethanoic acid with 1-propanol to produce an ester called propylethanoate, responsible for the smell of pears.
Learning Check
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Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst.
Solution
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Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. O CH3CH2COH + HOCH3 Propanoic acid Methanol H+
O CH3CH2COCH3 + H2O
Naming
Names of esters end in oate.
Named after alcohol & carboxylic acid from which they are derived. O lets name some esters! C CH3
CH3 CH2 ethyl this part comes from the alcohol & is named after it O ethanoate this part from the acid and is named after it
Structural formulae
Although the previous structural formula are the clearest way of showing esters, they can draw out in a shortened form. In this version ethyl ethanoate O Either CH3 CH2 O C CH3 Or
the acid part has been written first
CH3 C
CH2
CH3
Identify the group attached to the C=O this is

from the acid The group attached to the O- is from the alcohol.
Naming Esters
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Esters have IUPAC and common names:
Guide to Naming Esters

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What is the IUPAC name and common name of the following ester? O || CH3CH2CH2COCH2CH3

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What is the IUPAC name of the following ester? Step 1 Write the name of the carbon chain from the alcohol as an alkyl group.
O || CH3CH2CH2COCH2CH3 ethyl

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What is the IUPAC name of the following ester? Step 2 Change the -ic acid of the acid name to -ate. O || CH3CH2CH2COCH2CH3 ethyl butanoate
Learning Check
18
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O CH3 COCH2CH2CH3
Solution
19
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. Step 1 Write the name of the carbon chain from the alcohol as an alkyl group. O CH3COCH2CH2CH3 propyl
Solution
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Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. Step 2 Change the -ic acid of the acid name to -ate. O CH3COCH2CH2CH3 propyl ethanoate (IUPAC) propyl acetate (common)
Learning Check
Write the structure of the following esters:
A. Ethyl pentanoate
B. Propyl butyrate
21
Solution
A. Ethyl pentanoate O CH3CH2CH2CH2COCH2CH3 B. Propyl butyrate O CH3CH2CH2COCH2CH2CH3
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Learning Check
Name the following esters: O A. CH3CH2CH2COCH3
O B. CH3CH2 COCH2CH3
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24
Pictionary Game
25
Pictionary rules: Split class into two teams. Draw line up middle of board. Each team selects a volunteer to come to front. The volunteers from each team select one yellow card and one red card. They must then draw the structure of the ester formed from the reaction of the acid and the alcohol. First to do so wins. For extra points, students in teams must name the ester drawn and the acid and alcohol it is made from
Ester Products
26
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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Esters in Fruits
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Esters give pleasant fragrances and flavors to many fruits and flowers.
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Wait! Whats that smell?

Properties/Reactions of Esters
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
30
Acid Hydrolysis of Esters

31
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 carboxylic acid alcohol formic acid ethanol
Base Hydrolysis (Saponification)

32
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 sodium acetate ethanol
Soaps
The base hydrolysis of long chain fatty acids produces acid salts called soaps.
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Cleaning Action of Soap

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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
Cleaning Action of Soap

35
Simplified Action of Soap
37
Cleansing Action Of Soap and Detergent
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42
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Learning Check
45
Write the organic products when methyl acetate reacts with A. water and an acid catalyst
B. KOH
Solution
46
Write the organic products when methyl acetate reacts with A. water and an acid catalyst O H+ CH3COCH3 CH3COH + HOCH3 B. KOH O O Heat CH3COCH3 CH3COK+ + HOCH3

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Objectives

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

What are they?

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

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

How are they made?

This is why it is a condensation reaction because water is produced!

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Names of esters end in oate.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

the acid part has been written first

Identify the group attached to the C=O this is

Copyright 2012 by Pearson Education, Inc.

Esters have IUPAC and common names:

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Guide to Naming Esters

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Guide to Naming Esters

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Guide to Naming Esters

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Wait! Whats that smell?

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

Acid Hydrolysis of Esters

Base Hydrolysis (Saponification)

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Cleaning Action of Soap

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Copyright 2012 by Pearson Education, Inc.

Cleaning Action of Soap