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#SEPHI

ESTERS

By :

1
Esters, who are they?
Esters are a derivative from acids, prepared by the
reaction of carboxylic acid and an alcohol.
In an ester,
The H in the carboxyl group is replaced
with an alkyl group.

O

CH3 COCH3
ester group
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings

2
Nomenclature of esters
The name of an ester contains the names of
The alkyl group from the alcohol. (FIRST!)
The carbon chain from the acid with ate ending. (SECOND!)
from alcohol from acid
O
methyl
CH3 OC CH3
ethanoate (acetate)
IUPAC : methyl ethanoate
Common : methyl acetate
CONTINUE... 3
Names of esters
end in oate.

O
C CH3
CH3 CH2 O
ethyl ethanoate

this part comes from this part from the


the alcohol & is named acid and is named
after it after it

Identify the group attached to the C=O this is from the


acid
The group attached to the O- is from the alcohol. 4
Formate Methanoate
Acetate Ethanoate
Examples Propionate Propanoate
Butyrate Butanoate

Raspberries
HCOOCH2CH3 ethyl methanoate (IUPAC)
ethyl formate (common)

Pineapples
CH3CH2CH2 COOCH2CH3
ethyl butanoate (IUPAC)
ethyl butyrate (common)

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Learning Check-1

Name the following esters:


O

A. CH3CH2CH2COCH3

O

B. CH3CH2 COCH2CH3

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Solution

Name the following esters:


O

A. CH3CH2CH2COCH3 Methyl butyrate

O

B. CH3CH2 COCH2CH3 Ethyl propanoate

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Learning Check-2

Draw the structure of the following esters:

A. Ethyl pentanoate

B. Propyl butanoate

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Solution

A. Ethyl pentanoate
O

CH3CH2CH2CH2COCH2CH3

B. Propyl butanoate
O

CH3CH2CH2COCH2CH2CH3

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Learning Check-3

Give the IUPAC and common names of the following


compound, which is responsible for the flavor and odor
of pears.

O

CH3 CO CH2CH2CH3

10
Solution

O
propyl
CH3 CO CH2CH2CH3

propyl ethanoate (IUPAC)


propyl acetate (common)

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Learning Check-4

Draw the structure of the following compounds:

A. 3-bromobutanoic acid

B. Ethyl propanoate

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Solution

A. 3-bromobutanoic acid
Br
|
CH3CHCH2COOH

B. Ethyl propionoate
O

CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3
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Physical properties of
esters
1. Boiling Point
Esters, like aldehydes and ketones, are polar. However,
they do not form ester-ester hydrogen bonds, so their
boiling points are significantly lower than those of an
acid with the same number of carbon atoms.

Molecule Type Boiling Point (C)

CH3COOCH2CH3 ester 77.1

CH3CH2CH2COOH carboxylic acid 164

CONTINUE...
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Physical properties of
esters
2. Solubility in Water
Small esters are fairly soluble in water but solubility
decreases with increasing chain length, as shown
below:

ester formula solubility (g per 100 g


of water)

ethyl methanoate HCOOCH2CH3 10.5

ethyl ethanoate CH3COOCH2CH3 8.7

ethyl propanoate CH3CH2COOCH2CH3 1.7

CONTINUE...
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Physical properties of
esters
2. Solubility in Water
The reason for this trend in solubility is that although
esters cannot hydrogen bond with each other, they can
hydrogen bond with water molecules. One of the
partially-positive hydrogen atoms in a water molecule
can be sufficiently attracted to one of the lone pairs on
one of the oxygen atoms in an ester, forming a
hydrogen bond.

CONTINUE...
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Physical properties of
esters
Esters are colourless and exist in liquid state at room
temperature.
Esters are volatile in nature, more then carboxylic
acids.
Small chained esters are colorless liquid with
pleasant odor, esters with higher molar mass are
odorless.
Many have pleasant aromas,
o Isoamyl acetate = banana oil
o 3-methylbutyl ethanoate
o Ethyl butanoate = pineapple aroma
o Ethyl butanoate
o Isobutyl formate = raspberry aroma
o Isobutyl methanoate
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chemical properties of
esters
1. 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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chemical properties of
esters
Hydrolysis is the opposite of esterification

ESTER + WATER CARBOXYLIC ACID + ALCOHOL

The products of hydrolysis depend on the conditions used...

acidic CH3COOCH3 + H2O CH3COOH + CH3OH

alkaline CH3COOCH3 + NaOH > CH3COO Na+ + CH3OH

If the hydrolysis takes place under alkaline conditions,


the organic product is a water soluble ionic salt

The carboxylic acid can be made by treating the salt with HCl
CH3COO Na+ + HCl > CH3COOH + NaCl
chemical properties of
esters
2. Saponification of Esters (Base Hydrolysis)
Is the reaction of an ester with a strong bases such
as NaOH and KOH.
Produces the salt of the carboxylic acid and an
alcohol.
O
|| heat
CH3COCH2CH3 + NaOH
O

CH3CO Na+ + HOCH2CH3
salt of carboxylic acid alcohol
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chemical properties of
esters
It can be reduced by strong reducing agents such as
LiAlH4 or NaBH4 to produce alcohol

R-COOH R-CH2-OH

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PREPARATION OF ESTERS 1
(FROM CARBOXYLIC ACID AND ALCOHOLS)

Reagent(s) alcohol + carboxylic acid

Conditions reflux with a strong acid catalyst (e.g. conc. H2SO4 )

Equation e.g. CH3CH2OH(l) + CH3COOH(l) CH3COOC2H5(l) + H2O(l)


ethanol ethanoic acid ethyl ethanoate

Notes Conc. H2SO4 is a dehydrating agent - it removes water


causing the equilibrium to move to the right and thus
increases the yield of the ester

CONTINUE...
PREPARATION OF ESTERS 2
(FROM ACYL CHLORIDE AND ALCOHOL)

Reagent(s) alcohol + acyl chloride

Conditions reflux under dry conditons

Equation e.g. CH3OH(l) + CH3COCl(l) > CH3COOCH3(l) + HCl(g)


methanol ethanoyl methyl
chloride ethanoate

Notes Acyl chlorides are very reactive


but must be kept dry as they react
with water.

CONTINUE...
PREPARATION OF ESTERS 3
(FROM ACID ANHYDRIDE AND ALCOHOL)

Reagent(s) alcohol + acid anhydride

Conditions reflux under dry conditons

Equation e.g. CH3OH(l) + (CH3CO)2O(l) > CH3COOCH3(l) + CH3COOH(l)


methanol ethanoic methyl ethanoic
anhydride ethanoate acid

Notes Acid anhydrides are not as reactive as


acyl chlorides so the the reaction is slower.

The reaction is safer - it is less exothermic.

Acid anhydrides are less toxic.


STRUCTURAL ISOMERISM
FUNCTIONAL GROUP

Classification CARBOXYLIC ACID ESTER

Functional Group R-COOH R-COOR

Name PROPANOIC ACID METHYL ETHANOATE

Physical properties O-H bond gives rise No hydrogen bonding


to hydrogen bonding; insoluble in water
get higher boiling point
and solubility in water

Chemical properties acidic fairly unreactive


react with alcohols hydrolysed to acids
USES OF ESTERS

Esters in Synthetic Lubricants


The Hatco Corporation
Esters have been used successfully in lubrication
for more than 50 years. For example, esters have
been used exclusively in jet engine lubricants
worldwide due to their unique combination of
low temperature ease of flow with clean high
temperature operation.

CONTINUE...
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USES OF ESTERS

Artificial fruit flavours in foods


Esters have been use in all food products
containing artificial flavouring for years. They
create distinct flavours and aromas which is
what often sells the product. Flavours: Orange
octyl ethanoate, grape- ethly heptanoate,
banana- 3-methlybutyl ethanoate, and etc.
Also used as fruity flavours for foods and drinks
such as milkshakes, ice-cream, chewing gum,
jellies, sweets and cakes.

CONTINUE...
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An industrial use of esters include the production of oils, such as bio diesel.
Bio diesel is made using fatty acids (a carboxylic acid) taken from the seeds of
plants and methanol (an alcohol). Heat and a concentrated acid is then used
to quicken the reaction process. Linolenic acid and methanol are used to
create bio diesel. Linolenic acid is found in vegetable or animal fats. As well as
bio diesel being produce, small amounts of glycerine are also produced.

CONTINUE...
Soaps
The base hydrolysis of long chain fatty acids
produces acid salts called soaps.

CONTINUE...
29
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
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.

Copyright 2007 by Pearson Education, Inc. 30


Publishing as Benjamin Cummings
Ester Products
Aspirin O
Is used to relieve pain and C OH
reduce inflammation. O
Is an ester of salicylic acid
O C CH3
and acetic acid.

Oil of wintergreen
O
Is used to soothe sore
muscles. C O CH3
Is an ester of salicylic acid
and methanol. OH

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Esters in Plants
TABLE 16.4
Esters give
flowers and
fruits their
pleasant
fragrances and
flavors.

32
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Learning Check

Write the organic products when methyl acetate reacts


with
A. Water and an acid catalyst

B. KOH

33
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

34
Learning Check

Give the IUPAC and common names of the following


compound, which is responsible for the flavor and odor
of pears.

O

CH3COCH2CH2CH3

35
Learning Check

Give the IUPAC and common names of the following


compound, which is responsible for the flavor and odor
of pears.

O

Propyl acetate / Propyl
CH3COCH2CH2CH3 ethanoate

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