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Introduction:
What are esters?.
Ester are derived from carboxylic acids. A

carboxylic acid contains the -COOH group,
and in an ester the hydrogen in this group is
replaced by a hydrocarbon group of some
kind. This could be an alkyl group like methyl
or ethyl, or one containing a benzene ring like
.phenyl.
A common ester - ethyl ethanoate
The most commonly discussed ester is ethyl

ethanoate. In this case, the hydrogen in the -
COOH group has been replaced by an ethyl
group. The formula for ethyl ethanoate is:
Notice that the ester is named the opposite

way around from the way the formula is
-1-
written. The "ethanoate" bit comes from
ethnic acid. The "ethyl" bit comes from the
ethyl group on the end.
A few more esters
In each case, be sure that you can see how

the names and formulae relate to each other.
Notice that the acid is named by counting up

the total number of carbon atoms in the
chain - including the one in the -COOH group.
So, for example, CH3CH2COOH is propanoic
-2-
acid, and CH3CH2COO is the propionate
group.
Fats and oils

Differences between fats and oils
Animal and vegetable fats and oils are just big

complicated esters. The difference between a
fat (like butter) and an oil (like sunflower oil)
is simply in the melting points of the mixture
of esters they contain.
If the melting points are below room

temperature, it will be a liquid - an oil. If the
melting points are above room temperature,
it will be a solid - a fat.
-3-
The causes of the differences in melting
points will be discussed further down the
page under physical properties.
Fats and oils as big esters
Esters can be made from carboxylic acids and

alcohols. This is discussed in detail on another
page, but in general terms, the two combine
together losing a molecule of water in the
process.
We'll start with a very, very simple ester like
ethyl ethanoate - not something complicated
like a fat or oil!
The diagram shows the relationship between
the ethnic acid, the ethanol and the ester.
-4-
This isn't intended to be a full equation. Water, of course, is also
produced
Now let's make the alcohol a bit more complicated by having
more than one -OH group. The diagram below shows the
structure of propane-1,2,3-triol (old name: glycerol).
Just as with the ethanol in the previous equation, I've drawn this
back-to-front to make the next diagrams clearer. Normally, it is
drawn with the -OH groups on the right-hand side.
If you make an ester of this with ethanoic acid, you could attach
three ethanoate groups.
-5-
Now, make the acid chains much longer, and you finally have
a fat.
The Acid Ch3(Ch2)16COOH Is Called Octadecanoic Acid, But
The Old Name Is Still Commonly Used. This Is Stearic Acid.
The full name for the ester of this with propane-1,2,3-triol is
propane-1,2,3-triyl trioctadecanoate. But the truth is that almost
everybody calls it (not surprisingly!) by its old name of glyceryl
tristearate.
-6-
Physical properties:
Simple esters
I am thinking here about things like ethyl ethanoate.
Boiling points
The small esters have boiling points which are similar to those of
aldehydes and ketones with the same number of carbon atoms.
Like aldehydes and ketones, they are polar molecules and so have
dipole-dipole interactions as well as van deer Waals dispersion
forces. However, they don't form hydrogen bonds, and so their
boiling points aren't anything like as high as an acid with the same
number of carbon atoms.
For example:
Molecule Type Boiling point( °C)
CH3COOCH2CH3 ester 77.1
CH3CH2CH2COOH carboxylic acid 164
-7-
Solubility in water
The small esters are fairly soluble in water but solubility falls with
chain length.
For example:
formula solubility (g per 100

Ester
g of water
ethyl methanoate HCOOCH2CH3 10.5
The reason for the solubility is that although esters can't hydrogen
bond with themselves, they can hydrogen bond with water
molecules.
Chemical Properties:
1. Hydrolysis
We have already learnt that hydrolysis of esters gives alcohol and
carboxylic acid.
2. Reaction with alcohol ( Transesterification)
-8-
Esters of an alcohol can react with another alcohol in the presence of
a mineral acid to give the ester of second alcohol. The interchange of
alcohol portions of the esters is termed transesterification
The reaction is generally used for the preparation of the esters of a
higher alcohol from that of a lower alcohol.
3. Reaction with ammonia (Ammonolysis)
Esters react slowly with ammonia to form amides and alcohol.
4. Claisen Condensation
Esters containing at least one ∝- hydrogen atom undergo self
condensation in the presence of a strong base such as sodium
ethoxide to form b- keto ester
-9-
5. Reaction with PCl5
Esters react with PCl5 to give a mixture of acyl and alkyl chloride
Reactions of Esters:
Esters can be cleaved back into a carboxylic acid and an alcohol by
reaction with water and a catalytic amount of acid.
General Reaction
Mechanism
Protonation of the Carbonyl
- 10 -
Esters can be cleaved back into a carboxylic acid and an alcohol by
reaction with water and a base
The reaction is called a saponification from the Latin sapo which
means soap. The name comes from the fact that soap used to me
made by the ester hydrolysis of fats. Due to the basic conditions a
carboxylate ion is made rather than a carboxylic acid.
General reaction
Mechanism
Nucleophilic attack by hydroxide
Methods of preparation:
1. Esterification
We have already learnt that treatment of alcohols with carboxylic
acids in presence of mineral acid gives esters. The reaction is carried
- 11 -
to completion by using an excess of reactant or by removing the
water from the reaction mixture.
2. Alcoholysis of Acid chloride or Acid anhydrides
Treatment of acid chloride or acid anhydride with alcohol also gives
esters
References:
https://www.brainkart.com/article/Esters_41390
https://en.m.wikipedia.org/wiki/Ester
- 12 -

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Introduction:

What are esters?.

Ester are derived from carboxylic acids. A

A common ester - ethyl ethanoate

The most commonly discussed ester is ethyl

Notice that the ester is named the opposite

A few more esters

In each case, be sure that you can see how

Notice that the acid is named by counting up

Fats and oils

Animal and vegetable fats and oils are just big

If the melting points are below room

Fats and oils as big esters

Esters can be made from carboxylic acids and

Now let's make the alcohol a bit more complicated by having

structure of propane-1,2,3-triol (old name: glycerol).

back-to-front to make the next diagrams clearer. Normally, it is

drawn with the -OH groups on the right-hand side.

three ethanoate groups.

The Acid Ch3(Ch2)16COOH Is Called Octadecanoic Acid, But

The Old Name Is Still Commonly Used. This Is Stearic Acid.

The full name for the ester of this with propane-1,2,3-triol is

propane-1,2,3-triyl trioctadecanoate. But the truth is that almost

everybody calls it (not surprisingly!) by its old name of glyceryl

I am thinking here about things like ethyl ethanoate.

aldehydes and ketones with the same number of carbon atoms.

dipole-dipole interactions as well as van deer Waals dispersion

forces. However, they don't form hydrogen bonds, and so their

number of carbon atoms.

Molecule Type Boiling point( °C)

CH3COOCH2CH3 ester 77.1

CH3CH2CH2COOH carboxylic acid 164

formula solubility (g per 100

ethyl methanoate HCOOCH2CH3 10.5

bond with themselves, they can hydrogen bond with water

We have already learnt that hydrolysis of esters gives alcohol and

2. Reaction with alcohol ( Transesterification)

a mineral acid to give the ester of second alcohol. The interchange of

alcohol portions of the esters is termed transesterification

The reaction is generally used for the preparation of the esters of a

higher alcohol from that of a lower alcohol.

3. Reaction with ammonia (Ammonolysis)

Esters react slowly with ammonia to form amides and alcohol.

Esters containing at least one ∝- hydrogen atom undergo self

condensation in the presence of a strong base such as sodium

ethoxide to form b- keto ester

reaction with water and a catalytic amount of acid.

Protonation of the Carbonyl

reaction with water and a base

The reaction is called a saponification from the Latin sapo which

made by the ester hydrolysis of fats. Due to the basic conditions a

carboxylate ion is made rather than a carboxylic acid.

Nucleophilic attack by hydroxide

We have already learnt that treatment of alcohols with carboxylic

acids in presence of mineral acid gives esters. The reaction is carried

water from the reaction mixture.

2. Alcoholysis of Acid chloride or Acid anhydrides

Treatment of acid chloride or acid anhydride with alcohol also gives

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