I

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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 vander 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

Solubility in water
The small esters are fairly soluble in water but solubility falls
with chain length.
FOR-EXAMPLE:
solubility (g per 100 g of
ester formula
water)

ethyl methanoate HCOOCH2CH3 10.5

ethyl ethanoate CH3COOCH2CH3 8.7

ethyl propanoate CH3CH2COOCH2CH3 1.7

Some other Properties of Ester:
Esters are neutral(do not change color of litmus,
phenolphthalein, methyl orange or any other acid-
base indicator) compounds
Esters are colorless and exist in liquid state at
room temperature
Esters are polar due to the presence of carbonyl
(=C=O)group and act as hydrogen bond acceptors
not as donors.
Esters are volatile in nature and have low boiling
and melting points.
 MECHANISM OF THE BASE
HYDROLYSIS OF ESTERS

Step 1:
The hydroxide Nucleophilic
attacks at the electrophilic C of
the ester C=O, breaking the p
bond and creating the
tetrahedral intermediate.
Step 2:
The intermediate collapses,
reforming the C=O
results in the loss of the leaving
group the alkoxide, leading to
the carboxylic acid.
Step 3:
An acid / base reaction. A very
rapid equilibrium where the
alkoxide functions as a base
deprotonating the carboxylic
acid (an acidic work up would
allow the carboxylic acid to be
obtained from the reaction).
 ACID –HYDROLYSIS OF AN ESTER:
FIRST STEP:

The actual catalyst in this case is the hydroxonium ion, H3O+, present in all
solutions of acids in water. In the first step, the ester takes a proton (a hydrogen
ion) from the hydroxonium ion. The proton becomes attached to one of the lone
pairs on the oxygen which is double-bonded to the carbon.
 SECOND STEP:

The positive charge on the carbon atom is

attacked by one of the lone pairs on the oxygen of
a water molecule.
 THIRD STEP:
What happens next is that a proton (a hydrogen ion) gets
transferred from the bottom oxygen atom to one of the
others. It gets picked off by one of the other substances in
the mixture (for example, by attaching to a lone pair on a
water molecule), and then dumped back onto one of the
oxygens more or less at random. Eventually, by chance, it
will join to the oxygen with the ethyl group attached. When
that happens, the net effect is:
 The structure for the latest ion is just like the one we discussed at
length back in step 1. The positive charge is actually delocalized all
over that end of the ion. The real structure will be a hybrid of these:

FIFTH STEP
The hydrogen is removed from the oxygen by reaction with a water
molecule.
EXAMPLE:
Ethyl Ethanoate
Preparation Of Ethyl
Acetate:
 USES :
In Glues
In Nail polish Removers
In decaffeinating tea and coffee
In cigarettes.
As a solvents in industry, notably for
lacquers and resins
Artificial fruit flavor
In organic synthesis.
In organic synthesis e.g., for making
ethyl acetoacetate.