Functional Groups: Naming of Esters

FUNCTIONAL GROUPS
All the new functional groups Esters, Acyl chlorides, Amides, Aldehydes and Ketones include a
common carbonyl group where a Carbon atom is attached to an Oxygen atom with a double
covalent bond.
ESTERS /ALKYL ALKANOATES
 Alcohols react with carboxylic acids to form esters.

 The OH group attached to the carboxylic acid is removed.
 The carboxylic acid and the alcohol are attached through the Oxygen atom of the OH group
on the alcohol.
 The breaking of the OH bond in the alcohol results in the removal of the hydrogen atom.
 This Hydrogen atom joins with the OH group of the carboxylic acid to form water.
 Water is removed as a waste product
The general equation is
Carboxylic acid + alcohol ester + water
How esterification takes place
Naming of esters
 The names of esters connect them with the parent alcohol and carboxylic acid from
which they are derived.
 The alcohol part comes first in the name of an ester whereas the acid part comes as
the second in its name.
 To name the acid part of the ester count the carbon in the carboxylate group.
 Since there are two parent chains present the ester can be written as follows:
alcohol part – ‘yl’ and the carboxylic acid part as ‘anoate’
 The number of Carbon atoms in the main chain of the alcohol is to be put in front of
the ‘-yl’ and the number of carbon atoms in the main chain of the carboxylic acid is
to be put in front of ‘-anoate’
If a four- carbon alcohol and a three-carbon carboxylic acid are used to produce an ester,
the ester would be names as butyl propanoate.
butanol + propanoic acid butyl propanoate + water.
C4H9OH(aq) + C2H5CO2H(aq) C2H5CO2C4H9(aq) + H2O(l)
The structure of butyl propanoate.
Methanol and propanoic acid are used to produce the ester methyl ethanoate.
Concentrated sulfuric acid is a catalyst for this reaction.
methanol + propanoic acid methyl propanoate + water.

CH3OH(aq) + C2H5CO2H(aq) C2H5CO2CH3(aq) + H2O(l)
The structure of methyl propanoate.
Manufacture of an ester –
A -Esters are prepared by heating a carboxylic acid and an alcohol under reflux using
concentrated sulphuric acid as a catalyst. This condensation reaction results in the removal
of a molecule of water. This reaction is reversible.
B - Distil off the ester as soon as it is formed. This prevents the reverse reaction happening.
(It works well because the ester has the lowest boiling point of anything present. The ester is
the only thing in the mixture which doesn't form hydrogen bonds, and so it has the weakest
intermolecular forces.)
C - Shake with Sodium carbonate Na2CO3 solution to remove excess acid in separating funnel
opening the tap at times since pressure is build up due to production of CO 2. Run off
aqueous layer then shake with calcium chloride to remove unchanged ethanol
D - Granules of calcium chloride is added as a drying/dehydrating agent
E - The Ester is distilled off. Anti-bumping granules are added to prevent spilling/ formation
of large bubbles/ for smooth heating
Production of ester from refluxing a carboxylic acid and an alcohol
Heating under Reflux – Condenser is vertical, and the volatile contents drip back into the vessel.
Fractional distillation apparatus

USES OF ESTERS
 An ester is a sweet-smelling substance.

 Some esters are used as food flavourings (for example in pear drop sweets).
 Other esters are used as fragrances or perfumes.
 Esters can be made into polymers called polyesters.
 Polyesters can be used to make plastic bottles or polyesters can be made into fibres
to make clothing.
 Recycled polyesters are used to make fleece clothing.
Hydrolysis of esters: Esters can be hydrolysed by the reaction with water in both alkaline
and acidic conditions.
Carbon - Oxygen bond is broken
After the hydrolysis, the oxygen atom in the ester goes towards the alcohol. So, the bond
between carbonyl carbon and oxygen atom is broken. See the figure to understand this
bond breaking. This is same for both acidic and alkali hydrolysis of esters.
Hydrolysis of an ester with an alkali (soluble base) – When esters are hydrolysed by reacting
them with an aqueous solution of sodium hydroxide, a carboxylate ion/salt and an alcohol
are produced.
Note - in this reaction, first carboxylic acid and alcohol are given as products. But produced
carboxylic acid reacts with the strong alkali to form carboxylic acid salt. Therefore,
carboxylic acid reacts with NaOH or KOH to give sodium salt or potassium salt of the
carboxylic acid)
Eythyl propanoate alkaline hydrolysis

Hydrolysis of the ester Ethyl propanoate with a strong alkali like aqueous sodium hydroxide
gives ethanol and sodium propanoate.
Alkaline Potassium hydroxide KOH (aq) can also be used as an alkali for ethyl propanoate
alkaline hydrolysis.
Ethyl propanoate Sodium propanoate Ethanol

Acidic hydrolysis of esters
Dilute sulfuric acid is used for acidic ester hydrolysis. This reaction is done on heating. A
carboxylic acid compound and an alcohol compound are given as products. And this reaction
is a reversible one.
Dilute sulfuric acid (H2SO4) behaves as a catalyst to increase the reaction rate. Remember
that Conc.H2SO4 increases the reaction rate of both forward reaction and backward reaction.
The general equation for the reaction is as follows: -
Ethyl ethanoate acidic hydrolysis

Ethyl ethanoate reacts with dilute sulfuric acid to give ethanoic acid and ethanol which are a
carboxylic acid and an alcohol respectively.
Ethyl ethanoate Ethanoic acid Ethyl alcohol

Ethyl propanoate acidic hydrolysis
Ethyl propanoate acidic hydrolysis gives ethanol and propanoic acid. Dilute H 2SO4 is used on
heating to get the products.
Ethyl propanoate Propanoic acid Ethyl alcohol

Functional Groups: Naming of Esters

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FUNCTIONAL GROUPS

ESTERS /ALKYL ALKANOATES

 Alcohols react with carboxylic acids to form esters.

How esterification takes place

methanol + propanoic acid methyl propanoate + water.

Fractional distillation apparatus

 An ester is a sweet-smelling substance.

Eythyl propanoate alkaline hydrolysis

Ethyl propanoate Sodium propanoate Ethanol

Ethyl ethanoate acidic hydrolysis

Ethyl ethanoate Ethanoic acid Ethyl alcohol

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