Esters

C.I. 13.5

What are they?

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

Names of esters
end in oate.

Naming

Named after alcohol & carboxylic acid

from which they are derived.
O
C
CH3

CH2

CH3

lets name
some esters!

ethyl
this part comes from
the alcohol & is named
after it

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
ethyl ethanoate
Either

Or

O
CH3

O
C

version the
acid part
has been
written first

CH2

CH3

CH3 CH2 O C CH3

Identify the group attached to the C=O this is from
the acid
The group attached to the O- is from the alcohol.

Wait! Whats that smell?

ester
ethyl methanoate
3-methylbutyl ethanoate
ethyl 2-methylbutanoate
phenylmethyl ethanoate

fragrance
raspberries
pears
apples
jasmine

Esters have strong, sweet smells.

Their bouquet is often floral or fruity.
This means they are used in food flavourings &
perfumes.
Also, very good at dissolving organic
compounds so often used as solvents.

Esters from phenols

-OH group in phenol less reactive
to esterification, requires a more
vigourous reagent.
Use of ethanoic acid in
esterification is also known as
ethanoylation.
Ethanoic anhydride is a more
vigourous ethanoylating agent

OH

Esters from phenols

Ethanoic anhydride used as it is reactive
but not too dangerous.
Ethanoyl chloride is much more reactive,
but, also toxic and hazardous to
use.
Ethanoic anhydride & ethanoyl chloride
are described as acylating agents

using an acylating agent is the only way to

esterify a phenol
alcohols can be esterified using acylating
agents or by reacting with a carboxylic acid.

Ester hydrolysis
Breakdown of an ester by water.
Process sped up by catalysis
Can use an acid to catalyse (H2SO4)
Alkali catalysts (e.g. sodium hydroxide)

can also be used but instead of producing

carboxylic acid a carboxylate salt is
formed.
Alkaline hydrolysis goes to completion &
hence is usually preferred.

O
+

O
C

C
R

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

+
H2O

Definition of a condensation reaction =

two molecules reacting to form a larger
molecule with the elimination of a
small molecule such as water

O
CH
CH3

CH2

ethyl

methanoate

O
C
CH3

CH2

CH3 methyl

propanoate

O
O
CH

CH3

methyl

methanoate

FORWARD REACTION = condensation reaction,

the esterification of an alcohol using
acid catalyst under reflux.
R

O
+

O
C

C
R

O
+
H2O

REVERSE REACTION = ester hydrolysis, same

catalyst works for both forward & reverse
reactions.

ethanol

ethyl ethanoate
O
C
CH3 CH2

+
OH

CH3

CH3 CH2
+

O
C
O

not a reaction that exists

in equilibrium (unlike
using acid catalyst)

OH

CH3

ethanoate ion