|


 

 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 m


 m

!˜he condensation reaction between the
hydroxyl group and the carboxylic acid
known as  
m

!ôeverse reaction = ester hydrolysis
 P

P
 
 •



Pamed after alcohol & carboxylic acid from

which they are derived.
O V



 

m mH3
mH3 mH2 O
?
 ?
 ?

this part comes from the this part from the acid
alcohol & is named after it and is named after it
 

 V

V
Although the previous structural formula are the clearest
way of showing esters, they can draw out in a
shortened form. In this version
?
 ?
 ? the acid part
has been
OrƦ
O written first
|itherƦ O
mH3 m O mH2 mH3
mH3 mH2 O m mH3
! Identify the group attached to the C=O ƛ this is from
the acid
! ˜he group attached to the ƛO- is from the alcohol.
 Wait! What·s that smell?
ester fragrance
ethyl methanoate raspberries
3-methylbutyl ethanoate pears
ethyl 2-methylbutanoate apples
phenylmethyl ethanoate jasmine

{ |sters have strong, sweet smells.

{ ˜heir bouquet is often floral or fruity.
{ ˜his means they are used in food flavourings &
perfumes.
{ Also, very good at dissolving organic compounds so
often used as solvents.
 |sters from phenols
-OH group in phenol V

reactive
to esterification, requires a more

reagent.
‡ Use of ethanoic acid in OH
esterification is also known as

 V .
‡ |


  is a more
vigourous ethanoylating agent
 |sters from phenols
‡ Ethanoic anhydride used as it is reactive
but not too dangerous.
‡ |
 V
V is much more reactive,
but, also p
 and 
to use.
‡ Ethanoic anhydride & ethanoyl chloride
are described as O
OO

!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.
 |
 V

!reakdown of an ester by water.

!Process sped up by catalysis
!man 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.
 ô O H O
m ô
 O
m ô ~ ô O

H O ˜his is why it is a H2 O
condensation reaction
because water is produced!

©?   
?  ?
 
 ?
? ?
      ?
?
? 

? ?   
 ?
? 

  ?
 O
mH ?
 ?
 ?

mH3 mH2 O

O
m mH2 mH3 ?
   ?

mH3 O

O
mH ?
 ?
 ?

mH3 O
(

©
  
?  ?


? ? ? 
    

 


  ? ?

ô O H O
m ô
 O
m ô À ô O

H O
H2 O

 


   ? ?
  ?

     
    ?? ?
?

?
 ?
 ? ?


O
mH3 mH2 OH
m mH3
mH3 mH2 O


OH- î O
m mH3
-O

not a reaction that exists ?
 ? 

in equilibrium (unlike
using acid catalyst)