1 of 31 © Boardworks Ltd 2009

2 of 31 © Boardworks Ltd 2009

Where are carboxylic acids found?

3 of 31 © Boardworks Ltd 2009

What are carboxylic acids?

Carboxylic acids contain a functional group of carbon,

hydrogen and oxygen atoms arranged like this...

...which is written as –COOH.

E.g.

methanoic acid (HCOOH) ethanoic acid (CH3COOH)

What do you think the carboxylic acid with three carbon atoms
is called?

4 of 31 © Boardworks Ltd 2009

General formula of carboxylic acids

• The general formula for the carboxylic acids is CnH2n+1COOH

(where n is the number of carbon atoms in the molecule,
minus 1).
• The general formula for carboxylic acids can also be written
as CnH2nO2 (where n is the number of carbon atoms in the
molecule)
• Example : what is the general formula of butanoic acid?
CnH2n+1COOH CnH2nO2
n=4-1=3 n=4
C3H7COOH C 4H8O2

5 of 31 © Boardworks Ltd 2009

Naming carboxylic acids

6 of 31 © Boardworks Ltd 2009

Making carboxylic acids

If you leave wine standing open to the air, oxygen from the air
will oxidize the ethanol to ethanoic acid, forming vinegar.

+  +

ethanol oxygen ethanoic acid water

In fact, any carboxylic acid can be made by oxidizing the

corresponding alcohol.
Q) Which carboxylic acid is made when methanol is oxidized?
A) Methanoic acid.

7 of 31 © Boardworks Ltd 2009

Properties of carboxylic acids

Carboxylic acids:
 have relatively high melting and boiling points
 are very soluble in water
 are weak acids
 have a characteristic smell!

Examples of everyday carboxylic acids include:

 citric acid (found in citrus fruits)
 lactic acid (found in tired muscles)
 malic acid (found in sour and tart foods).

8 of 31 © Boardworks Ltd 2009

Match the properties

9 of 31 © Boardworks Ltd 2009

Chemical properties of carboxylic acids

Carboxylic acids are typical weak acids.

What would happen if you added a few cm3 of dilute ethanoic

acid to each of these substances?

 A few drops of universal

indicator.
 3 cm3 sodium hydroxide
solution.
 Half a spatula of sodium
carbonate.
 A piece of magnesium
ribbon.

10 of 31 © Boardworks Ltd 2009

Reactions of carboxylic acids

11 of 31 © Boardworks Ltd 2009

Reactions of carboxylic acids

Carboxylic acids react like any other type of acid, forming

salts when they react with alkalis, carbonates and metals:
sodium sodium
ethanoic acid +  + water
hydroxide ethanoate
CH3COOH + NaOH  CH3COONa + H 2O

sodium sodium carbon

ethanoic acid +  + + water
carbonate ethanoate dioxide
2CH3COOH + Na2CO3  2CH3COONa + CO2 + H 2O

sodium
ethanoic acid + sodium  + hydrogen
ethanoate
2CH3COOH + 2Na  2CH3COONa + H2

12 of 31 © Boardworks Ltd 2009

Reactions of carboxylic acids

13 of 31 © Boardworks Ltd 2009

Reactions of carboxylic acids

14 of 31 © Boardworks Ltd 2009

15 of 31 © Boardworks Ltd 2009
Carboxylic acids in descalers

In hard water areas, limescale (calcium carbonate) builds up

in kettles and water pipes.

To remove the limescale, a

descaler can be used, which
contains ethanoic acid.

What reaction takes place

between the ethanoic acid
and limescale?

calcium calcium carbon

ethanoic acid +  + + water
carbonate ethanoate dioxide
2CH3COOH + CaCO3  (CH3COO)2Ca + CO2 + H 2O

16 of 31 © Boardworks Ltd 2009

Carboxylic acids in soaps

Fatty acids are carboxylic acids with very long carbon chains.
The sodium and potassium salts of fatty acids can be used
as soaps.
For example, reacting octadecanoic acid with sodium
hydroxide produces sodium octadecanoate, a common soap.

(octadecanoic acid)

(sodium octadecanoate)

17 of 31 © Boardworks Ltd 2009

18 of 31 © Boardworks Ltd 2009
What are esters?

Esters have characteristic smells, and are

often used in flavourings and perfumes.

For example:
 propyl ethanoate smells of pears
 butyl butanoate smells of pineapple
 methyl butanoate smells of apple.

19 of 31 © Boardworks Ltd 2009

Esters

Esters contain this group of atoms:

...which is written as –COO–.

Esters are made from the reaction of a carboxylic acid with an

alcohol:
carboxylic acid + alcohol  ester + water

propanoic acid + methanol  methyl propanoate + water

CH3CH2COOH + CH3OH  CH3CH2COOCH3 + H2O

+  +

20 of 31 © Boardworks Ltd 2009

Naming esters

Esters are named after the alcohol and the carboxylic acid
from which they are made. The alcohol gives the first part
of the name, and the carboxylic acid gives the second.
Esters always end in “–anoate”.
For example:

ethanoic acid methanol

methyl ethanoate
21 of 31 © Boardworks Ltd 2009
Matching carboxylic acids to their esters

22 of 31 © Boardworks Ltd 2009

Practising naming esters

23 of 31 © Boardworks Ltd 2009

24 of 31 © Boardworks Ltd 2009
How are esters made?

Esters are made by reacting a

carboxylic acid with an alcohol.

However, the reaction is very

slow at room temperature.

How could you speed it up?

 The reactants could be

heated in order to make the
reaction faster.
 A catalyst of concentrated
sulfuric acid could be added.

25 of 31 © Boardworks Ltd 2009

What are the stages in making an ester?

26 of 31 © Boardworks Ltd 2009

Hydrolysis of esters

• The breaking up of an
ester can be achieved
by heating the ester
with an alkali such as
sodium hydroxide.
• This is an example of
a hydrolysis
reaction (the opposite
of a condensation
reaction) as a water
molecule is added
and breaks up the
structure.

27 of 31 © Boardworks Ltd 2009

28 of 31 © Boardworks Ltd 2009
Glossary

29 of 31 © Boardworks Ltd 2009

Multiple-choice quiz

30 of 31 © Boardworks Ltd 2009