IGCSE Revision guide: Chemistry Families of organic compounds 20

• Being an acid, it neutralises bases to form salts such as sodium ethanoate:

20.7 Carboxylic acids H O H O
H C C (aq) + NaOH (aq) H C C (aq) + H2O (l
The carboxylic acids are a family of organic compounds.
Extended

H OH H ONa
• They contain the COOH functional group, which has a C=O double bond in it. O
C ethanoic acid sodium sodium ethanoate water
• Their names end in -oic acid hydroxide (a salt)
• They form the homologous series with the general formula CnH2nO2 OH
The carboxyl functional group. or CH3COOH (aq) + NaOH (aq) → CH3COONa (aq) + H2O (l)
The most common carboxylic acid is ethanoic acid, CH3COOH
• Ethanoic acid reacts with alcohols to form compounds called esters.

Extended
For example with propan-1-ol it forms the ester propyl ethanoate:
How ethanoic acid is obtained
Ethanoic acid is produced by the oxidation of ethanol: H this group is called
O
an ester linkage
H H H H conc. H
H H H C O H2SO4 O
O
[O] + H H H + H2 O
H C H C HO C C C
O
H H H OH H H OH H H H H C C C water
H
ethanol ethanoic acid ethanoic acid propanol H H H
The bonding in ethanoic acid. propyl ethanoate (an ester)
There are two ways to carry out the oxidation: Note the C=O double bond.
conc. H2SO4
or CH3COOH (l ) + C3H7OH (l ) CH3COOC3H7 (l ) + H2O (l )
1 By fermentation – the ‘biological’ way

• If ethanol is left standing in air, bacteria will bring about its oxidation to ethanoic More about esters
acid. This process is called acid fermentation. It is used to make vinegar from fruits • Esters are formed when an alcohol reacts with a carboxylic acid.
and other foodstuffs. (Vinegar is a dilute solution of ethanoic acid.) • During the reaction, two molecules join to make a larger molecule, with the loss
of a small molecule, water. So this is called a condensation reaction
2 Using oxidising agents – the ‘chemical’ way the ester linkage
• The reaction is reversible, and sulfuric acid acts as a catalyst. H O
• Ethanol is oxidised much faster by warming it with potassium manganate(VII), • The alcohol part comes rst in the name of the ester – but second in the H H H
a powerful oxidising agent, in the presence of acid. structural formula. (Compare with sodium ethanoate above.) O H
H
• The manganate(VII) ions are reduced to Mn2+ ions, with a colour change. • The functional group in an ester is the ester linkage. It is circled in the diagrams
H H
The acid provides the hydrogen ions for this reaction: above and on the right.
• Many esters have distinctive tastes and smells, so they are used as articial the structural formula of
MnO4 + 8H+ + 5e → Mn2+ + 4H2O
avourings and fragrances. ethyl ethanoate
purple colourless

Using another oxidising agent Quick check for 20.7 (Answers on page 170)
Ethanol is also oxidised by potassium dichromate(VI), another powerful oxidising agent, in the 1 What is the functional group in a carboxylic acid?
presence of acid. Again there is a colour change, when the chromate(VI) ions are reduced: 2 Name the product that forms, when the alcohol methanol is oxidised.
Cr2O72– + 14H+ + 6e → 2Cr3+ + 7H2O 3 How is the ethanoic acid in vinegar made?
orange green 4 Why does the colour change, when ethanol is oxidised by acidied potassium
dichromate(VI)?
Potassium dichromate is used in one type of breathalyser. It oxidises any alcohol on a
5 How could you tell that ethanoic acid is a weak acid?
person’s breath and is itself reduced, changing colour from orange to green.
6 How is an ester made?
7 Name and draw out the structural formula of the ester made from butanol
Reactions of ethanoic acid and propanoic acid.
• Ethanoic acid is a weak acid. That means it partly ionises (or dissociates) in water,
to form ethanoate ions and hydrogen ions:

H O H O
H (aq) H C C (aq) + H+ (aq)
H OH H O
ethanoic acid ethanoate ion hydrogen ion

or CH3COOH (aq) ⇋ CH3COO (aq) + H+ (aq)

150 151
IGCSE Revision guide: Chemistry Families of organic compounds 20

4 The diagram shows a bottle of mineral water.

Questions on Section 20 top made of poly(propene)

Answers for these questions are on page 170.

Core curriculum
1 The compound shown on the right is the rst member of the alkane homologous series.
H label
a State two characteristics of a homologous series.
b Name and draw the structure of the next member of the alkane homologous series. H
c Complete the table to show the structure and uses of some organic compounds. H
bottle made of poly(ethene)
name of molecular formula structure use
compound (showing all atoms and bonds) a The poly(propene) top is made by polymerising propene molecules, CH3CH CH2
i Which one of the following best describes the propene molecules in this reaction?
ethene C2H4 i ii
alkanes monomers polymers products salts
ethanoic acid C2H4O2 iii making esters ii State the name of the homologous series to which propene belongs.
iii Propene is an unsaturated hydrocarbon.
Br Br State the meaning of the terms unsaturated and hydrocarbon
dibromoethane iv H C iv Describe a chemical test to distinguish between an unsaturated hydrocarbon
H H and a saturated hydrocarbon. State the results.
b The poly(ethene) bottle is made by polymerising ethene.
H
nCH2 CH2 ( CH2 CH2 ) n
v CH4 H C H vi
Complete the following sentence about this reaction by lling in the blank space.
H The formation of poly(ethene) is an example of an ................ polymerisation reaction.
Adapted from Cambridge IGCSE Chemistry 0620 Paper 2 Q2a and b November 2007
Adapted from Cambridge IGCSE Chemistry 0620 Paper 2 Q6a, b, and c November 2008

2 Petrol is a mixture of alkanes. One of the alkanes in petrol is octane, C8H18 Extended curriculum

a What products are formed when octane is completely burnt in air?
b More petrol can be made by cracking less useful petroleum fractions.
i What do you understand by the term cracking?
ii State two conditions needed for cracking.
iii Alkenes can be formed by cracking. The simplest alkene is ethene. Draw
a diagram to show the structure of ethene. Show all atoms and bonds.
Cambridge IGCSE Chemistry 0620 Paper 2 Q3b and d June 2007
3 a Match the compounds on the left with the statements on the right.
The rst one has been done for you.
butane a hydrocarbon containing four carbon atoms
poly(ethene) it decolourises bromine water
ethene it is the main constituent of natural gas
methane it contains a –COOH functional group
ethanoic acid it has a very long chain of carbon atoms
b Methane and ethene are hydrocarbons.
i What is meant by the term hydrocarbon?
ii The structure of ethene is shown on the right.
Use this structure to explain why ethene is an unsaturated hydrocarbon.
Adapted from Cambridge IGCSE Chemistry 0620 Paper 22 Q4a and b November 2013
Extended
1 For each of the following predict the name of the organic product.
a reaction between methanol and ethanoic acid
b oxidation of propan-1-ol by potassium dichromate (VI)
c removal of H2O from ethanol (dehydration)
Adapted from Cambridge IGCSE Chemistry 0620 Paper 3 Q6d November 2007
2 The fermentation of glucose is catalysed by enzymes from yeast. Yeast is added to
aqueous glucose, the solution starts to bubble and becomes cloudy as more yeast cells
are formed.
C6H12O6 (aq) → 2C2H5OH (aq) + 2CO2 (g)
The reaction is exothermic. Eventually the fermentation stops when the concentration
of ethanol is about 12%.
a What is an enzyme?
b Pasteur said that fermentation was respiration in the absence of air. Suggest a
denition of respiration
c On a large scale, the reaction mixture is cooled. Suggest a reason why this is
necessary.
d Why does the fermentation stop? Suggest two reasons.
e When the fermentation stops, there is a mixture of dilute aqueous ethanol and
yeast. Suggest a technique which could be used to remove the cloudiness due to
the yeast.
H H
f Name a technique which will separate the ethanol from the ethanol / water mixture.
Adapted from Cambridge IGCSE Chemistry 0620 Paper 31 Q6c June 2008
H H

152 153