Carboxylic Acids and Esters

Carboxylic acids
IGCSE
L.O.
Carboxylic Acids: Basics
• These are a homologous series of organic compounds

that all contain the same functional group: –COOH
• They have the general formula: CnH2n+1COOH
• They are colourless liquids which are weakly acidic and
have typical acidic properties
• They react with alkaline solutions, turn blue
litmus red and form salts called ethanoates
4 first represents of carboxylic acids
Ethanoic Acid
• Ethanoic acid (also called acetic acid) is the acid used

to make vinegar, which contains around 5% by volume
ethanoic acid
• Ethanoic acid is a typically weak acid and dissociates
slightly in water, producing a mildly acidic solution
• The equilibrium lies far to the left during ionisation:
u CH3COOH (aq) ⇌ H+ (aq) + CH3COO- (aq)
Reaction with metals
• The carboxylic acids behave like other acids
• They react with metals to form a salt and hydrogen and
with carbonates to form a salt, water and carbon dioxide
gas
• They also take part in neutralisation reactions with bases
to produce salt and water
• In the reaction with metals a metal salt and hydrogen gas
are produced
• For example, in reaction with magnesium the salt
magnesium ethanoate is formed:
u 2CH3COOH (aq) + Mg (s) → (CH3COO)2Mg (aq) + H2(g)
Reaction with hydroxides
• In the reaction with hydroxides a salt and water are

formed in a neutralisation reaction
• For example, in reaction with potassium hydroxide the
salt potassium ethanoate is formed:
u CH3COOH (aq) + KOH (aq) → CH3COOK (aq) + H2O (l)
Reaction with carbonates
•In the reaction with carbonates a salt, water and carbon dioxide
gas are produced
•For example, in reaction with potassium carbonate the salt
potassium ethanoate is formed:
2CH3COOH (aq) + K2CO3 (s) → 2CH3COOK (aq) + H2O (l) +CO2 (g)
Ethanoic Acid & Esterification Reactions
u Making Carboxylic Acids
• Two methods used to make carboxylic acids are:
• Oxidation by fermentation
• Using oxidising agents
• The microbial oxidation (fermentation) of ethanol will produce a
weak solution of vinegar (ethanoic acid)
• This occurs when a bottle of wine is opened as bacteria in the air
(acetobacter) will use atmospheric oxygen from air to oxidise the
ethanol in the wine
u C2H5OH (aq) + O2 (g) → CH3COOH (aq)+ H2O (l)
• The acidic, vinegary taste of wine which has been left open
for several days is due to the presence of ethanoic acid
• Alternatively, oxidising agent potassium manganate(VII) can
be used
• This involves heating ethanol with acidified potassium
manganate(VII) in the presence of an acid
• The heating is performed under reflux which involves
heating the reaction mixture in a vessel with a condenser
attached to the top
•The condenser prevents the
volatile alcohol from escaping the
reaction vessel as alcohols have low
boiling points
•The equation for the reaction is:
CH3CH2OH (aq) + [O] → CH3COOH
(aq) + H2O (l)
•The solution will change from
purple to colourless
•The oxidising agent is represented Diagram showing the
by the symbol for oxygen in square experimental setup for the
oxidation with KMnO4 using reflux
brackets apparatus
Properties of aqueous ethanoic acid
Describe the formation of ethanoic acid by the
oxidation of ethanol by fermentation and with
acidified potassium manganate(VII)
u Ethanol reacts with oxygen in the air to form

ethanoic acid (microbial oxidation)
u Ethanol reacts with acidified potassium
manganate(VII) to form ethanoic acid (under
reflux)
Describe ethanoic acid as a typical weak acid
u A typical weak acid

u This means ethanol will release some H + ions in
solution, but will not fully dissociate (loses the H
+ from the COOH group)
Describe the reaction of a carboxylic acid with an alcohol in the
presence of a catalyst to give an ester
u Carboxylic acids react with alcohols in the

presence of an acid catalyst to produce esters
Esters
IGCSE
Making Esters
• Alcohols and carboxylic acids react to make esters

in esterification reactions
• Esters are compounds with the functional group R-COO-R
• Esters are sweet-smelling oily liquids used in food
flavourings and perfumes
• Ethanoic acid will react with ethanol in the presence of
concentrated sulfuric acid (catalyst) to form ethyl
ethanoate:
u CH3COOH (aq) + C2H5OH (aq) ⇌ CH3COOC2H5 (aq) + H2O (l)
Naming Esters
• An ester is made from an alcohol and carboxylic acid

• The first part of the name indicates the length of the carbon
chain in the alcohol, and it ends with the letters ‘- yl’
• The second part of the name indicates the length of the
carbon chain in the carboxylic acid, and it ends with the
letters ‘- oate’
• E.g. the ester formed from pentanol and butanoic acid is
called pentyl butanoate

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Carboxylic Acids and Esters

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Carboxylic acids

• These are a homologous series of organic compounds

• Ethanoic acid (also called acetic acid) is the acid used

• In the reaction with hydroxides a salt and water are

u Ethanol reacts with oxygen in the air to form

u A typical weak acid

u Carboxylic acids react with alcohols in the

• Alcohols and carboxylic acids react to make esters

• An ester is made from an alcohol and carboxylic acid

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