Carboxylic acids
and esters
Chemistry
Unit Organic chemistry
:
Outcome
I can describe the structure of the first four
carboxylic acids, and recognise and describe
reactions where carboxylic acids are involved.
Keywords
carboxylic
acids
weak acids
carbonate
esters
ethyl
ethanoate
Keywords
Carboxylic acids are a homologous series of
compounds that contain the -COOH functional group.
Weak acids partially dissociate to form H+ ions in solution.
A carbonate is a compound containing the CO32- ion. An example
is calcium carbonate CaCO3.
Esters are a homologous series of compounds that contain the -
COO- functional group.
Ethyl ethanoate is an ester produced when the alcohol
ethanol reacts with the carboxylic acid ethanoic acid.
Lesson outline
Carboxylic acids and esters
Introduction to carboxylic acids
Reactions of carboxylic acids
Esters
Introduction to carboxylic acids
Explanation
Carboxylic acids are a homologous series of
compounds that contain the -COOH functional
group.
Here is a model of the simplest carboxylic acid:
The COOH functional
group.
Introduction to carboxylic acids
Explanation
Citric acid is a carboxylic acid found in fruits
such as lemons.
lemons citric acid molecule
Introduction to carboxylic acids
Check
Which functional group is present in carboxylic acids?
a C=C
b COOH
c OH
Introduction to carboxylic acids
Explanation
When naming carboxylic acids they have the
suffix -oic acid.
The first four carboxylic acid in the homologous
series are:
butanoic
methanoic acid acid
(HCOOH)
propanoic (CH
acid 3CH
(CH 2CH 2COOH)
ethanoic
3CH 2COOH)
acid (CH3COOH)
Introduction to carboxylic acids
Check
The image shows a molecule of
…
a methanol.
b ethanol.
c methanoic acid.
d ethanoic acid.
Introduction to carboxylic acids
Check
What name is given to the carboxylic acid
containing three carbon atoms (C2H5COOH)?
a butanoic acid
b methanoic acid
c propanoic acid
d ethanoic acid
Introduction to carboxylic acids
Explanation
Carboxylic acids dissolve in water to produce
solutions that are weakly acidic.
Weak acids partially dissociate to produce H+ ions when in
solution.
An example showing ethanoic acid added to water:
H2O
+
CH3COOH CH3COO- + H+
Introduction to carboxylic acids
Explanation
Weak acids such as carboxylic acids have higher
pH values than stronger acids with the same
concentration.
acid neutral alkali
pH chart
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14
Introduction to carboxylic acids
Check
True or false?
Carboxylic acids are weak acids that fully dissociate in
solution to produce H+ ions.
T True F False
Justify your answer
a Carboxylic acids are strong acids that fully dissociate
in solution to produce H+ ions.
b Carboxylic acids are weak acids that partially
dissociate in solution to produce some H+ ions.
Task A Introduction to carboxylic acids
Practice
1. Complete the table:
carboxylic ethanoi
acid name c acid
structural HCOOH CH3CH2CH2COOH
formula
displayed
formula
Task A Introduction to carboxylic acids
Feedbac
k
1. Complete the table:
carboxylic methanoic acid ethanoic acid
acid name
structural HCOOH CH3COO
formula
H
displayed
formula
Task A Introduction to carboxylic acids
Feedbac
k
1. Complete the table:
carboxylic propanoic acid butanoic acid
acid name
structural
CH3CH2COOH CH3CH2CH2COOH
formula
displayed
formula
Task A Introduction to carboxylic acids
Practice
2. Show what happens when each of these
carboxylic acids is added to water.
a.
H2O
H2O
b. C3H7COOH
Task A Introduction to carboxylic acids
Feedbac
k
2. Show what happens when each of these
carboxylic acids is added to water.
a.
H2O
+
H2O
b. C3H7COOH C3H7COO- + H+
Lesson outline
Carboxylic acids and esters
Introduction to carboxylic acids
Reactions of carboxylic acids
Esters
Reactions of carboxylic acids
Explanation
Carboxylic acids can be formed from the oxidation
of alcohols using oxidising agents.
An example showing the oxidation of ethanol:
+ oxidising
agent
ethanol ethanoic acid
an alcohol a carboxylic acid
Reactions of carboxylic acids
Check
Propanoic acid can be produced from the oxidation
of …
a ethanoic acid.
b butanoic acid.
c propanol.
Reactions of carboxylic acids
Explanation
Carboxylic acids can react with metal carbonates
to produce salt, water and carbon dioxide.
The word equation for this reaction is:
metal + carboxylic salt + carbon + water
carbonate acid dioxide
Reactions of carboxylic acids
Explanation
An example of a reaction between a metal carbonate
and carboxylic acid is:
sodium + methanoic sodium + carbon + water
carbonate acid methanoate dioxide
A reaction between a metal
carbonate and carboxylic acid.
Reactions of carboxylic acids
Explanation
Looking at the displayed formula helps us see how
the salt forms.
sodium + methanoic sodium + carbon + water
carbonate acid methanoate dioxide
Na2CO3 + 2HCOOH 2HCOONa + CO 2 +
H2O
Na2CO3 + 2 2 + CO2 + H2O
H Na
Reactions of carboxylic acids
Check
Which gas is produced when carboxylic acids react
with metal carbonates?
a oxygen
b hydrogen
c carbon dioxide
Reactions of carboxylic acids
Explanation
Carboxylic acids react with alcohols in the
presence of an acid catalyst to form esters.
acid catalyst
alcohol + carboxylic acid ester + water
An example of a carboxylic acid forming an ester:
methanol + propanoic acid catalyst methyl +water
acid propanoate
alcohol carboxylic acid ester
Reactions of carboxylic acids
Check
When a carboxylic acid reacts with an alcohol in the
presence of an acid catalyst, which organic compound is
produced?
a haloalkane
b alkene
c ester
d alcohol
Task B Reactions of carboxylic acids
Practice
1. Identify which of these molecules are carboxylic acids.
a. CH3CH2OH b. CH2=CHCH3 c. HCOOH
d. CH3COOH e. CH3OH f. CH3CH2CH3
g. h.
Task B Reactions of carboxylic acids
Practice
2. Complete the following equations:
a. _______ + methanoic sodium + ______ + water
acid methanoate
b._______ + _______ calcium + ______ +______
carbonate propanoate
c. ________ + carboxylic acid catalyst _______ +water
acid
d. _______ + ethanoic acid catalyst ethyl +_____
acid ethanoate
Task B Reactions of carboxylic acids
Feedbac
k
1. Identify which of these molecules are carboxylic acids.
a. CH3CH2OH b. CH2=CHCH3 c. HCOOH
d. CH3COOH e. CH3OH f. CH3CH2CH3
g. h.
Task B Reactions of carboxylic acids
Feedbac
k
2. Complete the following equations:
a.sodium
_______ + methanoic sodium carbon + water
+ ______
carbonat acid methanoate dioxide
e
b.calcium
_______ +propanoic
_______ calcium + carbon
______ + water
_____
carbonate acid propanoate dioxide
c. alcohol
_____ + carboxylic acid catalyst ester
_______ +water
acid
d. ethanol
_______ + ethanoic acid catalyst ethyl + water
_____
acid ethanoate
Lesson outline
Carboxylic acids and esters
Introduction to carboxylic acids
Reactions of carboxylic acids
Esters
Esters
Explanation
Esters can be synthetic or found naturally. They
are found naturally in many fruits.
Esters are used in foods as flavouring,
and in perfumes due to their sweet
smell.
strawberries containing esters perfume containing
esters
Esters
Explanation
Esters contain the functional group -COO-.
Esters can be produced from reacting an alcohol and
carboxylic acid together in the presence of an acid
catalyst.
Esters
Explanation
alcoho carboxylic acid
l
+
ester water
Esters
Check
To produce an ester, what does a carboxylic acid
react with?
a alkane
b metal carbonate
c alcohol
d water
Esters
Explanation
When naming esters:
● the alcohol part goes first and ends in -yl
● the carboxylic acid part goes last and ends in -oate
Example 1:
ethanol + propanoic acid ethyl propanoate +
water
Example 2:
butanol + methanoic acid butyl methanoate +
water
Esters
Explanation
Example 3: This ester is called ethyl ethanoate.
ethyl ethanoate
Esters
Check
What is the name of this ester?
a propyl methanoate
b methyl propanoate
c ethyl ethanoate
Task C Esters
Practice
1. Ethanoic acid reacts with ethanol in the presence of
concentrated sulfuric acid.
a. What is the role of the concentrated sulfuric acid?
b. Draw the displayed structure of the ester that forms.
c. Name the ester formed.
d. What is a possible use of this ester?
Task C Esters
Feedbac
k
1. Ethanoic acid reacts with ethanol in the presence of concentrated
sulfuric acid.
a. What is the role of the concentrated sulfuric acid?
It is a catalyst.
b. Draw the displayed structure of the ester that forms.
d. What is a possible use of
this ester?
Your answer may include: in
perfumes, or as flavourings in
c. Name the ester formed. food.
Ethyl ethanoate
Summar
y Carboxylic acids and esters
Carboxylic acids have a -COOH functional group.
Carboxylic acids are weak acids.
When ethanol is oxidised, ethanoic acid is formed.
Carboxylic acids react with carbonates to produce a
metal salt, carbon dioxide and water.
Carboxylic acid can react with alcohol to produce esters
(such as ethyl ethanoate).
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