HSC CHEMISTRY LESSON PLAN 18

5.1.1 Describe the differences between the alkanol and alkanoic acid functional groups in carbon compounds

Alkanols are produced from alkenes and are characterised by the OH- hydroxy group. This is their functional group.
Examples include: CH3OH (methanol) and C2H5OH (ethanol)

Carboxylic (alkanoic) acids are derived from alkanes and are characterised by the carboxylic
acid functional group (-COOH). Examples include HCOOH (Methanoic acid), CH3COOH
(Ethanoic acid) and CH3CH2COOH (propanoic acid)

Use this space to make your own notes

5.1.2 Identify the IUPAC nomenclature for describing the esters produced by reactions of straight-chained alkanoic
acids from C1 to C8 and straight-chained primary alkanols from C1 to C8

When naming esters the alkanol part is named first with the ‘anol’ suffix being taken and ‘yl’ added. The alkanoic
acid is name next with the ‘oic’ suffix taken off and ‘oate’ added.

Alkanol Alkanoic acid

Methanoic Ethanoic Propanoic Butanoic Pentanoic Hexanoic Heptanoic Octanoic
acid acid acid acid acid acid acid acid
HCOOH CH3COOH C2H5COOH C3H7COO C4H9COOH C5H11COO C6H13COOH C7H15COO
H H H
Methano Methyl Methyl Methyl Methyl Methyl Methyl Methyl Methyl
l CH3OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Ethanol Ethyl Ethyl Ethyl Ethyl Ethyl Ethyl Ethyl Ethyl
C2H5OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Propanol Propyl Propyl Propyl Propyl Propyl Propyl Propyl Propyl
C3H7OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Butanol Butyl Butyl Butyl Butyl Butyl Butyl Butyl Butyl
C4H9OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Pentanol Pentyl Pentyl Pentyl Pentyl Pentyl Pentyl Pentyl Pentyl
C5H11OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Hexanol Hexyl Hexyl Hexyl Hexyl Hexyl Hexyl Hexyl Hexyl
C6H13OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Heptanol Heptyl Heptyl Heptyl Heptyl Heptyl Heptyl Heptyl Heptyl
C7H15OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
e e e e e e
Octanol Octyl Octyl Octyl Octyl Octyl Octyl Octyl Octyl
C8H17OH methanoat ethanoat propanoat Butanoat Pentanoat Hexanoate Heptanoat Octanoate
 e e e e e e

Use this space to make your own notes

5.1.3 Explain the difference in melting point and boiling point caused by straight-chained alkanoic acid and straight-
chained primary alkanol structures
Carboxylic Acids

Carboxylic acids have a higher MP and BP compared to normal similar

sized alkanol and alkanes from which they are derived. This is because
carboxylic acids are able to be involved in 2 hydrogen bonds between
carboxylic acid molecules. Hydrogen bonds are very strong and so they
all carboxylic acids to have a very high melting and boiling point as
more energy is required to break these H bonds

Alkanols

Alkanols have a relatively high MP and BP compared to the alkenes from

which they originate due to the ability of alkanol molecules to be involved
in 1 hydrogen bond between each other in the –OH functional group.
These hydrogen bonds are the strongest intermolecular forces and so
require high amounts of energy to break.

Use this space to make your own notes

5.1.4 Identify esterification as the reaction between an acid and an alkanol and describe, using equations, examples
of esterification

Esterification is the reaction between an alkanol containing the OH functional group and an alkanoic acid containing
the COOH functional group to produce an ester and water. The OH from the alkanol combines with the H from the
COOH to form H2O according to the general equation.
 RCOOH + R’OH RCOOR’ + H2O
Example:

1. O conc. O
|| H2SO4 ||
CH3 – CH2 – CH2 – OH + HO – C – CH3 H2O + CH3 – CH2 – CH2 – O – C – CH3

1 – propanol + ethanoic acid water + propyl ethanoate

𝐻2𝑆𝑂4
2. HCOOH(l) + CH3CH2OH(l) ↔
Common: Formic acid + ethyl alcohol ↔
IUPAC: Methanoic acid + ethanol ↔
HCOOCH2CH3(l) + H2O(l)
𝐻2𝑆𝑂4
ethyl formate + water
𝐻2𝑆𝑂4
ethyl methanoate + water

Use this space to make your own notes

5.1.5 Describe the purpose of using acid in esterification for catalysis

Esterification is actually a very slow reaction which reaches equilibrium.

A concentrated H2SO4 catalyst is actually used to lower the activation energy required for the reaction thereby
increasing the rate of the reaction and allowing equilibrium to be achieved must faster (very helpful for industrial
production of esters).

Also concentrated H2SO4 is a dehydrating agent and in large (usually industrial) quantities removes water from the
products as it has a strong affinity to it. By doing so it is disrupts equilibrium, pushing it right. This is to replace the
removed product and in accordance to Le Chatelier’s principle will favour the forward reaction increasing the yield of
the ester.

Use this space to make your own notes

Questions

1. The boiling point of propanoic acid is higher than the boiling point of the butanol. Explain why? (2 mark)

2. Outline the role of a catalyst and identify the catalyst commonly used in esterification

3. Draw and name the structural components of the products formed through the reaction of propanol with
Heptanoic acid. (3 marks)