Module 5: Equalibrium and Acid Reactions

Chapter 2: Qualitative Equilibrium

The two major drives toward enthalpy (∆ H ) and entropy (∆ S ) will affect whether a reaction is
spontaneous and will react to virtual completion due to Gibbs free energy (∆ G ).

∆ G=∆ H−T ∆ S
Where “T” is the given temperature.

If ∆ G> 0 the reaction will not occur spontaneously, If ∆ G< 0 the reaction will occur spontaneously.
This can be seen through aerobic respiration or the combustion of glucose as ∆ G< 0, however
since photosynthesis is in the opposite direction it needs constant energy intake by the Sun to
catalyse the reaction.

When the ∆ G of a reaction is close to zero the reactants may forms products and the products may
form reactants, hence when both species are present two reactions are occurring at the same time.

Model static and dynamic equilibrium and analyse the differences

between open and closed systems
Chemical systems encompass all chemicals involved in a reaction while any chemical around the
reaction that is not involved in the reaction forms the surroundings. Closed systems are chemical
reactions conducted in a space where matter cannot escape while in Open systems matter can be
added or lost.

In a chemical system physical and chemical changes occur. Physical changes occurs when no new
substances are created but the physical properties of the reactant are changed (e.g. state change).
Chemical changes occur when the atoms of the reactants rearrange to form new products with new
physical and chemical properties

Reversable Reactions: Can react in both directions, from reactants to products (forward reaction)
and products to reactants (Reverse reaction). This is indicated by the double direction arrow (⇋ )E.g.

Reversable reactions occur in reactions with a dynamic equilibrium (where the products may react
back into reactants and when the reaction appears to be complete there is both reactants and
products) as opposed to reactions with a static equilibrium (where the reaction completes when all
reactants convert to products).

Dynamic equilibrium is achieved when the chemical system is in a steady state – constant properties
or a fixed quantity of both reactants and products. In a chemical reaction the reaction will start with
100% reactants where, in a reversable reaction as the concentration of products increase the rate of

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reverse reactions back to reactions increase while as the concentration of reactants decreases the
rate of forward reactions decrease. This dynamic equilibrium is reached when the rate of forward
reactions equals the rates of reverse reactions and although the reaction is still occurring the
concentrations of both the reactant and product are in dynamic equilibrium. This must occur in a
closed system. This dynamic equilibrium is represented by:

Analyse examples of non-equilibrium systems in terms of the effect of

entropy and enthalpy
Combustion
Combustion reactions are both exothermic and toward entropy and will therefore favour the
forward reaction

Photosynthesis
Photosynthesis is no-spontaneous requiring energy input to the forward direction

Investigate the relationship between collision theory and reaction rate in

order to analyse chemical equilibrium reactions
Reversibility can be predicted using Collision theory, the concept that reactions between molecules
only occurs when the collide in the correct orientation and have sufficient energy to break the
chemical bonds, this amount of energy being the activation energy (the difference in enthalpy
between the enthalpy of reactants/ products and the activated complex). This activation energy is
required in both forward and reverse reactions, where the difference in activation energies between
the forward and reverse directions determines the dynamic equilibrium.

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Investigate the effects of temperature, concentration, volume and/or
pressure on a system at equilibrium and explain how Le Chatelier’s
principle can be used to predict such effects
Conditions such as temperature, partial pressure (the pressure exerted by a specific gas in a gas
mixture) or concentration of chemicals, pressure and the volume of the chemical system affect the
equilibrium as rate of forward or reverse reaction is altered. This change in equilibrium can be
predicted by Le Chatelier’s principle: “If a system is in equilibrium, then that system will behave in
such a way as to partially counteract any imposed change”. Using this consider the following points:

1. What change is imposed

2. What is the opposite of that change that the system will do
3. Which reaction is favoured - Either reverse of forward
4. Does equilibrium shift to the left (concentration of reactants in equilibrium) or right
(concentration of products in equilibrium)

Basic Template: If “…” is changed in the system then by Le Chatelier’s principle the system will try
to counteract this change favouring the “forward/reverse” direction shifting the equation to the
“left/right”, thereby increasing the production of “…”

The change is equilibrium can be predicted with all these changes in conditions:

Change in concentration and partial pressure: This entails that if the reactant/product is
increased/decreased the opposite will occur in the equilibrium (e.g. Some product is removed, thus
the rate of forward reaction is favoured because there is relatively more reactants that are reactin g
than products, and the equilibrium will shift to the right meaning more product in the equilibrium).
Partial pressure of gases is dependent on its concentration within a volume of gas, therefore a
change in partial pressure is equivalent to a change in concentration.

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Example: If in the reaction the concentration of iodine ( a reactant) is
increased the forward reaction is favoured and the reaction will go to the right

Changes to Volume and Pressure: Pressure and volume are inversely proportional, ie. If volume of
gas or liquid is increased the molecules will spread out more and the pressure is decreased.
Therefore if volume/pressure is increased/decreased the system will favour the direction of reaction
that does the opposite (e.g. if the volume is increased making the pressure decrease the equilibrium
will favour the reaction direction that increases pressure gradually and reduce the rate of reaction
initially that reduces pressure)

In this case the reverse reaction rate is favoured and the equilibrium shifts to the left producing a
higher concentration of reactants.

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Changes in temperature:

When temperature changes due energy released or taken away in a closed system the reaction will
favour the direction the opposes the heat transfer (i.e. If heat is increased the endothermic direction
of the reaction will be favoured) therefore shifting the equilibrium. This change in equilibrium is not
as sudden as the other changes when graphed.

Example:

Given that energy is released into the closed system the endothermic direction will be favoured and
therefore the dynamic equilibrium will be shifted to the left.

This occurs due to collision theory, the activation energies needed for the reaction to occur in either
direction differs due to the different energies of the reactants and products. If the energy is
increased, both the rate of forward and reverse directions is increased. However, the percentage of
particles able to react in the endothermic direction which requires higher activation energy, is higher
than in the exothermic direction which requires lower activation energy.

If a catalyst is introduced to equilibrium is simply achieved in a quicker amount of time.

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Heating cobalt (II) chloride hexahydrate
This molecule can take two forms; one lower energy and coloured pink, and the other higher energy
and coloured blue, changing between structures in this equation

Given the forward direction is endothermic if the system is heated the forward direction is favoured
to counteract the change in heat shifting the equilibrium to the right and vice versa

Interaction between Nitrogen Dioxide and Dinitrogen tetroxide

Nitrogen Dioxide is a clear, higher energy gas while dinitrogen tetroxide is a dark brown and lower
energy changing between forms by the equation:

Therefore, if heat is increased due to Le Chatelier’s principle will be counteracted by the system and
thus the forward direction is favoured shifting the equilibrium to the left turning the mixture of the
gases slightly clearer. And vice versa.

Also, if the volume is reduced and therefore the pressure increases the system will favour the
direction that produces less pressure. Given that the reverse direction goes from two moles of gas to
one, if the volume was decreased and thus the pressure increased the reaction would favour the
reverse direction and the equilibrium would be shifted to the left.

Chapter 3: Calculating the equilibrium constant

Deduce the equilibrium expression for homogeneous reactions occurring
in a solution
The equilibrium constant ( K eq ) or is the ratio between the concentrations in the products and the
reactants in a specific reaction when the system is in equilibrium. On the other hand, the reaction
quotient (Q) is the ratio between the concentration of products to reactants at any point in the
reaction, as such if Q< K then less products have been produced then in K – the equilibrium and
thus the reaction is not at equilibrium and the forward reaction is favoured to reach equilibrium.
Vice versa when Q> K . When Q = K the reaction is at equilibrium and has completed.

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Perform calculations to find the value of K and concentrations of
substances within an equilibrium system
If this is reaction:

[ products ]
K eq =
[reactants]

K eq =¿ ¿

- The products are in the numerator and reactants in the denominator

- The coefficient of each species is now the power
- The species is replaced by the concentration of the species at dynamic equilibrium (mol L−1)

The size of K indicates how far the reaction has gone, and whether the equilibrium lies to the left or
right:

- If K is large (larger than 1000) then the reaction goes close to completion and the
equilibrium is to the right
- If K is close to 1, then the reaction neither favour the right or left have will have relatively
equal concentrations of reactants and products
- If K is small (less than 0.001) then the reaction occurs to a small extent and the equilibrium is
to the left

Practise question on page 62-71 of textbook

Quantitatively analyse the effect of temperature on the value of the

equilibrium constant
Temperature change due to Le Chatelier’s principle will be counteracted by a system by favouring
the direction of reaction that favours the reverse process thus shifting the equilibrium and changing
the equilibrium constant. Thus, if the heat is increased favouring the reverse endothermic reaction
the equilibrium will be shifted to the left. Given that there is now a higher concentration of reactants
in the denominator and lower products in the numerator of the equilibrium constant the equilibrium
constant will decrease in quantitative value.

Conduct Investigation To determine K eq of iron (III) Thiocyanate

equilibrium

Explore the use of K eq for dissociation of acids and bases and gases: (USE
HSC LABS)
In strong acids or bases the molecule dissociates (meaning an ionic substance splitting into its ions)
in water. However weak acids or bases will only partially ionise or dissociate in water. For example:

This dissociation is reversable and therefore the dissociation reaction will reach a equilibrium with
this equilibrium constant represented as K a , for acids and K b , for bases. In this situation above the
K a is given as:

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 [concentration of dissociated ions]
Ka=
[concentration of acid ]

In reversable gas equations an equilibrium is also reach but instead of concentration the partial
pressure is used (either in atmospheres (atm.), kilopascals (kPa) or millimetres of mercury (mmHg),
as long as all the units are the same). In questions using the moles of a gas measure the gases molar
fraction (mf) or the percentage of that gas amongst others, given as:

number of moles of specified gas

mf =
total number of moles of gas present
Then using this molar fraction calculate the partial pressure (pp) or pressure exerted by one gas inn
a gas mixture which is proportional to the molar fraction and the total pressure of the system, given
as:

pp=mf × pressure of system

Then just use the partial pressure as you would normally to find the gaseous equilibrium constant
denoted as K p

Chapter 4: Solution Equilibria

Dispersion forces are the basic electrostatic attractions between the positive nucleus of one atom
and the electron cloud of another atom. Ionic bonding is formed by a crystalline structure of positive
and negative ions that have electrostatic attractions to form strong intermolecular bonds. Covalent
bonds involve the shared of electron pairs between atoms to form strong intramolecular bonds but
has weak intermolecular bonds. However, if the covalent bond is polar, meaning that the is an
imbalance in the sharing of the electron pair a dipole is produced due to different electronegativities
of the atoms sharing the electron. This dipole forms the relatively strong intermolecular covalent
bonding in water, which involves hydrogen bonding– the intermolecular covalent bonding involving
covalent molecules involving Hydrogen with Fluorine, Oxygen and Nitrogen (FON Bonds) because of
these substances high polarity compared to hydrogen.

Water of Crystallisation occurs when this strong intermolecular dipole force dissolves the ions of
salts overcoming the ionic bonds of the salt positioning water molecules around each ion, hydrating
(completely surrounding the ions with solvent molecules) the ion – ion-dipole bonding. A molecule
in ion-dipole bonding with a metal is known as a ligand which arrange themselves around the metal
ion according to VSEPR theory. If the water is evaporated out of the solution the ions go from being
hydrated to anhydrous.

Describe and analyse the processes involved in the dissolution of ionic

compound in water
Dissolution occurs when a solvent with high polarity (e.g. water) uses this dipole charge to attract to
the anion and cation of a salt, breaking them apart, thereby dissolving the salt. The positive pole of
the dipole of the molecule of the solvent is attracted to the cation. The positive pole of the water
molecules will orientate around the anion until it is perfectly hydrated. Same will occur for the cation

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component of the salt. For an ionic substance to dissolve in water the energy required to separate
the ions must be less than the energy released when the ion becomes hydrated.

Solubility is the mass of solute able to be dissolved in 100g of solvent at a given temperature.
Solubility varies with temperature which can be seen by a solubility graph.

Unsaturated solution: More solute can be dissolved in

Saturated solution: Point at which no more solute can be dissolved in

Supersaturated solution: More solute is within the solvent than in the saturated solution

Investigate the use of solubility equilibria by Aboriginal People when

removing toxicity from cycad fruits
The cycad found in north-eastern Queensland contains high levels of mercury. To detoxify the cycad,
the fruit would be initially cooked, then ground into a meal and then leached. Leaching involves the
soaking of the cycad in a flowing river over several days letting the highly soluble toxins dissolve into
the water leaving behind a now edible cycad.

Conduct investigation to determine solubitlity rules, and predic and

analyse the composition of substances when two ionic solutions are mixed
Aqueous Solutions: Solutions with water as the solvent

When ions dissolve in water the dissociate or separate the degree to which they do is categorised as:

Soluble: Solubility of more than 10 g L−1

Sparingly Soluble: Solubility of 1-10 g L−1

Insoluble: Solubility of less than 1 g L−1

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Precipitation reactions involve the mixing of aqueous solutions to form a solid precipitate. The
spectator ions are the ions in the solution that are not involved in the precipitation reaction.
Precipitation reactions can be written as:

- Neutral species equation: Shows solutions

- Complete ionic equation: Shows ions
- Net ionic equation: Shows ions but not spectator ions

Solubility Table:

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Derive equilibrium for saturated solutions in terms of K sp and other
questions
When a solution becomes saturated the rate at which the ions are dissolving is equal to the rate at
which ions are forming precipitate – reaching a dynamic equilibrium where the equilibrium constant
is known as the solubility product ( K sp ).

If the equation is:

The K sp is equal to the product of the concentrations (mol L−1) of the aqueous ions each to the
power of their coefficient:

K sp =¿

An ionic product (Q sp ) as opposed to a solubility product represents the reaction quotient of the
process from aqueous dissolved ions back toward a solid precipitate. Therefore if:

In questions involving a solubility or ionic product the harder questions will give the gram amount of
either the precipitate or ions. Convert this amount to mol L−1, or molar solubility by using the
m
nm= .
mm
4.8 The Common Ion Effect
The common ion effect occurs when ionic compounds with a common ion (e.g.
2−¿¿
N a2 S O4 and CaS O4 ). So if a saturated solution with dissociated C a2+¿ and S O ¿ ions has been
4

2−¿¿
added with N a2 S O4 there will be an excess in the common ion; being S O 4 ions. Due to Le
2−¿¿
Chatelier’s Principle the system will counteract this change in concentration of S O 4 ions by
favouring the precipitation or reverse reactions of both reactions shifting the solubility equilibrium
to the left.

Since C a2 S O4 is sparingly soluble and N a2 S O4 is a soluble salt the less soluble salt will decrease in
solubility. To do questions involved with this find the initial K sp in water. Then multiply this initial
K sp value with the molar solubility of the added salt using the following expression. Essentially, let
the K sp value in water equal to the molar solubility of the new solution times the solubility value
that needs to be found.

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Module 6: Acid/Base Reactions
Chapter 5
Investigate the correct IUPAC nomenclature and properties of common
inorganic acids and bases
Substance can either be organic or inorganic:

- Inorganic, being derived from a non-living material

- Organic, being carbon-based and are derived from once living matter

Acids and bases can be defined according to their properties and reactions, or the hydrogen ions
+¿¿
attract to the water molecules to form hydronium ions ( H 3 O ).
+¿¿ −¿¿
Svante Arrhenius defined acids ( H ) and bases (OH ) as matter that dissociate in water
releasing ions

Acids can be categorised as:

- Binary Acids: Made up of hydrogen cation(s) and one non-metal anion. They are named
using “hydro”, for hydrogen combined with an abbreviated name for the non-metal (e.g.
chlorine  chlor) with the suffix “ic” (e.g. hydrofluoric acid)
- Oxoacids: Made up of hydrogen cation(s) and an oxoanion (a polyatomic anion compound
comprised of a non-metal bonded with oxygen). In naming no “hydro” is used and the suffix
“ic” is replaced as the suffix for the oxoanion. However, in the example of sulphate and
sulphite, and others where the oxoanion has two different variations with a varying number
of oxygens. The suffix “ate”, belonging to the oxoanion with the greater number of oxygens
turns turns to the regular suffix “ic”. On the other hand, “ite” is replaced with “ous”. In more

complex scenarios, for example with four variations the higher number will have the
oxoanion’s prefix is “per” and the suffix is “ic”. For the second highest just the suffix “ic and

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 for the second lowest just the suffix “ous”. Finally, the oxoanion with the lowest number of
oxygens has the prefix “hypo” and suffix “ous”

Properties of acids
- Acids and bases react in pairs where the acid releases a hydrogen ion, while the base accepts
the hydrogen ion
- When an acid dissociates in water the resultant solution is electrically conductive
- Acids react with many metals, carbonates
- Can be indicated by turning the colour of litmus to red
- Sour taste

Inorganic base nomenclature

Alkaline solutions when bases dissociate in water. Bases accept hydrogen ions and release hydroxide
ions or oxide O 2−¿¿ ions; however, bases may not dissociate in water. Alkali metals and alkaline
earths, the groups in the periodic table are named such as their metal hydroxides give basic, alkaline
solutions. Most other metal hydroxides are not soluble in water. To name this base state the cation,
then the anion with the suffix “ide”.

Properties of Bases
- Dissociated bases in water will create an electrically conductive solution
- Some bases react with reactive metals
- Litmus turns blue
- Bitter taste

Conduct an investigation to demonstrate the preparation and use of

indicators as illustrators of the characteristics and properties of acids and
bases and their reversible reactions
Red Cabbage water
1. Heat a mixture of water and cabbage
2. Using the cabbage water test various acids and bases to determine their pH
3. The brighter pink – the more acidic and the more yellow the more basic. Purple when
neutral

This is because red cabbage contains anthocyanin. A molecule that changes molecular structure
depending on the concentration of hydrogen ions (from acids) and hydroxide ions (from bases) in its
surroundings.

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Predict the products of acid reactions and write balanced equations to
represent:
Acid-base ionic reactions are known as double displacement reactions; being a reaction that starts
and ends with the same number of substances. However, an atom or an ion in one or both
compounds is displaced. E.g.

Acids and bases

In acid-base/neutralisation reaction (acid + base  salt + water). Where the salt is comprised of the
metal of the aid and the non-metal of the base, test if the salt is dissolvable in water to see if it is
aqueous. Most neutralisation reactions go to completion, however the reaction between a weak
acid and a weak base is reversible

Acids and carbonates

Acid-carbonate reactions (acid + carbonate  salt + water + carbon dioxide). Where the salt is
comprised of the calcium metal cation of the carbonate (CO 3), and the non-metal of the acid.

Predict the products of acid reactions and write balanced equations to

represent acids and metals
For an acid to react with a metal the metal must be reactive enough, or willing to donate electron(s)
to the released hydrogen cations from the acids (according to Svante Arrhenius) in order to form
hydrogen gas and a salt (from both the metal ion that donated the electron(s) and the non-metal
anion of the acid). (dilute acid + metal  salt + hydrogen gas). Acid-metal reactions are
displacement reactions as for example:

Because Magnesium displaces the hydrogen. This is because magnesium is more reactive, having a
lower first ionisation energy than hydrogen, meaning it has a higher tendency to lose valence
electrons. Thus, acid-metal reactions mean valence electron transfers from the metal (which is being
reduced) to the oxidised hydrogen. This can be seen by half-equations.

Investigate applications of neutralisation reactions in everyday life and

industrial processes
Neutralisation is the cancelling effect of an acid and a base. This occurs as the hydrogen cation from
the acid and the hydroxide anions from the base, due to Arrhenius’ theory, react to form water.

Neutralisation reactions are used in pools to keep the water at an optimal pH of 7.2-7.8. If the pH
goes above 7.8 algae and bacteria will form, to neutralise this effect Sodium Hydrogen Sulphate

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(NaHSO₄). If the pH falls below 7.2 it will become corrosive for the swimmer, to neutralise this effect
Sodium Carbonate (Na₂CO₃) may be used.

Acid reflux occurs when the oesophageal sphincter is not functioning properly allowing stomach acid
to rise in the oesophagus causing pain. Bases (e.g. Magnesium Hydroxide) can neutralise the acid
rising through and halt acid reflux (particularly HCl).

To determine the concentration of an unknown acid or base titration can be used. This involves
combining the unknown solution with a reagent solution of a known solution – the standard
solution. The two solutions are mixed until the mixture is neutral.

In industrial processes effluent (or liquid waste) is produced which needs to be treated before being
put back into the environment. This is especially important for acidic effluent which must be
neutralised. Additives such as calcium oxide, calcium carbonate, and sodium bicarbonate are added
to neutralise to effluent. These processes are used in:

- electroplating: This is the production of a thin surface of one metal on another using
electrical current.
- beverage industry in the cleaning of reusable bottles
- dairies and meat processing plants
- paper and pulp industries leather and textiles
- laundry and dyeing
- cement and concreting etc.

The effluent can be acidic or basic and have other harmful chemicals such as Chromium or cadmium
−¿ ¿
and cyanide (CN ) are present. Carbon dioxide is used to neutralise basic effluent due to the
Carbonic acid it produces with water and given that carbon dioxide is often a by-product of industrial
processes it can be recycled meaning it is cost effective and safe for the environment. Also, acidic
gases (e.g. carbon, nitrogen and sulphur dioxide and hydrogen sulphide) are hazardous pollutants.
Dry systems such as a Spray dryer Absorber is a desulphurisation process removing oxides from
sulphur. The gas is absorbed onto slaked lime (Ca(OH)2) and a dry powder is formed which can safely
stored. The process follows the formula:

Conduct a practical investigation to measure the enthalpy of

neutralisation
Enthalpy is a measure of the total energy possessed by a substance or group of substances. A
calorimeter can be used to measure the enthalpy change for a neutralisation reaction. A calorimeter
can be made by using an heat insulated cup and lid to ensure a closed system with a temperature
probe placed inside. Record the initial room temperature of 25 ml .1 mol Hydrochloric acid and
Sodium Hydroxide. Them mix the solutions in the calorimeter and record the maximum temperature
that the mixture reaches. From this the change in temperature can be calculated (∆ T ) and with the
specific heat capacity of water 4.18 (C) and the mass of the mixture which is 50 grams (m) the
change in heat (q) can be established using q=mC ∆T . Then the molar change in enthalpy can be
found by finding the amount of moles of the water formed (n) using the acid and bases
concentration (c) and volume (V) in the formula n = cV. Once “n” and q” and found the molar
q
enthalpy change (∆ H ) can be calculated in ∆ H = .
n

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Explore the changes in definitions and models of an acid and a base over
time to explain the limitations of each model, including but not limited to
Antione Lavoisier in 1776 proposed the first theory on acids, that acid contain oxygen based on his
observation that when oxides of non-metals dissolved in water, acidic solutions where produced.
Humphry Davy in 1799 concluded that acids contain hydrogen by electrolysing hydrochloric acid,
observing hydrogen and chlorine gas but no oxygen gas, disproving Lavoisier’s theory. However, he
did not explain why some bases contained hydrogen.

Svante Arrhenius in 1883 proposed that acids and bases formed ions when dissolved in water.
Arrhenius’ theory is that acids increase the concentration of hydrogen cations in water and bases
ionise in water to increase the concentration of hydroxide anions in water and that the more ions
released by the acid/base the more strong the acid/base is. This contributed to the pH scale, which is
the measurement of the concentration of these ions in a solution. However, this theory did not
explain the role of the solvent for the acid and base in the process of the neutralisation reaction and
it excludes metal oxides and carbonates as bases because they do not contain hydroxide. Also, the
Ammonia dilemma, that Ammonia NH 3 despite having properties of a weak acid did not contain
−¿¿
OH , thus not aligning with Arrhenius’ theory. This could be explained for aqueous ammonia as it
reacts with water to produce the hydroxide ion:
−¿¿
+¿+O H ¿
N H 3 + H 2 O=N H 4

However, ammonia gas reacts with hydrochloric acid, a known acid to form one salt. Thus, the
definition of an acid and base must be redefined.

In the early 20th century Johannes Bronsted and Thomas Lowry independently proposed the same
+¿¿
theory, now known as the Bronsted-Lowry Theory which states that acids are proton or H donors
+¿¿
and bases are mere proton or H accepters rather than substances that need to release hydroxide
or oxide anion. The theory required the simultaneous transfer and acceptance of protons. That is for
a substance to behave like an acid, there must be a base.

This theory also explains ammonia as a base and the role of solvents in neutralisation reactions. In
the neutralisation equation:

+¿¿
This equation is explained as ammonia N H 3, accepts the proton to form the cation N H 4 and is
thus acting like a base under the definition of a proton acceptor, whilst the HCl is acting as an acid
−¿¿
donating the proton to form Cl .

Similarly, when HCl reacts with water, HCl is acting as an acid donating the proton and the water is
+¿¿
acting as a base accepting that proton to form a hydronium ion ( H 3 O ). However, water can also
−¿¿
+¿+O H ¿
act as an acid in the equation: N H 3 + H 2 O ⇆ N H 4 . To be able to act as both an acid and a
base in the broader Lewis model is to be amphoteric while amphiprotic molecules are able to
donate and receive hydrogen ions, thus acting as both an acid and base by the Bronsted-Lowry
definition. However, this model only explained acid base reactions in an aqueous solution, as for a
substance to be called an acid a hydrogen ion must be transferred via a solvent. It also cannot
explain why some known acid do not contain hydrogen. Finally, it cannot explain the reactions
between acidic oxides and basic oxides (e.g. ). This is a table regarding

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acidic, basic and amphoteric oxides but the general rule is metal oxides are basic and non-metal
oxides are acidic:

The Lewis model does not require a proton or solvent merely stating that an acid is any atom or
molecule that can accept electrons, while a Lewi base is any atom or molecule capable of donating
electrons. Thus, no solvent is needed. Also, it explains why molecules without hydrogen like B F 3
react with the base N H 3. This is because the Boron acts as a Lewis acid accepting the non-bonding
electron pair of the ammonia, or which donates the electron pair thus being a Lewis base, forming
the salt B F 3 N H 3 .

Chapter 6: Using Brønsted-Lowry theory

+¿¿ +¿¿
The Brønsted-Lowry theory characterises acids as H donors, and bases as H recievers. Thus, a
standard neutralisation reaction can be written as:

+¿¿ −¿¿
In the forward reaction HA donates a H making HA an acid and reacts to produce into A . B
+¿¿ + ¿¿
accepts the H making it a base which reacts to produce H B . However, reaction what the base
+ ¿¿ +¿¿ −¿¿
“B” produced; being H B in the reverse reaction is an acid as it donates a H to A . Thus, the
−¿¿
pair of HA being A is a base. Thus, a molecule that acts as an acid in the reactant side acts will
+¿¿
lose a H , turning into a base on the product side and vice versa. These acid-base pairs are called a
+¿¿ −¿¿
conjugate pair and differ by one proton H . In this example A is the conjugate base of HA and
−¿¿
HA is the conjugate acid of A . E.g.

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For monoprotic molecules, strong acids ionise to produce weak bases, while weak acids ionise to
produce strong bases.

Conduct a practical investigation to measure the pH of a range of acids

and bases
Universal indicator can be used to observe the pH of a sample. It is composed of 4 ingredients:
Thymol blue, Methyl red, Bromothymol blue and Phenolphthalein. However, since adding the
indicator will contaminate the sample, this is a destructive method to detect pH and is qualitative
and thus subjective. A non-destructive method is a pH probe which detects the voltage of a solution
relative to the voltage of a standard solution (pH of 7) to determine the solutions pH.

Calculate pH, pOH, hydrogen ion concentration ([H+]) and hydroxide ion
concentration ([OH–]) for a range of solutions (ACSCH102)
The pH scale is a numerical scale generally from 0-14, and measures the concentration of hydrogen
+¿¿
ions ([ H ]) in a solution. Since these hydrogen ions attach to water molecules to form hydronium,
the scale is more accurately based on the concentration of hydronium ions (for example if pH is
−n
n the concentration of hydrogen ions is10 )
Thus, pH=−log 10 ¿ ¿ (page 151 has questions on this topic)

Note: When deciding the amount of decimal places for the pH value using the same number of
significant figures (e.g. 0.042M – 2 significant figures) to get pH =−log 10 [0.042] , and write the
final answer as pH = 1.38 – 2 decimal places.

pH is also dependent on temperature and pressure, where at standard conditions (at 25 degrees
celcius) the neutral pH is 7. This measurement of hydrogen ions corresponds with the number of
hydroxide ions as seen by:

This scale for the measurement of hydroxide ions is considered the pOH scale. To convert pH to pOH
or vice versa use the formula pH + pOH = 14.

18 | P a g e
Conduct an investigation to demonstrate the use of pH to indicate the
differences between the strength of acids and bases (ACSCH102)
Concentration of an acid or base is indicated by pH, being the concentration of hydrogen ions in a
solution. However, strength is the degrees to which an acid or base will ionise in water, with strong
acids and bases completely ionising in water with the reaction going to completion (
−¿¿
+¿+ A(strong ) ¿
H A ( strong )+ H 2 O⟶ H 3 O ), while weak acids/bases ionise partially in water, being a
−¿¿
+ ¿+ A (weak) ¿
reversable reaction ( H A ( weak )+ H 2 O ⇌ H 3 O ). Therefore, the degree of the strength of an
acid/base determines what percentage of the acid/base will ionise and thus the concentration of
hydronium ions or hydroxide ions in the solution. To figure out the pH of a weak acid simply find the
pH of the acid if it were to completely ionise, then state that the pH is less acidic or basic than that
value. For example:

Monoprotic acids: Acids that release only one proton per molecule when they ionise (e.g. HCl,
HN O3 ). While, diprotic acids ionise to release 2 protons, triprotic acids release 3 and polyprotic
acids release more than 1 proton per molecule (e.g. H 2 S O 4 or H 3 P O 3). When given the molar
concentration of these acids you must find the ration between the number of acid molecules to
number of hydronium ions produced in order to figure out the pH.

To test for this syllabus point use page 158

Water is amphiprotic, and thus can react with itself to form both hydronium and hydroxide ions. This
is the self-ionisation of water:

This is a reversable reaction and the forward direction occurs to a very small extent so the
equilibrium constant or the self-ionisation constant K w is very low at a known value of 1.0 ×10−14:

19 | P a g e
This entails that in water the concentration of both hydroxide and hydronium ions is 10−7 mol L−1.
Thus, to determine whether an aqueous solution is acidic, alkaline or neutral the solutions
concentration determines pH.

When the concentration or volume of the acid or base change use the formula c 1 V 1=c 2 V 2. This
formula can be used as if water solvent added or removed (evaporated) the amount of hydronium or
hydroxide ions remains constant and thus the concentration is altered.

To determine the equilibrium constant of the ionisation reaction of a weak acid (or base) or K a for:

Use:

You may notice that the concentration of H 2 O has not been accounted for. This is because it is
occurring in an aqueous solution and there is always and excess of water.

Percentage ionisation is the percentage of the acid/base that ionises in water and can be

determined by in the equation :

[concentration of the conjacate base produced ]

%= or %=¿ ¿
[concentration of acid at the beginning of ionisation]
Questions on page 160-171

The K a of polyprotic acids for each donated hydrogen cation. The first ionisation constant, where
the first hydrogen is donated is given by K a 1, and each subsequent ionisation is given K a 2, K a 3 , and

20 | P a g e
so on. Generally the first ionisation constant is largest and will decrease for each subsequent
ionisation of the acid. This is occurs in both strong and weak polyprotic acids:

- Strong polyprotic acids: For example; H 2 S O 4 will first release one proton in the equation
with a defined K a and since H 2 S O 4 is a strong acid it will completely ionise:

−¿¿
Now HS O4 the conjugate base of the original H 2 S O 4 has to react as an acid with other
−¿¿
water molecules to donate its second proton. However, HS O4 and all other conjugate
bases of polyprotic acids after their first hydrogen donation are weaker acids and thus the
subsequent K a value, in this case K a 2 is considerably less than K a 1 as seen by:

- Weak polyprotic acids: (e.g. sulphurous acid H 2 S O 3 ) occurs the same way except with even
smaller K a values.

For a numerical scale of K a , p K a can be found the same way as pH or pOH by:

p K a=−log 10 [K a ]

pH can also be found with both the p K a and percentage ionisation in the formula:

Note: The same principles apply to bases ( K b ) as acids and K a .

Questions 170-176

pH of salts
Even when an acid and base neutralise reaching an equivalence point (when the reactants are in the
molar ratio as shown in their balanced chemical formula and the reaction has gone to completion)
the remaining solution is not neutral if either the base and/or the acid is weak. This is because a
weak acid produces a conjugate base that has basic properties and a weak base produces a
conjugate acid that has acidic properties. On the other hand, strong acids/bases conjugates are
neutral. This means that if the salt produced is soluble, the conjugate acid and base ions forming the
+¿¿
salt will dissociate so that the conjugate acid/base can react with water to produce either H 3 O or
−¿¿
OH respectively, thus changing the pH of the solution. Generally, the weaker the acid or base
the stronger the conjugate will be. When both conjugates in the slat are weak, which ever conjugate
has a higher K a or K b with water will determine whether the final solution is acidic or basic (if
K a > K b the solution is acidic, while if K a < K b the solution is basic).
−¿¿ −¿ ¿
Some conjugates such as HC O3 or H 2 P O 4 are amphiprotic are thus will react as both an acid
and a basic to varying degrees. This is because they are conjugate bases of weak acids, and therefore
are weak bases, but they were also originally the conjugate bases of polyprotic acids and therefore

21 | P a g e
can also donate protons, thus acting as an acid. The K a and K b can be compared to determine
whether the conjugate is has more of an acidic or basic effect on the solution. For example, for
−¿¿
HC O3 :

−¿¿
Given K a > K b, the conjugate ion HC O3 has a acidic effect on the solution

Chapter 7: Using quantitative analysis

Titration is the main method of volumetric analysis (analysis degerming the concentration of a
sample of a given volume of solution by finding the equivalence point it creates with another
solution of known concentration and volume) that can determine the equivalence point of a
neutralisation reaction, at this point an end point (the physical sign that indicates that the
equivalence point has been reached) can be determined using an indicator. It attempts to measure
the concentration of the analyte – or unknown solution. The specialised glassware used for
volumetric analysis are as follows:

- Pipette: Measures a fixed amount of solution which it will dispense. The solution that is
dispensed is known as the aliquot. Before use the pipette must be rinsed once with distilled
water and then three times with the given solution. Uncertainty: ± .03 mL

- Burette: Allows the measurement of the exact volume of the solution in the burette – the
titrant, needed to be added to the other solution to reach the equivalence point. Same
rinsing method as pipette except also opening the air lock so that the air lock is also rinsed.
Uncertainty: ± .02 mL

- Volumetric Flask: Used for accurately diluting solution to a given volume making a primary
standard solution, as shown by the line of the flask. Must only be rinsed with water as any
added solution with effect number of moles of the acid/base in the final solution.
Uncertainty: ± .03 mL

To make the procedure more accurate by removing the systematic error of relatively low accuracy
glassware measuring cylinders (± .3 mL) and graduated beakers (± 5 mL)

22 | P a g e
As mentioned the equivalence point my not be when the solution is neutral because of the salt
produced. To find end point of the following solutions these indicators can be used:

- Equivalence point with neutral salt: bromothymol blue (range: 6.2 – 7.6 or yellow – blue)
when it turns green
- Equivalence point with acidic salt: methyl orange (range: 3.1 - 4.4 or red – yellow) whenx
it turns red
- Equivalence point with basic salt: phenolphthalein (range: 8.3 – 10 or colourless – pink)
when it turns pink

To accurately determine the concentration of an unknown solution it is titrated against a solution

that is accurately known – the primary standard which must be stable under laboratory conditions
as well as:

- Have a high molar mass, so that the percentage of error is lower

- Be affordable
- Be pure, so that no side reactions occur
- Not react with air or have any water of hydration (ie. React with water)
- Dissolve readily in solvent

Primary Standard Acid: Oxalic acid (COOHCOOH )

Primary Standard Base: Anhydrous Sodium Carbonate ( Na2 C O3 )

More common acids and bases such as hydrochloric and sulfuric acid and sodium hydroxide are not
used as primary standards as their concentrations vary from batch to batch and are hard to obtain in
their pure form as they may react with water and carbon dioxide.

Conduct practical investigations to analyse the concentration of an

unknown acid or base by titration
Basic standard solution method:

- Weigh an amount of the substance that corresponds with a molar value in a beaker
- Dissolve, using a stirring rod the substance in a small volume of distilled water (e.g. 100 mL)
until the substance has completely dissolved
- Pour the solution in a volumetric flask of a given volume greater than the volume of the
current solution (e.g. 250 mL). Rinse the beaker and stirring rod multiple times with distilled
water transferring the rinse to the flask in order the transfer all the substance into the flask.

23 | P a g e
 - Add distilled water into the flask until the bottom of the meniscus reaches the graduation
point of the volumetric flask
- Place a stopper on the volumetric flask and invert the volumetric flask multiple times to
thoroughly mix the solution

Basic titration method:

1. Fill the burette with the titrant, usually an acid (since caustic bases can damage the fine
glassware)
2. Pour using a pipette the known volume of the other solution the analyte, in a conical flask
adding two drops of the chosen indicator
3. Slowly add the solution in the burette until the end point is reached noting the volume of
solution that has transferred from the burette into the solution
4. Repeat the experiment several times until the solution added from the burette is consistent
to within ±1 mL and average the titrant volume for all consistent results removing outliers
5. Write a balanced chemical equation and determine the concentration of the unknown
solution

Safety Table:

Identify Risk Severity of Risk Precaution

Chemicals coming in contact High Wear safety glasses and a
with skin or eyes protective clothing throughout
the duration of the titration
Glassware breaking in hands High Handle the glassware with
care and wear protective
rubber gloves when handling
the glassware

Note: Add any relevant cleaning information about the glassware to the method, as well as parallax
and instrumental error.

Investigate titration curves and conductivity graphs to analyse data to

indicate characteristic reaction profiles
Titration curves measure the relationship between the pH of a solution undergoing titration and mL
of titrant added. This form of titration uses a pH probe instead of an indicator where the equivalence
point is indicated by a mid-point on the near vertical change on the graph. Graphs differ for:

Strong acid – Strong base:

Strong acid – Weak base:

24 | P a g e
Weak acid – Strong base:

Model neutralisation of strong and weak acids and bases using a variety of
media
Also, conductivity can indicate an equivalence point if a conductivity probe is used for the titration –
conductometric titration. This is because ions can conduct electricity, where the lighter the ion the
greater its conductivity. The equivalence point is indicated by a sudden change in conductivity and is
different for different reactions:

Strong acid – Strong Base: For example; in the reaction H Cl(aq) + NaOH (aq) ⟶ NaCl( aq) + H 2 O (l).
As evident the reactant side has ions which are lighter an have greater conductivity relative to the
−¿¿
ions in the products because of the light and thus, conductive H +¿ and OH ¿ ions. Therefore, when the
molar ratio is reached and there are only products in the solution the solution’s conductivity is at a
minimum. If the titrant that is being added is NaOH and the aliquot is HCl there will be and excess of
+¿¿
H ions at the start of the titration meaning a high conductivity which would be gradually
+¿¿
decreased to a minimum as the H ions react to produce water. After the molar ratio is reached
−¿¿
the conductivity then increases because of an excess in OH ions.

25 | P a g e
Strong acid – Weak base: When a weak base e.g. N H 3, is added to a strong acid e.g. HCl, the
conductivity decreases until the equivalence point is reached and the conductivity almost plateaus.
+¿¿
This is because although the strong acid, HCl is in excess with highly conductive H ions after the
equivalence point is reached the weak base, N H 3, doesn’t ionise in water or conduct to any
appreciable extent.

Weak acid – Strong base: When a weak acid is titrated with a strong base the equivalence point is
shown by a curve in the graph (e.g. acetic acid and sodium hydroxide). The graphs starts with a low
+¿¿
conduciveness as the weak acid doesn’t ionise that well, resulting is a low concentration of H
+¿¿
ions. The strong base in added and the H ions react with hydroxide ions to form non conductive
water slightly reducing the solution’s conductivity. This slight decrease is due to an increased
presence of the weak acids conjugate base that suppresses the ionisation of the weak acid due to
the common ion effect. For example:

−¿ ¿
By Le Chatelier’s principle by increasing the concentration of C H 3 CO O when the acetic acid
and sodium hydroxide neutralise, the system will counteract the change and therefore favour the
reverse reaction, thus meaning the ionisation of C H 3 COOH will slow down. However when the
graph starts to be linear rather the curved the equivalence point has be reached as the NaOH is in
excess.

26 | P a g e
Weak acid – Weak base:

Another titration form is a back titration where a known excess of a solution neutralises the sample.
Then the solution that is in excess in titrated against another standard solution the determine how
many moles of the excess standard solution was used in that reaction. This can be done for samples
that:

- React to slowly
- Aren’t soluble
- Toxic or volatile

e.g.

Conduct a practical investigation to prepare a buffer and demonstrate its

properties
A buffer is a solution of a weak acid and its conjugate base (or vice versa for bases) that is able to
resist a change in pH when an acid or base is added. It achieves this due to the equilibrium it
+ ¿¿
establishes by Le Chatelier’s principle with the weak acid and conjugate base HA ⇌ A−¿+H ¿. When
an acid or base is added the equilibrium will shift to counteract the addition and the concentration
of hydronium ions returns close to the original concentration and therefore the pH is constant. For
example if a strong acid is added to a buffer the increase in concentration of hydronium ions will be
counteracted by the system and cause the buffer to favour the reverse direction push the

27 | P a g e
equilibrium of the buffer reaction to the left and causing the amount of hydronium ions in solution
to be counteracted to nearer the original value.

Buffer capacity is the extent the amount of acid or base that can be added without a significant
change in pH. This can be increased by having equal parts weak acid and conjugate base as it will be
able to counteract both acids and bases as well as increasing the actual amount of both the weak
acid and strong base.

Add how to make a buffer

Describe the importance of buffers in:

Natural systems
The rising levels of carbon dioxide, calcium and magnesium in oceans may release to much
hydronium in the ocean and change its pH. The natural buffer of the weak acid bicarbonate ( +¿ ¿
¿
−¿¿ −¿+ H O ⇌ CO
2−¿+ H 3 O
¿
HC O3 ) and its basic conjugate base carbonate (C O2−¿¿
3 ) in the equation HC O3 2 3
.
Thus, when an acid increases the concentration of hydronium ions the buffer solution by Le
Chatelier’s principle will counteract this change be favouring the reverse direction, shifting the
equilibrium to the right, decreasing the products and thereby decreasing the amount of hydronium
ions in solution having a buffering effect and returning the pH of the ocean to close to its original
value of between 8.0-8.3 pH.

Biological systems
Using the weak acid carbonic acid and its conjugate base bicarbonate as a buffer to keep the pH of
human blood in between 7.35-7.45. If the pH goes below – acidosis, but if the pH goes above –
alkalosis. If the blood is too basic the forward reaction occurs, and if the blood becomes too acidic
+¿ ¿
−¿+ H O ¿
the reverse direction occurs for the buffering equation H 2 C O3+ H 2 O ⇌ HC O3 3
. The effect
of acids can further be buffered by breathing out the C O2 that is used to make H 2 C O3.

Explore acid/base analysis techniques that are applied:

In industries (2 examples)
pH can be measured by a pH probe or a high pressure liquid chromatography (HPLC)

Wine Industry
The level of acidity affects the taste of wine. Wine is composed of three main organic acids; tartaric
acid, malic acid and citric acid, of which their concentration can be analysed using titrating a sample
of the wine using a strong base such as sodium hydroxide as well as phenolphthalein as an indicator.
The amount of acid is known as titratable acidity. An auto titrator or HPLC can also be used to
determine the quantity of these acids which determine the flavour of the wine.

Juice industry
Juice is titrated to determine the titratable acidity of the juice by titrating a centrifuged sample of
the juice against a strong acid with a phenolphthalein indicator. The main acid is juice is citric but
also tartaric, malic, benzoic and succinic acids. Alternatively, and more effectively HPLC can be used.

By Aboriginal and Torres Strait Islander Peoples

Demonstrated a knowledge of the observable chemical properties of the native flora through:

- Soap: Used leaves and roots of soap tree as an antiseptic cleanser and pain relief. This is
because of the acids within the leaves including saponin (versatile solvent like ethanol), and
methyl salicylate (pain relief)

28 | P a g e
 - Treating stings: Aboriginals used flora (e.g. grey mangrove and goats foot) to treat stings as
they contained alkaloids (basic compounds derived from amino acids)
- Clay/ochre: Clay has alkaline properties and was used to neutralise stomach acid for
heartburn. It was also used as food preservative due to presence of kaolin and was applied
directly to skin to remove skin oils and toxins.

Module 7: Organic Chemistry

Chapter 8: Hydrocarbons
Organic compounds are compounds containing Carbon. Carbon forms four covalent bonds, where if
they are singular bonds will form in a tetrahedral orientation (109.5° between each bond/electron
pair). Carbon may also have double or tripe bonds which change the structural orientation of the
molecule:

Hydrocarbons are compounds made of only carbon and hydrogen. Aromatic hydrocarbons are
hydrocarbons containing one or more benzene ring (cyclohexane) while Aliphatic compounds
comprise of all other hydrocarbons.

Hydrocarbons that don’t form rings; alicyclic, Hydrocarbons that do form rings; cyclic.

A molecular formula (e.g. C 3 H 8 ) only shows what, and how many elements make up the molecule.
Structural formulas also show the structure of the molecule, being either a expanded formula
(shows each atoms arrangement), a condensed formula (condenses the expanded formula into alkyl
groups) or a skeletal formula shows simply the carbon chain arrangement. E.g.

The longest chain of carbon is given the prefix:

29 | P a g e
 No. of Carbons in longest chain Prefix
1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
Substituent chains branching off the main chain are referred to in alphabetical order. These are
known as alkyl groups, they are stated without a “space” before the main carbon chain, and instead
of having the suffix ane, ene or yne, they have the suffix “yl” unlike the main chain but do use the
same prefixes above (e.g. methyl, butyl, ethyl). If there are multiple of the same alkyl group it is
given another prefix; “dimethyl” (two methyls), “trimethyl” (three methyls), “tetramethyl” (four
methyls), “pentamethyl” (five methyls) etc. Before the alkyl group(s) is stated a number is used to
indicate which carbon on the main chain the alkyl group is attached to (e.g. 2,3-diethyl, or 1-methyl).
Since the numbers can be counted from either side of the straight chain of carbons, use the lowest
numbers you can use.

Lets look at this example:

The main chain has 6 carbons attached and is an alkane; hexane

There are 2 methyl groups attached at carbon 2 and carbon 4; 2,4-dimethyl

There is 1 ethyl group attached to carbon 3; 3-ethyl

Since, ethyl, “e”, comes before methyl, “m” in the alphabet 3-ethyl will be stated before 2,4-diethyl

Also, the numbers were counted from right to left to give the alkyl groups the lowest possible
arrangement of numbers.

All the known, the name of this compound is 3-ethyl-2,4-diethylhexane

The whereabouts of this double or triple bond is indicated by the number in between the suffix for
the main chain and the functional group. For example if there is a double bond between carbon 2
and carbon 3 of a carbon chain of 8, the number will indicate the lowest number participating in the
double bond and the name of the compound will read thus; oct-2-ene. Also, since the numbers can
be counted from either side of the straight chain of carbons name it so that it has the lowest number
(this takes priority over alkyl group numbering).

30 | P a g e
Investigate the nomenclature of organic chemicals, up to C8, using IUPAC
conventions, including simple methyl and ethyl branched chains,
including:
Hydrocarbons can be categorised into homologous series. Homologous series is a group of
compounds with similar chemical structures (functional groups) and properties and the same
molecular formula. These are the homologous series below.

Alkanes
Hydrocarbon compound containing only carbon-carbon single bonds – saturated compound,
because they have the maximum amount of hydrogen atoms bonded to each carbon atom. For this
functional group the suffix is “ane”. The generic formula C n C 2 n+2

Alkenes
Hydrocarbon containing at least one double carbon-carbon bond – unsaturated compound. For this
functional group the suffix is “ene”. The generic formula C n C 2 n

Alkynes
Also unsaturated, contains at least one triple carbon-carbon bond. For this functional group the
suffix is “yne”. The generic formula C n C 2 n−2.

The “ene” is given number priority over the “yne” and is said first (e.g. hept-2-ene-5-yne)

Alcohols
Alkanols contain the hydroxyl group OH attached to a carbon atom. To add in a hydroxyl group use
the suffix “ol” after the “ane”, “ene” or “yne” (e.g. Methane  Methanol). It is given the lowest
possible number having higher priority that alkyl groups and “ene” or “yne” bonds(e.g. Propan-1-ol).
Primary alcohols have hydroxyl groups attached to a carbon that is only attached to one other
carbon. Secondary alcohols have hydroxyl groups attached to a carbon that is attached to two other
carbons and Tertiary alcohols for 3.

Aldehydes and Ketones

Aldehydes contain the function group carbonyl; of a carbon atom double bonded to a oxygen atom
and single bonded to a hydrogen:

31 | P a g e
These only occur at the end of a chain and will always get the carbon number 1, hence, they do not
need to be numbered as the only number they get obtain is a one, the rest of the carbons are then
named subsequentially. They have the suffix “al” (e.g. propanal)

Ketones contain the functional group of a carbon atom that is not on the edge of the carbon chain,
double bonded to an oxygen:

The ketone suffix in “one” and it is given the highest numbering priority.

Carboxylic acids
Contains the carboxylic acid functional group

It can only be on the end of a chain and has the suffix “oic” followed by “acid”. E.g. methanoic acid.

Amines and amides

Amines contain the functional group of a nitrogen attached to one (primary), two (secondary) or
three (tertiary) carbon atoms.

The suffix is “amine”. When there is an amine functional group the carbon branches that go off the
nitrogen name the main chain and then the rest as alkyl group attached to N (e.g. N-dimethylbutan-
2-amine).

Amides have the functional group being:

The suffix “amide” is used. To name these name as if it where the main chain, the chain of carbons
attatched to the carbon that is double bonded with the oxygen. Then, if there are alkyl group
attached to the nitrogen, refer to these as a locant of N. E.g.

32 | P a g e
N,N-Dimethylbutanamide

Halogenated organic compounds

These are organic compounds where a halogen (group 17) has taken the place of one of the
hydrogens attached to a hydrogen. These halogens are named the same as to alkyl groups, same
priority for numbering, also named before main chain, are named alphabetically with other halogens
and alkyl groups. Their names are given as follows; fluorine (“-fluoro”), chlorine (“-chloro”), iodine
(“-iodo”) etc. For example;

5 carbons in main chain, Double bond at carbon 1, methyl group at carbon 2, one chlorine at carbon
1 and two chlorines at carbon 4: 1,4,4-trichloro-2-methylpent-1-ene.

Explore and Distinguish the different types of structural isomers, including

chain isomers, position isomers and functional group isomers
Compounds with the same molecular formulas (what, and how many of each element), but different
structural formulas are known as structural isomers. These may be positional isomers, which
change the position of their functional groups or double/triple bond(s). E.g.

Or may be chain isomers which rearrange the molecules carbon skeleton. E.g.

Or may be a functional group isomer, whereby the compound has the same molecular formula but a
different functional group. E.g.

33 | P a g e
Chapter 9: Functional Group Compounds
Construct models, identify the functional group, and write structural and
molecular formulae for homologous series of organic chemical
compounds, up to c8 of alkanes, alkenes and alkynes:
They more bonds between two carbons the greater the intramolecular bonds strength (ie.
Single<Double<Triple) but are more reactive.

Homologous Series: Organic compounds that have the same general formula and whose sequential
members (e.g. methane (C H 4), ethane (C 2 H 6 ), propane (C 3 H 8 )) differ by a C H 2 unit. Alkanes,
alkenes and alkynes are all homologous series as they follow this rule, thus each homologous series
will have the above mentioned chemical properties.

Physical properties like melting and boiling point generally increase by an increase in the number of
carbons in the chain.

Conduct an investigation to compare the properties of organic chemical

compounds within a homologous series, and explain these differences in
terms of bonding and Explain the properties within and between the
homologous series of alkanes with reference to the intermolecular and
intramolecular bonding present
Hydrocarbons are non-polar covalent bonds and thus the intermolecular forces that bind them
together are weak dispersion forces. The structure of the bonding will affect the strength of these
dispersion forces, and thus the compounds melting/boiling point, volatility and flash point.

Only a small amount of energy is required to break the dispersion bonds and thus boil/melt
hydrocarbons. Double and triple bonds reduce dispersion forces, lowering melting/boiling point
slightly. Adding carbons in the chain increases dispersion strength due to the increased surface area
between molecules. Volatility or the readiness of a substance to vapourise at room temp is closely
linked with the melting/boiling point of a hydrocarbon. The flash point of a hydrocarbon in the
minimum temp at which the vapour pressure is high enough to form a combustible mixture with air.
Flash point is linked to the intramolecular forces within the hydrocarbon, thus, as the chain length
increases the temp needed to overcome the intermolecular bonds increases, so too the flash point.

Due to the flash points of hydrocarbons, therefore these safety measures should be implemented:

34 | P a g e
Australia’s National Environmental Protection Measure (NEPM) provides measures for the disposal
of these organic compounds including recycling or treating the waste to form new, useful substances
from non-halogenated waste and burial in a landfill or incineration for halogenated waste. Organic
compounds shouldn’t be poured down the drain as they are generally non-polar, meaning that their
dispersion bonds are not broken down by the dipole-dipole bonds of water, and are thus immiscible,
meaning that disposal in waterways would incur serious damage to aquatic life. They break down
plastic with dispersion so should be stored in glass.

Analyse the shape of molecules formed between carbon atoms when a

single, double or triple bond is formed between them

The Valence Bond Theory can explain bonding shapes based on atomic orbitals. This states that
between two atoms there is a region of space where orbitals each containing an unpaired electron
from each atom overlap. This results in a bonding orbital between the two atoms. A sigma bond is
formed when 2s or 2p or 1s and 1p orbitals overlap along the same axis.

35 | P a g e
Whereas, a pi bond forms when two p orbitals overlap in a sideways manner:

The amount of overlap is less in a pi bond, thus a sigma bond is stronger. Thus, a single covalent
bond – which is a sigma bond is the strongest. A double bond is made up of one sigma and one pi
bond, where the pi bond makes the molecule more reactive than the single bond. A triple bond is
formed by one sigma and two pi, and is thus less reactive than the double bond but more reactive
than the single bond.

Hybridisation refers to mixing atomic orbitals as atoms approach each other. This results in the
formation of hybrid orbitals which are different in shape and energy than the original atoms with its
original orbitals. From this, hybridisations shows the relationship between the geometry of the
atomic structure and the orbitals of the bonding electrons. Carbon forms four covalent bonds must
be

Examine the environmental, economic and sociocultural implications of

obtaining and using hydrocarbons from the Earth
Production and disposal of these hydrocarbons has not only resulted in the depletion of this non-
renewable resource but also a build up of non-biodegradable polymers in landfills. Replacements
such as biomass are a renewable, biodegradable alternative. Natural gas, composed of mainly
methane, but also ethane, propane and butane is valuable as a fuel due to its low flash point. This
gas and other oils are naturally stored by a cap rock in a permeable layer of rock such as sandstone
and can be extracted by fuel wells – these comprise of conventional petroleum. Non-conventional
petroleum is considered to be not environmentally or economically justified sources of fuel such as:

- Deep gas: deep underground and is too expensive to extract

- Shale gas: extracted using fracking which creates toxic waste, can cause earth tremors and
uses excessive amount of water
- Tight gas: gas trapped under impermeable rock and requires fracking as well as acidising
making it very expensive. Acidsing, which involves use of an acid to break down the rock, this
can alter the natural pH of the environment, which would harm the tentative ecosystem as
well as corrode steel and marble buildings in the surrounding area
- Coal seam gas: Requires fracking. Is prevalent in NSW with 30% of natural gas coming from
this form. The fracking process is not as destructive as other forms with government policies
including not to extract CSG with 2 km of existing or future residential areas.

There are also sociocultural implications for crude oil extraction. For example, in ancient times areas
where natural gas naturally flowed to the surface were considered to have supernatural powers. For
example, in Greece, near the town of Delphi with a natural gas seep where the Oracle of Delphi
resided.

36 | P a g e
Through oil spills and other accidents involving hydrocarbons severe environmental and
sociocultural issues arise. The oil slick in the Gulf of Mexico and Hurricane Ivan hit in 2004. Coastal
towns were hit, causing community frustration, unemployment, loss of tourism and severe wildlife
loss. Problems involving transportation of crude oil also arise, causing marine accidents. Oil spills,
such as Exxon Valdez spill of 1989 spilt 41 million litres of oil contaminating 1800 km of coastline,
killing 4 humans and 1000’s of marine and bird life. Economically, 26000 tourist industry jobs were
lost, 10000 fishing jobs were lost or affected combining to a $2.6 billion dollar income loss. This
significantly strained local communities with the economic burden on families likely resulting in
lower education rates and higher crime activity due to lack of jobs, effects that would be felt
intergenerationally.

Chapter 10: Hydrocarbon reactions

Investigate, write equations and construct models to represent the
reactions of unsaturated hydrocarbons when added to a range of
chemicals, including but not limited to:
An addition reaction is a reaction where atoms are added to a hydrocarbon (usually “ene” or “yne”)
because they are attracted to the electron rich area of the hydrocarbon where the double or triple
bond is. The sigma bond of the double/ triple bond is strong but the electrons in a pi bond are more
free to move around and are susceptible to being attacked by electrophiles (a molecule attracted to
electron rich areas of a molecule). An electrophile with two atoms that shares an electron pair will
have its electron pair repulsed by the electron rich double/triple bond of the hydrocarbon creating a
polarity within the electrophile.

The sigma positive atom of the molecule with then be attracted be the negatively charges electron
rich area. This causes that slightly positive atom to separate in its covalent bonding to share an
electron pair with one of the electron pair of the double of triple bond of the hydrocarbon leaving its
covalent partner atom with both their electron pair, making it negative and the other carbon atom in
the double/triple bond missing an electron, making it positive. Thus, these two species will attract
each other and bond covalently as well.

37 | P a g e
This is the formulaic representation of this:

Hydrogen (H2)
The addition of a hydrogen molecule to an alkene or alkyne is known as hydrogenation. The reaction
requires a metal catalyst such as nickel, platinum, palladium or rhodium. To identify this catalyst in
the reaction, do this (e.g. for platinum):

Hydrogenation occurs in 3 steps:

1. The hydrogen molecule attaches to the metal catalyst and break up into molecules
2. Then the alkene attaches to the metal with the hydrogen and the double bond breaks
3. The hydrogen atoms then react with the broken down alkene to hydrogenate the substance

Halogens (X2)
Halogenation is the same as hydrogenation but for halogen molecules

Hydrogen halides (HX)

When hydrogen halides are added across an alkene (e.g. HCl) it is called Hydrohalogenation.
However, Markovnikov’s rule needs to be applied to determine which carbon the hydrogen goes to
and which carbon the halogen goes to. Markovnikov states that the hydrogen will attach to the
carbon with more hydrogens.

38 | P a g e
Water (H2O)
Addition of water is known as hydration. The reaction requires a catalyst such as dilute sulfuric acid.
One of the hydrogens adds to one carbon that was in the double bond and the hydroxide (OH), or
hydroxyl group adds to the other carbon turning the hydrogen into an alcohol. E.g.

Markovnikov’s rule also applies to the hydration.

Investigate, write equations and construct models to represent the

reactions of saturated hydrocarbons when substituted with halogens
A substitution reaction occurs when an atom attached to a saturated hydrocarbon (alkane) is
replaced by different atom. Halogenation occurs when an atom attached to an alkane is substituted
by a halogen. This is because halogens going up group 17 have higher electronegativities than each
other and hydrogen atoms. UV light is needed for substitution reactions to give the energy required
for the reaction to occur. Halogenation occurs in 3 steps:

1. Initiation: When the halogen molecule breaks separating into two separate halogens –
known as radicals (because they have an unpaired electron)

2. Propagation: Then, a radical attaches to a hydrogen to form a hydrogen halide leaving the
saturated alkane with one less hydrogen, and thus one less electron making it an alkane
radical

Then the alkane radical reacts with another halogen to form a halogenated alkane

3. Termination: There are two radicals present at the end other this example; a chlorine radical
(halogen radical) and a methyl radical (alkane radical). These radicals may react with each
other or between themselves as they are highly reactive in their radical state.

39 | P a g e
Substitution can occur multiple times with the products of a halogenated alkane and a hydrogen
halide.

Chapter 11: Alcohols

Investigate the structural formulae, properties and functional group
including: Primary, Secondary and Tertiary alcohols
Straight chain alcohols tend to have higher boiling points than alkanes for a given number of carbons
in the chain. This is because the hydroxyl group in the alcohol is a polar covalent bond and will
intermolecularly bond in hydrogen bonding – the strongest kind of dipole-dipole bonding, which
form far stronger intermolecular bonds than weak dispersion forces. Alcohols additionally have
dispersion forces. Thus, more energy is required to overcome the intermolecular bonds of alcohols
than alkanes.

Alcohols can also be dissolved in water as they form hydrogen bonds with water. However, the non-
polar part of the compound – where the carbon chain is does not form dipole-dipole bonds,
therefore, as the size of the chain increases the less soluble the alcohol will be. This can be seen as
butan-1-ol and onwards are not miscible with water.

−¿¿
Note: Also draw the polarity (ie. δ +¿ and δ ¿
)

Solubility (the amount of solute that can dissolve in a solvent) increases with branching of the
alcohol as the surface area between the alcohol molecules for intermolecular dispersion forces
decreases and thus the hydrogen bonding between the water and hydroxyl group is more easily able
to overcome the dispersion forces to dissolve. All tertiary alcohols are branched and thus tertiary
alcohols are more soluble and secondary alcohols given that the hydroxyl group breaks up the chain
the dispersion forces are weaker and the solubility will greater than primary alcohols but less than
tertiary. As far as solubility goes:

40 | P a g e
The physical property of viscosity (a measure of a fluid’s resistance to flow) is affected by the
structure of the alcohol. Intermolecular forces affect viscosity – the stronger the intermolecular
bonds the more viscous (measured in centipoise cP) the alcohol will be. Thus, the longer the chain
the more viscous, primary will be more viscous than secondary, which will be more viscous than
tertiary and straight chain will be more viscous than branched.

Alcohol combusts. This degree of combustion is considered its flammability. The more carbon-
hydrogen and carbon-hydroxyl group bonds the more energy is required to start the combustion as
there are more bonds to break and thus, the more carbon in the chain the lower the flammability of
the alcohol. But since more bonds are broken more energy will be released.

Alcohols react with metals to form a salt and hydrogen gas. E.g.:

Alcohols react with carboxylic acids to produce esters.

Explain the properties within and between the homologous series of

alcohols with reference to the intermolecular and intramolecular bonding
present
Alcohols homologous series:

Boiling point, melting point and solubility in water (a polar solvent) can be explained by
intermolecular bonds.

However, the solubility of an alcohol is a non-polar solvent is the opposite as for a polar solvent such
as water, whereby, as the chain length increases and the amount of dispersion forces relative to the
hydrogen bonding of the hydroxyl group increases the solubility in a non-polar solvent that breaks
down the intermolecular bonding through dispersion forces will increase.

Ethanol has both a polar and non-polar presence in its molecule and can thus act dually, as both a
polar solvent and a non-polar solvent

41 | P a g e
The intermolecular forces are affected by the positioning of the hydroxyl group. Since the hydroxyl
group forms in the stronger form of bonding – hydrogen bonding the more accessible the hydroxyl
group is to bond with other hydroxyl groups the greater the intermolecular forces between alcohols.
E.g.:

Primary alcohols have hydroxyl groups that are most accessible, thus have the strongest
intermolecular forces – highest boiling point. Secondary alcohols have a less accessible hydroxyl
group, where, as the hydroxyl group shifts more toward the centre of the chain the more restricted
it will be for hydrogen bonding, the weaker its intermolecular forces will be and the lower its boiling
point. This can be seen for the boiling points of the alcohols above.

42 | P a g e
Conduct a practical investigation to measure and reliably compare the
enthalpy of combustion for a range of alcohols
Alcohols undergo combustion to release energy as a decrease in enthalpy from the reactants to
products is present.

Molar heat of combustion: The heat energy produced when one mole of the substance undergoes
complete combustion to produce products in their standard states (25 ℃ and 100 kPa).

Investigation:

Use a spirit burner with the specified alcohol in it to heat a specified amount of water. Measure the
change in temperature of the water as well as the amount of alcohol in grams that was combusted
in grams using a measuring scale. This experiment concludes that the molar heat of combustion of
alkanols increases as chain length increases because the amount of bonds being broken increases.
Also, the longer the chain length of the more incomplete combustion occurs due to the increased
amount of oxygen required for complete combustion, thus, increasing the yield of carbon soot and
carbon monoxide as chain length increases. This investigation has inaccurate equipment and an
open system for heat energy to escape into the surroundings and will thus be invalid and inaccurate
but the results will be consistent, maintaining the experiments reliability.

Write equations, state conditions and predict products to represent the

reactions of alcohols, including but not limited to:
Combustion
Liquid alcohol + gaseous oxygen  carbon dioxide (g) /carbon monoxide (g) /carbon (s) (depending
on amount of oxygen and if complete or incomplete + water liquid

Dehydration
Alcohols can be dehydrated whereby the hydroxyl group and another hydrogen from and adjoining
carbon in the alcohol is taken – it is the opposite of hydration. An alcohol reacts with the catalyst of
concentrated sulfuric or phosphoric acid. This occurs as the hydroxyl group takes a hydrogen from
the acid and breaks off to form water. Then a hydrogen is taken back the acid from the hydrocarbon.
In this process the alkanol forms an alkene. E.g.:

ethanol ⟶ ethene+ water

When for example in the dehydration of butan-2-ol there are two possible products but-2-ene and
but-1-ene by Zaitsev’s rule the extra hydrogen to make the water molecule along with the hydroxyl
group will be generally taken from the neighbouring carbon with the least amount of hydrogens.
This means that the major product in this example in but-2-ene

Substitution with HX
Then halogen can substitute for the hydroxyl group. E.g.:

To separate out the bromoethane the solution would need to be heated and then bromoethane
separated through distillation

43 | P a g e
Oxidation
Alcohols can be oxidised in a multitude of ways whereby an oxygen is added. Primary alcohols can
be oxidised to form carboxylic acids or aldehydes. Secondary alcohols can be oxidised to ketones.
Tertiary alcohols cannot be oxidised as the carbon can only have four bonds, not five.

Investigate the production of alcohols, including:

Substitution reactions of halogenated organic compounds
The polarity of a carbon – halogen bond depends on the electronegativity of the halogen whereby,
the halogen end is the sigma negative and the carbon end is sigma positive. Nucleophiles (molecules
or ions strongly attracted to delta positive atoms because they are either negatively charged or are
delta negative themselves) will attract to this delta positive carbon and then substitute with the
halogen to form alcohol. These are some nucleophiles are their relative strengths:

In the production of alcohol a compound containing hydroxide (the hydroxyl group of an alcohol) is
dissolved and reacted in an aqueous solution with a haloalkane to form the alcohol and the halogen
ion. E.g.:

Fermentation
Fermentation is the reaction, whereby sugars are converted under anaerobic (absence of free
oxygen) condition to ethanol and carbon dioxide. This can be done using a solution of glucose, yeast,
nutrients for the yeast (e.g. Pasteur’s salt), temp of 37 ℃ , and anaerobic conditions (closed vessel,
no added oxygen). When yeast are deprived of oxygen they respire the glucose to obtain energy,
producing ethanol and carbon dioxide:

44 | P a g e
A catalyst such as zymase may also be used.

In an experiment for fermentation, if a known glucose solution is fermented, the amount of carbon
dioxide that has escaped will indicate to amount of ethanol formed given that the fermented
solution will lose mass when it loses carbon dioxide. A control without yeast will also need to be set
up to account for evaporation of the water over the fermentation period. Ethanol can then be
fractionally distillated given that its boiling point is 78℃ .

Investigate the products of the oxidation of primary and secondary

alcohols
Alcohols can be oxidised using acidified potassium dichromate ( K 2 Cr2 O 7) or acidified potassium
permanganate ( KMn O 4 ) as the catalyst, known as an oxidising agent and can be represented by
−¿¿
[O]. Acidified means that these oxidising agents have split into their ions, where the Mn O 4 and
2−¿¿
Cr 2 O7 are the catalysts in this aqueous form, without the potassium.

In both reaction of primary alcohols to aldehydes and secondary alcohols to ketones an electron is
lost by the . This must be balanced by two electrons. Also, to oxidising agent must be indicated
above the reaction arrow:

Compare and contrast fuels from organic sources to biofuels, including

ethanol
Organic sources of fuel include fossil fuels (e.g. octane from crude oil) or renewable resources such
as biofuel. Biofuels such as ethanol can be obtained renewably from the biomass being sugarcane by
the fermentation of its sugars. Ethanol is also more likely to undergo complete combustion as it
needs less oxygen than octane etc. so is therefore further better for the environment, and also
produces less carbon dioxide as well:

45 | P a g e
Ethanol can also be considered clean and better for engines. This is because it would be good at
dissolving deposits in the engine due to its versatility as a solvent. So the engine would be cleaner
and run smoother. Ethanol also has a higher flash point and thus is less readily combustible at room
temp, leading to less accidents.

However, ethanol if falsely referred to as a carbon neutral fuel. Fermentation to create ethanol is
also not economically viable and our current cars would require new engines to safely combust
ethanol.

Biodiesel can also be formed from vegetable oils – e.g. canola, palm rapeseed. Biodiesels have a long
hydrocarbon chain with an ester linkage at the end and are very similar to the structure of diesels,
thus no engine modification is needed for current diesel burning cars. Biodiesel also has a much
higher flash point than diesel and is safer to handle and store

Chapter 12: Reactions of organic acids and bases

Investigate the structural formulae, properties and functional group
including: primary, secondary and tertiary alcohols, aldehydes and
ketones, amines and amides and carboxylic acids. Investigate the
structural formulae, properties and functional group for amines and
amides. Investigate the structural formulae, properties and functional
group for carboxylic acids. Explain the properties within and between the
homologous series of carboxylic acids, amines and amides with reference
to the intermolecular and intramolecular bonding present
Aldehydes are ketones have similar properties as they both contain the polar carbonyl group. This
polarity allows for dipole-dipole bonding allowing ketones and aldehydes to have a higher
melting/boiling point than non-polar alkanes but a lower than alcohols which have a hydrogen
bonding. Carboxylic acids, which have dispersion forces in their main chain and both dipole-dipole
and hydrogen bonding in their carboxyl group, thus having the strongest intermolecular bonds and
the higher melting/boiling points:

46 | P a g e
Aldehydes/ketones with up to four carbons are miscible in water:

Additionally, the double bond of the carbonyl group attract nucleophiles (attracted to the carbon
sigma positive end).

Amines can be primary, secondary or tertiary. Primary amines have 2 points of hydrogen bonding
and will thus have greater intermolecular bonds and most polarity given they have 2 hydrogens
attached and only one carbon. Secondary amines are thus less and tertiary are even weaker
intermolecular bonds.

Amides can be made through a reaction between from the dehydration (meaning water is lost)
reaction between ammonia and a carboxylic acid under heat and in the presence of an acidic
catalyst. Once again, primary amides given they have a higher proportion of hydrogen bonding
compared to dipole-dipole have stronger intermolecular bonds and are more polar than secondary
and then tertiary amides. Primary and secondary amides given that they both have a N-H bond can

47 | P a g e
form dimers between the C=O bonds and the N-H bonds greatly increasing the intermolecular bonds
of these amides – some amides are solid at room temperature. Dimer:

Additionally, carboxylic acids ca form dimers which also drastically increases the intermolecular
bonds strength:

An interesting property of long chain carboxylic acids is that the molecules line up along the surface
of water with their non-polar tails up and their highly poplar carboxyl functional groups in the water
– they are known as surfactants. Carboxylic acids as they name suggests are acidic. They are weak
monoprotic acids – this will be discussed later.

Describe the procedures required to safely handle and dispose of organic

substances

Investigate the production, in a school laboratory, of simple esters

Esters can be created from the reflux reaction of an alkanol and alkanoic acid in the presence of a
concentrated acid (e.g. sulfuric acid) – this process is known as Esterification. Esterification is in a
dynamic equilibrium and to shift the equilibrium to the right producing more ester heat should be
used and the catalyst (sulfuric acid) is used since this is a dehydration reaction as water is lost. The
reactants of esterification are volatile (meaning the reflux is used to condense evaporated reactants)
and flammable (safety: no naked flame used, use a water bath. In this reaction boiling chips are used
to avoid large bubbles and the apparatus is not closed by a plug to avoid a build up of pressure and
the glassware to explode. Also, a round bottom flask is used. This is the esterification formula:

alkanol +alkanoic acid ⇌ water +ester

This process may take 3-4 hours.

Esters formed can be further distilled from the other reactants and products still remaining by
dissolving the others – esters are the least soluble in water and so can be decanted as they form the
layer on the top. Furthermore, a base such as sodium hydrogen carbonate can be used to neutralise
any remaining carboxylic acid. Finally fractional distillation.

48 | P a g e
Safety: Concentrated sulfuric acid, no naked flame – water bath, no build up of pressure from
stopper.

To name a ester:

- Start with the alcohol, replacing “anol” with “yl”: propanol  propyl
- Then with the carboxylic acid, replacing “oic” with “oate”: butanoic acid  butanoate
- Finally, combine them: propyl butanoate

This is what an ester reaction looks as well as the ester functional group.

It is important the note that to OH group of the carboxylic acid and the H of the alcohol are used to
create the water and the alcohol and carboxylic acids are joined by the oxygen.

49 | P a g e
Esters have dipole-dipole bonding. Thus, they are less polarity and weaker intermolecular forces
than alcohols or carboxylic acids. Esters can be hydrolysed, under the influence of bases (e.g. NaOH),
to alcohols and alkenoate ions (They do not have their hydrogen ion attached):

Investigate the differences between an organic acid and organic base

Organic Acids
Organic acids generally comprise of carboxylic acids, but may also by alcohols or phenols (weaker
than carboxylic acids):

These molecules are weak acids and are proton donors (acids) due the their hydroxyl group (OH). In
this equilibrium reaction the organic acid will be ionised by removing the hydrogen from the
hydroxyl group into the solution.

50 | P a g e
In terms of acid strength; carboxylic acid > phenol > alcohol. This is due to the differing strengths of
the O-H bond that is broken and the stability of the conjugate base. The stability of the conjugate
base is dependent on the tendency of the conjugate to form back wit hydrogen in the reverse
direction.

Within the carboxylic homologous series, methanoic acid is the strongest as it has no alkyl group
which may push the hydrogen cation to the negative end:

However, more electronegative halogens (e.g. fluorine) are attached to the alkyl group the alkyl, the
alkyl group end will become less positive and will thus push the hydrogen to the negative end less
making the conjugate base more stable and thus these carboxylic acids that have halogenated alkyl
groups are much stronger.

Organic bases
Amines can accept protons and are thus a weak base. The bases strength is dependent on its ability
to accept the proton and the stability of the conjugate acid formed. Aliphatic amines have at lest 1
alkyl group – carbon chain, they are nucleophiles and are bases. Aromatic amines are amines
attached to a benzene ring, they are also basic. These amines bases require a water solvent to react,
thus, as their non-polar end increases in size they solubility decreases, and thus there strength to
dissociate in water decreases

Investigate the structure and action of soaps and detergents

Fatty acids are carboxylic acids with very long chains. The sodium and potassium salts of these fatty
acids can be used as soaps. Soaps are usually made from vegetable oils or fats by saponification –
The conversion in basic solution of fats and oils to glycerol and salts of fatty acids in an alkaline
solution.

These fats and oils contain an ester known as triglyceride.

51 | P a g e
The triglyceride is reacted with a base (e.g. NaOH) to be hydrolysed base into 3 glycerol and three
fatty acids that are alkanoates that have formed a salt with the sodium ion.

Detergents were made due to a shortage in animal/vegetable fats, instead are derived from
petrochemicals so are non-biodegrable.

Soaps and detergents act as surfactants as they reduce the surface tension of water and allow an
emulsion to be formed. An emulsion is a mixture of two liquids where tiny droplets of one liquid is
found dispersed through the other. A mixture composed of soap or detergent with water and grease
or oil (that is needed to be cleaned) is an emulsion. A soap has its polar, hydrophilic alkanoate end
and the non-polar, hydrophobic alkyl end. In cleaning, rubbing can loosen grease on a shirt and the
non-polar end of multiple soap molecules surround the grease molecule in a spherical micelle while
the polar end stays dissolves in the water. This ensures an emulsion, where the grease does not
clump together due to the negative charges of the outward facing oxygens. When the emulsion is
washed away so to the micelles of grease.

Soap is ineffective in pH below 4.5 and in hard water (water with high concentration of magnesium
and calcium ions). In acidic water that alkenoate end attached to free hydrogen ions to form
carboxylic acid. And magnesium/calcium ions form precipitates with the soaps – these precipitates
give the physical appearance of scum.

Detergents lather in hard water as they do not precipitate with magnesium/calcium, however, hard
water still limits the effectiveness of detergents. Phosphates may be added with detergents in
cleaning products to bind to these hard water ions. Detergents have a long alkyl tail but they vary in
the charge of the polar head:

- Anionic head; is affected by hard water molecules

- Cationic head; not affect by hard water molecules as it is the same charge as the calcium and
magnesium ions
- Non-ionic head (the head will be polar though)

52 | P a g e
Draft and Construct flow charts to show reaction pathways for chemical
synthesis, including those that involve more than one step
Flow charts can be used to show sequences of organic chemical reactions. E.g.:

Chapter 13: Polymers

Cracking involves splitting a longer chain alkane into one alkane and one alkene to create more
useful products. This can be via catalytic (using catalyst) or thermal cracking (through heat). Catalytic
is better because it is cheaper because no heating is required, produces more useful products
aromatics and branched alkanes (burn easier). These made alkenes comprise the monomers used for
polymerisation

A monomer are the individual building blocks of an infinitely long polymer. A polymer’s systematic
name is poly”monomer”.

Addition Polymers
Many alkenes adding together.

Additional polymerisation occurs in three main steps:

53 | P a g e
 1. Initiation: A peroxyl free radical attaches to a monomer on one of the carbons in double
bond, stealing one of the electrons in that sigma bond. This creates a radical (free electron)
on the other carbo in the double bond
2. Propagation: The carbon with the radical bonds with another monomer in a similar fashion
to the initiation process whereby the terminal carbon in now the new radical. This repeats
thousands of times
3. Termination: Another peroxyl free radical pairs up with the final carbon radical and the
chain is finished (Chemical inhibiter termination) or, more commonly two growing chains
will combine (Chain collision termination)

Polyethylene (PE)
Polyvinyl chloride (PVC)
Polystyrene (PS)
Polytetrafluoroethylene (PTFE)
Polymer Name Monomer Name How made Properties Uses
and systematic
name
HD polyethylene ethene Low pressure, hot Non- Furniture,
(HDPE) (but less temp than branched kitchen
LDPE) and Ziegler- (more utensils,
Natta catalyst dispersion – toys
(triethylaluminium). denser,
harder,
higher mp.)

Non-polar –
hydrophobic,
immiscible
LD polyethylene (LDPE) Hot, high pressure Has branched Plastic bags,

54 | P a g e
 and initiator polymers due food wrap
chemical. Cheaper to longer
and easier to make. monomers
(less
dispersion –
melting point,
softer, more
flexible)

Non-polar –
hydrophobic,
immiscible
Polyvinyl chloride (PVC) Vinyl chloride Polar Cl Piping,
(dipole-dipole electrical
forces – cords, floor
chloroethene higher mp, tiles
rigidity and
toughness),
highly
resistant to
breakdown
by chemicals,
bacteria and
UV). Not
polar enough
to be miscible
with water
Polystyrene (PS) Styrene Phenol group Heat
increases insulation,
strength of foam,
dispersion surfboards,
Phenolethene (toughness), esky
as well as
rigid
structure
(brittle). High
refractive
index -
opaque
Polytetrafluoroethylene High chemical Used in
(PTFE) resistance, Teflon (non-
low friction, stick pans),
electric and Gore-Tex
tetrafluoroethene heat textiles
insulative.
Very polar,
dipole-dipole
Addition polymers are not biodegradable and are incinerated by release all products of
complete/incomplete combustion.

55 | P a g e
Condensation Polymers
Formed by condensation reactions between two different alternating monomers, which releases a
small by product molecule (typically water). Cellulose in a condensation polymer, repeating units of
glucose whilst produce water each time. Condensation polymers can biodegrade or can be
converted back into monomers by hydrolysis (NaOH).

Polyester
Polyesters form ester linkages between there monomers. One monomer is a dicarboxylic acid (with
carboxyl groups at both ends) and the second monomer is a diol (with two hydroxyl groups at the
end). Produces water as small molecule by product. Polyester, is strong, elastic and electrically
insulative and is used as the textile polyester due to its minimal absorption of water and shrinkage
when washed.

Nylon (Polyamide)
Nylon forms amide linkages between their monomers. One monomer is a diamine and one is a
dicarboxylic acid. Also produces water. Used for stockings.

Module 8: Applying Chemical Ideas

Chapter 14: Analysis of Inorganic substances
Analyse the need for monitoring the environment
Although many ions are helpful to the environment, some are toxic and some in excessive amounts
are detrimental to the air, soil or water. For example:
2+¿ ¿
Cu : Used by some crustaceans to carry oxygen around their bodies – can be toxic in high
amounts. Enters environment through corrosion of copper pipes or paint
2+¿ ¿
Pb : Is a neurotoxin and is toxic. Can enter the environment through leaded oil (banned in 2002)
or old paint.

Sulphates and Phosphates: Excessive amounts can cause algal blooms (such as in Darling River 1991)
due to the run off of fertilisers. This algae blocks sunlight for photosynthesis for aquatic flora and
releases toxins when they decompose.

Conduct qualitative investigations – using flame tests, precipitation and

complexation reactions as appropriate – to test for the presence in
aqueous solution of ions
+¿¿
It is possible to test for cations: Cu2+¿ ¿, Ba2+¿¿ , Mg 2+¿¿ , Pb2+¿ ¿, Ca2+¿ ¿, Ag , Fe2 +¿¿, Fe3 +¿¿ using:

- Precipitation: NAGSAG SML CASTROBEAR, Fe2 +¿¿, Mg 2+¿¿ , Cu2+¿ ¿ and Fe3 +¿¿ can be
distinguished by the colour of the ion that they form with dilute sodium hydroxide ( Fe3 +¿¿:
orange precipitate, Mg 2+¿¿ : white, Cu2+¿ ¿: Blue, Fe2 +¿¿: green precipitate), to differentiate
barium and calcium, calcium creates a precipitate with hydroxide solution. Can differentiate
silver (coffee) and lead (white) using a hydroxide.

56 | P a g e
 - Flame test: different metals burn different colours (Cu2+¿ ¿: Blue, Ba2+¿¿ : green apple,
2+¿¿ 2+¿ ¿ 2+¿ ¿ +¿¿
Mg : n/a, Pb : White out with a tinge of blue, Ca : brick red, Ag : light blue grey,
2 +¿¿ 3 +¿¿
Fe : golden yellow, Fe : orange/ brown)
- Complexation reactions: These involve a central metal ion (cation) attached to a number of
smaller molecules or ions – known as ligands. Ligands create a coordinate covalent bond
(two electrons derive from the same atom) with the metal. This determines the colour of
this solution due to EMR being absorbed by the metal where different ligands may result in
different wavelengths of visible light being absorbed.
−¿¿ −¿¿ −¿¿ −¿¿ −¿ ¿ −¿¿ −¿¿
OH Cl I F S O4 Mn O4 SCN N H3 Flame test Complexa
tion
2+¿ ¿
Cu blue Dissolv Blue/green Blue in
es ppt water
with
OH
Ba
2+¿¿
whit green
e
Mg
2+¿¿
whit whit Does n/a
e e not
dissolv
e ppt
with
OH
2+¿ ¿
Pb whit whit yello whit Pale blue
e e w e
2+¿ ¿
Ca whit whit whit Brick red
e e e
+¿¿
Ag bro whit Pale Grey/blue
wn e yello

57 | P a g e
 w
2 +¿¿
Fe Gree ppt Decolouri Iron man Pale green
n or sed it yellow in water
whit
e
3 +¿¿
Fe Bro ppt Dee Orange/ Orange in
wn p brown water
red
Procedure:

1. Chloride: To find if lead or silver (distinguish between the two using hydroxide)
2. Sulphate: To find barium and calcium (distinguish between the two using hydroxide or flame
test)
3. Hydroxide: Distinguish between magnesium, copper and the two irons (to further distinguish
the irons use thiocyanate)
−¿¿ −¿¿ −¿¿ −¿¿ −¿ ¿ 2−¿¿ 2−¿¿ 3−¿¿
For the anions: Cl , Br ,I , OH , C H 3 COO , C O3 , S O4 , P O4 :

Conduct investigations and/or process data involving:

These techniques determine the concentration of the ion present quantitatively

Gravimetric analysis
Can be used for both aqueous and solid ions. One form of gravimetric analysis is precipitation
gravimetry with for example chloride, whereby the ions is precipitated out of an aqueous solution
using an excess of silver nitrate solution, and the precipitate’s mass is measured. To ensure a correct
volume of the solution use a 20 mL bulb pipette, where the solid should be procured by evaporating
the remaining liquid. To ensure that an excess of silver nitrate solution is added, make sure it is high

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concentration and when a precipitate is formed filter out the remaining solution and add extra silver
nitrate solution to it, to test whether a precipitate will still form – this means that there is still
chloride ions to precipitate out.

Precipitation titrations
An indicator (e.g. Potassium Chromate K 2 Cr O4 ) can be used to determine when the equivalence
point of the precipitation reaction has been reached. This uses the same techniques for titration are
used. Again, to find the concentration of chloride ions in solution a volume of it is titrated against a
known concentration volume of silver nitrate in the presence of a potassium chromate indicator.
Initially, when chlorine ions are in excess the potassium chromate gives the solution a yellow colour.
However, at the point of equivalence when silver ions become in excess the potassium chromate
reacts with the silver nitrate given the solution an orange colour. Thus, the slightest colour change
indicated the equivalence point

Conduct investigations and/or process data to determine the

concentration of coloured species and/or metal ions in aqueous solution,
including but not limited to, the use of:
Colourimetry
Particularly transition metal ions form brightly coloured complexes. A colourimeter uses a light
source passes through a coloured filter to test the absorbance of the certain metal as a complex or a
ion. The light the passes through to the photocell is then converted into an absorbance value. This
colour is chosen to be the colour the is most strongly absorbed by the ion (For example: the complex
of copper and ammonia that is deep blue will most strongly absorb yellow, thus a yellow filter will be
used)

The more concentrated the solution of the sample is the more light of the certain colour it will
absorb and thus the higher absorbance value it will receive. To determine the concentration of an
unknown sample a dilution series of varying concentrations of that solution should be tested for
absorbance. Their values for absorbance should then be plotted on a graph to create a calibration
curve. Using this curve the concentration of the unknown concentration solution can be then known
using its absorption value to find its corresponding concentration

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Colourimetry is economic and accessible but not a very accurate form of absorption spectrometry.

Ultraviolet-visible spectrophotometry
Tests the absorbance of a solution over a wide range of UV and visible wavelengths of light, to
determine discrete values of absorbance over a range of wavelengths due to specific transitions of
electrons between energy levels – excited electrons. The sample of the solution is placed in a cell
known as a cuvette and its absorbance is may be tested against a reference cuvette with the solvent
it was in (e.g. water, hexane or ethanol). A calibration curve may be used similar to colourimetry or
the Beer-Lambert Law:

A chromophore is any covalently bonded group of atoms that have a characteristic absorption of
radiation in the UV or Visible spectrum.

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 Io
The absorbance can also be calculated using log 10 ( ), where I o is the intensity of the entering
I
beam and I is the intensity of the exiting beam

Atomic absorption spectroscopy

Relates to analysing the wavelengths of light absorbed by an substance in its observed absorption
spectrum when heated. This is done by vaporising (using a chopper) the substance into an aerosol so
it can be heated. Similar to colourimetry known concentration reference samples are used to create
a calibration curve. A monochromator selects a discrete wavelength of light that is subsequently
measured by a detector that is specific to the tested elements characteristic absorption line.

Chapter 15: Analysis of organic substances

Conduct qualitative investigations to test for the presence in organic
molecules of the following functional groups:
Carbon–carbon double bonds
Alkene and alkane can be distinguished by Bromine water experiment (safety: bromine is toxic – use
fume cupboard and use a collection vessel to safely dispose organic waste). Additionally, the alkene
and alkane must be liquid at room temp, thus use cyclohexene and cyclohexane and use excess of
the hydrocarbon. This is what the reaction will look like in the end:

Hydroxyl groups
The Lucas Test can test for hydroxyl groups, distinguishing between primary, secondary and tertiary
alcohols. The Lucas reagent is a mixture of concentrated HCl with anhydrous zinc catalyst (safety:
alcohol – keep away from flame, HCl – corrosive – safety googles/gloves/rinsing, collection vessel
needed)

At room temp tertiary react via substitution to form a cloudy alkyl chloride (as the alkyl chloride is
immiscible) immediately, secondary react slowly to form a cloudy alkyl chloride, while primary do
not react. Therefore, reactivity with Lucas Reagent is given as tertiary > secondary > primary.

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Carboxylic acids
Carboxylic acids are weak acids that may be detected by reacting them with a base (such as sodium
hydrogen carbonate NaHC O 3 ) to form a salt, water and carbon dioxide. Thus, this reaction can be
detected by lime water in the equation:

C O2 +Ca(OH )2 ⟶CaC O3 + H 2 O
The lime water will turn cloudy due to the formation of calcium carbonate it is truly a carboxylic acid.

Investigate the processes used to analyse the structure of simple organic

compounds addressed in the course, including but not limited to:
These processes can detect the functional groups in organic compounds as well as their spatial
orientation.

Proton and carbon-13 NMR

Nuclear magnetic resonance spectroscopy or NMR uses interactions between atoms and a magnetic
field as well as EMR. NMR utilises the concept that when placed in a magnetic field the nuclei of
some atoms absorb radiation in the radio wave spectrum of EMR. These nuclei have a property
called spin – as they spin they create a magnetic field. hydrogen-1 (a proton) and carbon-13 are
atomic nuclei with spin as they both have an uneven ratio of protons and neutrons. This is important
as both carbon and hydrogen are found in organic compounds. A hydrogen-1 nuclei when subjected
to a external magnetic field can be spinning so that its created magnetic field aligns with the external
magnetic field, or spinning in the opposite direction so that its created magnetic field is opposing the
external magnetic field in the opposite direction:

When radio waves of correct frequency (essentially a resonant frequency), the EMR is absorbed by
the nuclei spinning in the opposing direction, so that their spin is flipped to align with the external
magnetic field.

In NMR spectroscopy, the sample placed in an appropriate solvent in a glass tube. The tube is placed
within an external magnetic field and is irradiated with radio waves causing the hydrogen-1 nuclei
within the sample to become ‘excited’. The emitted energy is then detected by a receiver.

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The electrons that surround a nucleus shield it from the field. The positions of these electrons and
thus the degree of shielding that they are capable of is dependent on the nature of the surrounding
atoms – this is known as environment of the nucleus. For example in 1-2 dichloroethane:

Each hydrogen-1 is bonded to one carbon – uniform nuclei environments for all hydrogen-1.
Similarly, each carbon is bonded to 2 hydrogens and 1 chlorine – uniform nuclei environments for all
carbon (including the carbon-13 isotope). Conversely, ethanol:

Ethanol, different nuclei environments for both their hydrogens and their carbons.

Different nucleus environments result in chemical shifts in tetramethylsilane (TMS) – the reference
substance for NMR:

The term chemical shifts relates to the position of the peaks along the carbon-13 NMR spectra – if
there is multiple nucleus environments their will be multiple peaks. These peaks roughly indicate
what nucleus environment the carbon is in

Hydrogen NMR spectra can identify the number of hydrogen nuclei as well as their arrangement.
The area of the hydrogen NMR peaks indicates the relative number of hydrogen nuclei. Hydrogen
atoms bonded near to more electronegative atoms have a greater chemical shift value. The number
of neighbouring hydrogen atoms attached to the same atom can be approximately determined by
the splitting pattern of the peak:

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Mass spectroscopy (ACSCH19)
In mass spectroscopy a small sample of the compound is vaporised, and then bombarded with high
energy electron beams causing the sample to break into positively charged fragments. These positive
fragments are accelerated in an electric field and then separated using a magnetic field based on
their relative charge to mass ratio (m/z). The abundance of each value of mass to charge ratio is then
graphed:

The charge to mass ratio values corresponds to the formation of ions, where different compounds
fragment in characteristic ways

Infrared spectroscopy
Helps identify functional groups. IR spectroscopy uses the theory that atoms can move around their
bonds due to their dipole, which are not rigid. Different bond types absorb energy at different

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wavelengths and thus different functional groups will produce peaks absorption of IR spectrum of
different shapes and intensities.

The graph is x-axis (wavenumber per cm) by y-axis (absorption increasing down the axis).

- Primary amine – fangs

- Secondary amine – one fang
- Carboxylic O-H – beard
- Alcohol O-H – tongue
- C=O – sword

Overall:

1. use IR spec first to find the specific bonds of the molecule and thus the functional group and
find the basic empirical formula of the molecule
2. use mass spec second to find the molecular mass of the molecule to find the basic molecular
formula of the atom
3. Finally use NMR to find how many carbon/hydrogen environments to determine the
structural formula of the atom

Chapter 16: Chemical synthesis and design

Evaluate the factors that need to be considered when designing a
chemical synthesis process, including but not limited to: Availability of
reagents, Reaction conditions, Yield and purity, Industrial uses (e.g.
pharmaceutical, cosmetics, cleaning products, fuels), Environmental,
social and economic issues
Chemical synthesis uses a sequence of chemical reactions to yield a useful product. There are a
range of implications to society relating to various case studies of chemical synthesis

Early Chemical synthesis:

The willow tree has been used since the ancient Egyptians for pain relief. In 1700, it was proved to ail
fevers and in the 1800’s a German scientist isolated the active ingredient – salicin. This compound is

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converted in the body to salicylic acid. Later, to yield salicylic acid from salicin scientists used
hydrolysis to convert salicin to salicyl alcohol, oxidising salicyl alcohol to produce to salicylic acid.
However, this pain relief was found to damage to mouth and stomach causing vomiting. In 1897,
Felix Hoffman synthesised acetylsalicylic acid – known commonly as aspirin. He did this by replacing
the hydroxyl group with an acetate ester, thus creating an effective pain killer that caused less
irritation to the digestive tract. Today the Kolbe-Schmitt process is used in the synthesis of
acetylsalicylic acid from phenol.

Aspirin is considered a non-steroidal anti-inflammatory drug, but has been found to cause stomach
ulcers and can prove fatal for children. Thus, the need for a replacement/alternative was needed. In
the 1950’s, Dr. Stewart Adams synthesised 2-(4-Isobutylphenyl)propionic acid or “ibuprofen”.
Similarly classed as a non-steroidal anti-inflammatory drug and similarly as effective, the drug does
not cause ulceration. Ibuprofen involves optical isomerism (a form of isomerism where isomers are
a mirror image of each other making their atoms arrange slightly differently), where only one optical
isomer (S)-ibuprofen has anti-inflammatory properties, where (R)-ibuprofen, is otherwise inert but
can convert into (S)-ibuprofen using enzymes in the body. However, different optical isomers can
prove detrimental. Thalidomide – an anti-nausea drug, commonly giving to pregnant women was
found to cause higher rates of birth defects and infant mortality. In this case the R isomer was
effective in treating nausea while to S isomer was a teratogen (a chemical that causes birth defects).
Although it is possible to isolate the R isomer, it can be converted b enzymes in the body into the S
isomer. Even though thalidomide was only available for a short time, the horrific damage it caused
led to tightened requirements for clinical trials, including separate testing of isomers. This
demonstrates the importance of considering ethical issues and pharmaceutical usage in drug design.

Green chemistry aims to reduce waste and production of harmful compounds leading to a new
synthesisation process for ibuprofen. This process reduces the number of steps from 6 to 3. At each
step a percentage of the yield is lost and thus fewer steps results in less potentially harmful waste,
less reactants are used and a higher yield. The new method uses hydrogen fluoride and nickel as
catalysts, and they are regenerated and able to be reused after the reaction. In contrast, the earlier
method of ibuprofen synthesis used aluminium chloride that was not a true catalyst as it was not
recoverable and went to landfill. The two methods of synthesising ibuprofen demonstrates the
importance of considering yield, environmental issues and reaction conditions when designing
effective chemical synthesis pathways.

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