Module 7 Summary Notes

IQ1: Nomenclature
Inquiry Question: How do we systematically name organic chemistry compounds?

Syllabus Dot Point:

Investigate the nomenclature of organic chemicals up to C8, using IUPAC conventions,
including simple methyl and ethyl branched chains, including: (ACSCH127)
- Alkanes
- Alkenes
- Alkynes
- Alcohols (primary, secondary and tertiary)
- Aldehydes and Ketones
- Carboxylic Acids
- Amines and Amides
- Halogenated Organic Compounds

• Carbon has 4 valence electrons; therefore, carbon can form a maximum of 4 covalent
bonds
• Carbon can undergo catenation – the process by which many identical atoms are
joined together by covalent bonds

Types of Organic Compounds:

Straight Chain: Carbon atoms are in a straight line

Branched: Carbon atoms are not in a straight line

Cyclic: Carbon atoms are in an enclosed shape

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Hydrocarbons
• Contains only hydrogen and carbon

Naming:
Prefix – number of carbon atoms in the longest C chain
Suffix – type of organic compound (e.g. alkane)

Locants
- A number in the middle of the compound name to identify the position of a C=C or
C≡C bond
- Always minimise the locant

Alkanes: Contain only single C-C bonds (CnH2n+2)

Alkenes: Contain at least one double C=C bond (CnH2n)
Alkynes: Contain at least one triple C≡C bond (C nH2n-2)

Substituent: an atom or group of atoms which replaces one or more hydrogen atoms on the
parent chain of a hydrocarbon, forming a new molecule

Alkyl group:
• Methyl – CH3
• Ethyl – CH3CH2
• Propyl – CH3CH2CH2

2-methylpentane

- Locant of substituent
- Name of Alkyl Chain
- Straight chain compound

• When naming, the substituent is a prefix to the nomenclature of the parent chain

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Saturated compound – contains the maximum number of atoms within the compound;
therefore, exclusively single C-C bonds are present

Unsaturated compounds – do not contain the maximum number of atoms; therefore, double
and triple bonds are present

Organic compounds can be represented in:

• Lewis structures – useful to visualise the valence electrons present in simple molecular
compounds
• Empirical formulae – represents the simplest ratio of atoms present in a molecule
• Structural formulae – shows all the atoms in their position

Aromatic and cyclic hydrocarbons:

• Organic compounds when the structure is in an enclosed shape
• Aromatic hydrocarbons are characterised by the presence of Benzene (C 6H6)

Functional Groups
Substituents that provide distinctive chemical properties

Name of Suffix General Structure (R is Example

Functional a carbon chain)
Group
Haloalkane -ane R-X

X is any halogen (e.g. Cl,

F, Br) Bromoethane

Alcohol -ol R-OH

Ethanol

Aldehyde -al

Butanal

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 Ketone -one

Propanone

Amine -amine

Amphetamine

Amide -amide

methanamide

Carboxylic -oic acid

Acid

Ethanoic acid
Sidenote: both aldehydes and ketones contain a carbonyl group (=O), however, for aldehydes,
the carbonyl group is on the ends of the compound whereas for ketones, the carbonyl group is
somewhere in the middle

Isomers
Syllabus Dot Point: Explore and distinguish the different types of structural isomers, including
saturated and unsaturated hydrocarbons, including: (ACSCH035)
- Chain isomers
- Position Isomers
- Functional Group Isomers

• A group of compounds which have the same formula, but a different structure

Chain isomers:
Carbon skeleton is rearranged
- Different lengths of parent chain
- Branches into side chains

Position isomers (only applies to functional groups):

- The locant of the functional group differs

Functional group isomer:

Different functional group (only works for specific functional groups)
- Ester Acid
- Straight chain alkane cycloalkane

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 - Ketone Aldehyde

Homologous series: molecules with the same functional group

IQ2: Hydrocarbons
Inquiry Question: How can hydrocarbons be classified based on their structure and
reactivity?

Models:
Syllabus Dot Point:
construct models, identify the functional group, and write structural and molecular formulae for
homologous series of organic chemical compounds, up to C8 (ACSCH035)
- Alkanes
- Alkenes
- Alkynes

Ball and Stick model (1)

Structural formulae (2)

Space filling model (3)

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Advantages
- (1) + (3) demonstrate relative size + a 3D geometry
- All models depict a difference in the atoms of different elements
- (1) + (2) are able to demonstrate a difference in single, double and triple bonds

Disadvantages
- (3) cannot depict bonds
- All models are not to scale

Shape of molecules:
Syllabus Dot Point: Analyse the shape of molecules formed between carbon atoms when a
single, double or triple bond is formed between them

VSEPR theory:
The arrangement of electron pairs in a way which minimises electrostatic repulsion

Bond location - electrons which are shared between atoms Covalent bonding is present
No lone pairs

• 4 Bond locations = tetrahedral

• 3 Bond locations = trigonal planar
• 2 Bond locations = linear

Alkanes:
• In methane – 4 identical C-H bonds are present tetrahedral shape

Therefore: In an alkane, around each carbon atom, tetrahedral geometry is present

- All alkanes are a collection of carbon atoms with single bonds which have tetrahedral
geometry

Alkenes: Trigonal planar all components lie in 1 plane

Alkynes: Linear

A hydrocarbon can have a combination of tetrahedral, trigonal planar and linear geometry
present. The geometry around the carbon is dependent on the type of bonding (single, double or
triple)

Physical properties of hydrocarbons

Syllabus Dot Point: explain the properties within and between the homologous series of alkanes
with reference to the intermolecular and intramolecular bonding present

Intermolecular forces:

1. Dispersion forces
• Present between all molecules, however, when the molecule is non-polar, dispersion
forces are the only force present
• Weakest type of force

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 • Attraction is formed through the formation of a temporary dipole which induces a dipole
in the neighbouring molecule
• More electrons stronger dispersion force

2. Dipole-dipole
• Form between polar molecules as polar molecules have a permanent uneven electron
distribution
• Due to the large electronegativity difference between the bonded atoms, a polar covalent
bond with a permanent dipole is formed

3. Hydrogen bonding
• Strongest form of dipole-dipole force
• Occurs between Hydrogen and either F, O or N. The hydrogen has to also be bonded to
either F, O or N for there to be a significant electronegativity difference

Boiling Points
• All Hydrocarbons are non-polar dispersion forces present between molecules

As the length of the parent chain increases BP increases

- More carbon atoms more electrons stronger temporary dipoles stronger
dispersion forces

Boiling points of homologous series are compared to alkanes as they are the most basic form of
organic compound

Alkanes:
Straight chain alkanes have a higher boiling point than branched isomers
- Straight chain alkanes can compact/tessellate more easily greater surface contact
greater surface area to form dispersion forces + can form over a shorter distance
more dispersion forces and stronger dispersion forces will form higher BP

Alkenes:
Alkanes and Alkenes have a similar boiling point as they have a similar chemical composition

Alkynes:
Alkynes have a higher Boiling Point compared to alkenes and alkanes
- Linear geometry of alkynes easier for the molecules to compact greater surface
area for dispersion forces to form + molecules are closer together meaning stronger
dispersion forces can form

Haloalkanes:
Haloalkanes have a higher Boiling Point compared to alkanes
- Polar nature of haloalkanes means that dipole-dipole forces can occur
- Note that H-Bonding cannot occur as the hydrogen is bonded to the carbon

Carboxylic Acids + Alcohols (In depth analysis in later IQ’s)

• Boiling points of Carboxylic Acids and Alcohols are greater as there is h-bonding present

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The presence of branching chains in hydrocarbons lowers the boiling point as branched chains
cannot pack as closely, this lowers the strength of intermolecular forces between molecules.

Density (Mass/Volume)
Density of Hydrocarbons are lower than water
• Dispersion Forces are the sole force found between the Hydrocarbon molecules
difficult for molecules to tightly pack as the force isn’t strong enough
• H2O molecules are found closer together due to the H-bonding present greater mass
present over a given volume

Density:
Alkynes> Alkenes > Alkanes

Solubility
Hydrocarbons are insoluble in polar solvents
- The only interaction that arises between hydrocarbons and a polar solvent in dispersion
forces
- To dissolve something – Ereleased (bond formation) > Erequired (bond breaking)
- Therefore, hydrocarbons cannot be dissolved the energy released from the formation of
dispersion forces is not sufficient enough to break the bonding in the H-bonding
between the H2O molecules and the dispersion forces between the Hydrocarbon
molecules

Solubility decreases with a longer carbon chain

- This occurs as the energy required in bond breaking increases whereas the energy
released in bond formation remains relatively the same

Hydrocarbons are soluble in non-polar solvents

- Dispersion forces between solvent molecules and between hydrocarbon molecules are
similar in strength to the dispersion forces between hydrocarbon and solvent molecules

Chemical Properties
Single covalent bonds are more stable than double or triple bonds
• Alkenes and Alkynes are more reactive than alkanes due to their unsaturated nature
which allows them to accept atoms to achieve saturation

Safely handling and disposing of organic substances

Syllabus Dot Point: Describe the procedures required to safely handle and dispose of organic
substances (ACSCH075)

Risk Solution
Volatility of many organic chemicals poses Working with volatile organic chemicals in a
the risk of inhalation or the absorption via fume cupboard or hood
skin
Flammability of organic chemicals which can Flammable and combustible organic
irritate skin and eyes compounds should be kept away from a
naked flame and never be heated on a hot

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 plate, instead they should be heated via a hot
water bath

• In addition to this, suitable PPE should be worn at all times

Environmental, economic and sociocultural implications of obtaining and using hydrocarbons

from the Earth
Syllabus Dot Point: examine the environmental, economic and sociocultural implications of
obtaining and using hydrocarbons from the Earth

• Hydrocarbons are derived from crude oil and natural gas

• Crude oil is a complex mixture of hydrocarbons which are sourced from decayed plant
or animal matter

Fractional distillation of crude oil

• Crude oil is boiled and is fed into a tower
• As the vapour moves up the tower, certain hydrocarbons condense into their liquids as
the temperature decreases

Fossil Fuels
- From decayed animal + plant matter

Advantages:
• Efficient fuel – High energy density (large energy output per unit combusted) Economic
• Production of fossil fuels results in job creation Economic
• Fossil fuels as a commodity contributes to an increased economic output Economic

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Disadvantages
• Non-renewable resource (rate of consumption > rate of production) – cannot sustain
long-term energy demands Economic + Social
• Increased contamination of crude oil results in a greater cost to purify it Economic
• Higher net release of greenhouse gases – contributes to a rising global temperature, thus
enhancing the effects of climate change. Additionally, greenhouse gases can be absorbed
into the oceans thus resulting in its acidification causing the disruption of fragile
ecosystems. Environmental

Transportation of fossil fuels poses many implications due to the risk of spills. A spill can lead
to:
• Long term damage to the ecosystems in the area Environmental
• Contamination of groundwater systems which feeds lakes and rivers Environmental
• Loss of income due to lost product Economic
• Large cost associated with the clean up Economic
• Lawsuits and legislative battles associated with the company Social

An alternative to fossil fuels are biofuels

Biofuel:
- Sourced from living matter (e.g. bioethanol (sourced from the fermentation of plant
material))

Advantages
• Renewable resource (rate of production > rate of consumption) – can sustain long term
energy use Economic
• Slows climate change – Burns more cleanly (less greenhouse gas emission) + the
photosynthesis of fuel crops consumes CO2 Environmental
• Production of biofuels can also be associated with Job creation Economic

Disadvantages
• Large areas of land required to grow fuel crops Less land available for food crops
not a viable option for countries that have scarce land available for agriculture Social
• Reduced energy density – releases less energy per unit combusted
• Most vehicle engines are incompatible with 100% biofuel – requires engine modification

IQ3: Products of Reactions Involving Hydrocarbons

Inquiry Question: What are the products of reactions of hydrocarbons and how do
they react?

Syllabus Dot Point:

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:
- Hydrogen (H2)

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 - Halogens (X2)
- Hydrogen Halides (HX)
- Water (H2O) (ACSCH136)

Combustion
Hydrocarbons can undergo complete combustion to form H 2O and CO2
- O2 has to be in excess

Complete combustion of ethane

C2H6 + (7/2)O2 2CO2 + 3H2O
Hydrocarbons can also undergo incomplete combustion which can form a mixture of H 2O, C
(soot), CO and/or CO2.
- O2 is the limiting reagent

Incomplete combustion of ethane

C2H6 + (5/2)O2 2CO + 3H2O

• Combustion is exothermic

Dehydrogenation of alkanes
• Reducing hydrogen atoms in alkanes
• Catalysts are required as alkanes are stable

Dehydrogenation of ethane
C2H6 C2H4 + H2

Addition Reactions

Hydrogenation:
• Hydrogen atoms are added across C=C or C≡C bonds
• Metal catalyst is needed
• Only works for unsaturated hydrocarbons

Hydrogenation of ethene

Halogenation
• Diatomic Halogen molecule adds across C=C

Chlorine Halogenation of ethene

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Hydrohalogenation
• Hydrogen halide (e.g. HBr) adds across C=C

Markovnikov’s rule
- If alkene is asymmetrical, two products are possible
- Major product occurs when the hydrogen atom attaches to the carbon containing more
initial hydrogen atoms

Hydrohalogenation of ethene with HBr

Hydration
• Water adds across C=C
• Alcohol is formed
• Dilute H2SO4 or Dilute H3PO4 is used
• Strong acids act as a dehydrating agent and thus will negate the reaction
• Markovnikov’s rule is used to determine the major product

Hydration of ethene

Bromine water test

- Can be used to test for unsaturation

Br2 is orange/red in colour – when reacted with a alkene/alkyne it can form the colourless
bromo-alkane while simultaneously decreasing [Br2] results in the fading of the orange/red
colour.

Saturated hydrocarbons cannot react with Br2

Therefore:
- If coloured solution fades unsaturated compound present

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 - If coloured solution remains the same saturated compound present

Conditions for the test:

- UV light must be excluded

If UV light is present – bond between bromine atoms can break to form radicals radicals can
react with both unsaturated and saturated compounds thus negating the purpose of the test as
both compounds will decolour the bromine water

Substitution reactions
Syllabus Dot Point: Investigate, write equations, and construct models to represent the reactions
of saturated hydrocarbons when substituted with halogens

- Alkanes undergo substitution reactions with halogens to produce haloalkanes

- Due to the strong C-H bond, light is needed for the reaction to occur
- Substitution reactions can continue until all H’s are substituted

Stepwise Chlorine substitution of methane

How substitution reactions occur:

Example: Reaction between chlorine and methane
- In the presence of UV light, chlorine can form free radicals – Cl2 2Cl•

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 - The Cl• is reactive and when it collides with a methane molecule it will combine with a
hydrogen atom to produce a methyl free radical - Cl• + CH4 HCl + CH3•
- This methyl free radical will react with a Cl2 radical to form a C-Cl bond CH3• + Cl2
CH3Cl + Cl•
- The formation of another chlorine radical allows for the continual substitution of the
alkane

IQ4: Alcohols
Inquiry Question: How can alcohols be produced and what are their properties

Alcohol: an alkane in which one or more hydrogen atoms have been replaced by an -OH
functional group

Types of alcohols:
Syllabus Dot Point:
Investigate the structural formulae, properties and functional group including:
- Primary
- Secondary
- Tertiary alcohols

Primary Alcohol:
The carbon holding the hydroxyl group is bonded to 1 alkyl group

Example:

Secondary Alcohol:
The carbon holding the hydroxyl group is bonded to 2 alkyl groups

Example:

Tertiary Alcohol:
The carbon holding the hydroxyl group is bonded to 3 alkyl groups

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Example:

Boiling Points:
Syllabus Dot Point: Explain the properties within and between the homologous series of
alcohols with reference to the intermolecular and intramolecular bonding present – Boiling
Points

• Alcohols are polar due to the polar -OH functional group formation of H-bonds
between molecules

As the length of the parent chain increases, the boiling point increases
• More electrons present as the chain increases stronger and more frequent dispersion
forces more energy required to break the intermolecular bonds

BPprimary > BPsecondary > BPtertiary

Greater exposure of the hydroxyl group a greater chance the molecule will form H-bonds

Solubility in water
Syllabus Dot Point: Explain the properties within and between the homologous series of
alcohols with reference to the intermolecular and intramolecular bonding present – Solubility

• Alchols are polar greater likelihood to be soluble in water compared to hydrocarbons

Small alcohols are fully soluble in water

- Main intermolecular force formed = H-bond
- To be soluble Ereleased > Erequired
- H-bonds are formed, and H-bonds are also required to be broken, therefore the energies
associated with bond formation and bond breaking are similar in quantity Alcohol is
allowed to dissolve

As length of parent chain increases, solubility decreases

- Significant non-polar alkyl region + Small polar hydroxyl region
- Therefore, when added to water, the alcohol is more likely to form dispersion forces
- Source of energy released in bond formation comes from dispersion forces results in
an insufficient energy output to break the H-bonds between water molecules

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Practical Investigation
Syllabus Dot Point: conduct a practical investigation to measure and reliably compare the
enthalpy of combustion for a range of alcohols

- Determining heat of enthalpy from ethanol

Ethanol is burnt (energy released) water is heated (energy absorbed)

qreleased = -qabsorbed

therefore:
n•∆H•(1-%heat loss) = -m•Cw•∆T

n = number of moles of fuel combusted

∆H = molar heat of combustion
m = mass of water
Cw = heat capacity of water
∆T = change in temperature of water

Molar heat of combustion

- Heat released by complete combustion of 1.0 mole of fuel

Sources of error

Error Minimisation
Heat loss: - Use of lid
- From surface of water - Use of Styrofoam cup which is better
- Conduction by metal can at retaining heat
- Between flame and can - Use of draft shield
Incomplete combustion Reacting fuel with a pure oxygen supply to
- O2 can be limiting reagent ensure complete combustion

Reaction of alcohols
Syllabus Dot Point:

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Write equations, state conditions and predict products to represent the reactions of alcohols,
including but not limited to (ACSCH128, ACSCH136):
- Combustion
- Dehydration
- Substitution with HX
- Oxidation

Combustion of alcohols:
• Complete combustion produces CO2 and H2O
• Incomplete combustion forms a mixture of C, CO, CO 2 and/or H2O

Combustion of ethanol

Substitution with hydrogen halides

- Halogen replaces -OH Forms haloalkane & water

Substitution of ethanol with HCl where Markovnikov major and minor product are present

Dehydration of alcohols:
- Removes -OH and H from adjacent C
- Heat is required
- Concentrated acid (e.g. H2SO4) is used as a catalyst and dehydrating agent
- Double C=C bond is formed
- Major product favours the compound with more alkyl groups on either side of the
carbon (Zaitsev’s rule)

Dehydration of ethanol

Oxidation of alcohols
• C-H bond is broken, C-O bond is formed

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 • Heat is required in the reaction

Oxidising agents
• Acidified potassium dichromate (K2Cr2O7) Cr6+ (orange) reduces into Cr3+ (green) –
Cr2O72-(aq) + 14H+(aq) + 5e- 2Cr3+(aq) + 7H2O(l)
• Acidified potassium permanganate (KMnO4) Mn7+ (purple) reduces into Mn2+
(colourless) – MnO4- (aq) + 8H+(aq) +6e- Mn2+(aq) + 4H2O(l)

Oxidation of primary alcohols:

Primary Alcohol Aldehyde Carboxylic Acid

Oxidation of ethanol – [O] represents the oxidising agent

To favour production of aldehyde:

- Alcohol in excess
- Low temperature
- Distil aldehyde from reaction

To favour production of acid

- Excess oxidising agent
- High temperature
- Heat under reflux to prevent the loss of aldehyde

Heat under reflux apparatus

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Oxidation of secondary alcohols:
Secondary Alcohol Ketone

Like the oxidation of primary alcohols

- C-H bond is broken, C-O bond is formed
- Acidified KMnO4 or Acidified K2Cr2O7 is used

Oxidation of propan-2-ol where [O] is the oxidising agent

• Tertiary alcohols cannot oxidise as there is no C-H bond to break

How to test for tertiary alcohols

1. Add acidified KMnO4 (purple) & alcohol to test-tube
2. Heat test-tube in water bath
3. Observe for colour change, if the colour of solution remains the same, a tertiary alcohol
is present

How to distinguish between primary and secondary alcohols

1. Oxidise alcohol to aldehyde or ketone
2. Add Benedict solution (contains Cu2+ ) to test-tube
3. Heat test-tube in water bath
4. Observe for colour change – turns red for aldehyde/stays blue for ketone

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Production of Alcohols
Syllabus Dot Point:
Investigate the production of alcohols including:
- Substitution reactions of halogenated organic compounds
- Fermentation

Substitution of haloalkanes
- Haloalkane undergoes substitution with water or strong base

For water:
- Dilute acid catalyst
- Heat under reflux

• Solvent is a 50/50 mixture of alkanol & water

• Tertiary haloalkanes are the most reactive – halogen able to pull more electrons toward it
making it more electronegative

Substitution of chloroethane with water

Substitution of bromoethane with KOH

Hydration of alkenes
• React alkene with steam (Dilute acid catalyst present)
• 5% of alkene is converted each time – remove alkanol and recycle alkene until 95%
conversion is achieved

Hydration of ethene

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Pros of hydration:
- Pure product (no-by products)
- Faster production

Cons of hydration
- High temp (300ºC) and high pressure (60-70 atm) required expensive + safety risk
present
- Uses petrochemicals sourced from crude oil non-renewable as there is a finite
resource of petrochemicals

Fermentation (only applies to ethanol)

1. Extract complex carbohydrates (e.g. starch) from plant material
- Heat plant material with hot water
- Warm with malt – contains enzymes that decompose starch into disaccharides

2. Add yeast
Enzymes in yeast decompose disaccharides into simple sugars which is then fermented

For fermentation to occur:

- Anaerobic environment is present (no O2 – prevents oxygen from oxidising ethanol)
- 25-40ºC, pH = 6.1-6.8 – otherwise the enzymes in yeast denature
- Maintain ethanol concentration at 14%v/v – prevents yeast poisoning

3. Separate ethanol from mixture via fractional distillation

- Obtains 96% ethanol

Fermentation of glucose sourced from starch

Pros of fermentation
- Based on renewable sources
- Gentle temp & atmospheric pressure (1 atm) – cost effective + low safety risk

Cons of fermentation
- Slow process
- Cannot produce 100% ethanol

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Compare and contrast fuels from organic sources to biofuels, including ethanol
Syllabus Dot Point: Compare and contrast fuels from organic sources to biofuels, including
ethanol

• Crude oil is the main organic source of fuels, other sources may include coal and natural
gas
• These fuel sources are non-renewable in nature
• These fuel sources also output greenhouse gases thus accentuating the effects of climate
change

Bioethanol
• Produced from the fermentation of food crops such as wheat

Pros:
- Ethanol combusts more readily and will release less carbon dioxide than fossil fuels
- Ethanol can be added to existing fuels in small amounts without needing a change in the
engine (e.g. E10 is a petrol blend with 10% ethanol)

Cons:
- Leads to the clearing of large amounts of land which cannot be used for food
- Requires large amounts of water – can divert water from food growing crops
- The production of bioethanol is a contestable topic in the modern world as it acts as an
obstacle for the prevention of hunger/poverty due to the fact that it blockades food
production on the designated area
- Ethanol absorbs moisture from the air and thus it is difficult to store and cannot be
transported through existing fuel pipelines
- Lower energy density when compared to petrol

Biodiesel
• Created from the transesterification of a vegetable oil or animal fat

Pros:
- Can be produced from waste products in agriculture – renewable resource
- Similar fuel efficiency when compared to other fuels
- Produces a less net carbon emission compared to regular diesel

IQ5: Reactions of Organic Acids and Bases

Inquiry Question: What are the properties of organic acids and bases

Syllabus Dot Point:

Invetigate the structural formulae, properties and functional group including:
- Primary, secondary and tertiary alcohols
- Aldehydes and ketones
- Amines and amides
- Carboxylic acids

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Structural formulae, properties, and functional group of primary, secondary and tertiary
alcohols (Revision)

Oxidising Alcohols:
- Primary Aldehyde Carboxylic Acid
- Secondary Ketone

• Two -H atoms change to ions: 2(-H) 2H++ 2e-

• C-O bond is added from the oxidising agent

To favour production of the aldehyde

- Oxidising agent is a limiting reagent
- Distil off aldehyde immediately
- Low heat

To favour production of the carboxylic acid

- Oxidising agent in excess
- Heat under reflux

Oxidation of aldehydes:

Acidified potassium dichromate (VI) solution can be used to distinguish between aldehyde &
ketone
- Ketone: no colour change in orange solution
- Aldehyde: orange solution transitions to green

Structural formulae, properties and functional group of amines and amides

Amides:
• Derived from carboxylic acids
• A carboxylic acid contains the -COOH group, and in an amide, the -OH part of that
group is replaced by the -NH2 group.

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 • Amides are characterised by the presence of the =O and N

Properties of amides:
Melting point:
• High melting point due to the formation of hydrogen bonding

As the length of the parent chain increases, MP/BP increases

- More atoms more e- increased size of temporary dipoles stronger + more
frequent DF increased MP/BP

BP/MPstraight chain amides > BP/MPbranched amides

- Straight chain amides compact more easily intermolecular forces form over a shorter
distance stronger DF increased MP/BP

Solubility in water

Small amides are soluble in water

- Strong H-bonds between amide & water Ereleased (bond fornation) > Erequired (bond breaking)

As length of parent chain increases, solubility in water decreases

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 - Main interaction with water is in dispersion forces as majority of surface contact is in the
non-polar alkyl region less energy is released as DF are low energy bonds Strong
H-bonding present between water molecules Ereleased (bond fornation) < Erequired (bond breaking)
compound is insoluble

Amines
- Contains amino functional group
- Characterised by the presence of N
- Nitrogen can only make 3 bonds

1. Primary Amines
• N bonded to 1 alkyl group

Example: Propanamine/propan-1-amine/1-aminopropane

2. Secondary Amines
• N bonded to 2 alkyl groups

Example: N-methylethanamine

3. Teritary Amines

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 • N bonded to 3 alkyl groups

Example: Trimethylamine

BP/MP of amines
As chain length increases, BP increases
- More atoms more e- increased size of temporary dipoles stronger + more
frequent DF increased MP/BP

BP/MPprimary > BP/MPsecondary > BP/MPtertiary

- Tertiary amines cannot form H-bonding – there is no -H that is bonded to F, O or N
- For (BP/MPprimary > BP/MPsecondary ) – electronegativity difference is smaller between C
and N than H and N N is less electronegative in secondary amine smaller
permanent dipole weaker H-bond

Solubility in water
Tertiary amines are insoluble
- Cannot form H-bonding in water – no -H bonded to F, O or N

As length of parent chain increases, solubility decreases

- Main interaction with water = DF DF is low energy insufficient energy to break the
strong H-bonding between water molecules

Esters
Syllabus Dot Point: Investigate the production, in a school laboratory of simple esters

• Formed when the hydrogen in the -COOH group of a carboxylic acid is replaced by an
alkyl group
• Formed when an Alcohol and Carboxylic Acid react

Example: Esterification between Ethanoic Acid and Propanol

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Concentrated H2SO4 is used in Esterification
- Substance is a good dehydrating agent due to its high affinity for water can
continuously absorb the H2O and decrease its presence in the system Equilibrium will
be shifted to the right (LCP) to favour the production of the Ester

Uses of Esters:
- Perfumes
- Food additives

Naming Esters:
The names for Esters are comprised of two parts

Part 1: Alcohol
The -anol suffix of the alcohol is changed to an -yl suffix
e.g. butanol => butyl, propanol => propyl

Part 2: Acid
The -oic acid suffix of the carboxylic acid is changed to an -oate suffix
e.g. butanoic acid => butanoate, propanoic acid => propanoate

Functional Group of Ester

• The C=O and C-O bonds in the Ester make them polar substances due to the presence
of dipole-dipole bonding
• Lower boiling point than alcohols and carboxylic acids

Esters are immiscible with water and have a lower density than water:
- Large portion of molecule is the non-polar alkyl region lack of h-bonding in esters
means its insufficient to break the h-bonds present in water

Esterification:
Type of condensation reaction (expelling a small molecule
- Contains 2 molecules (alcohol + acid), expells the small molecule of water

Overcoming constraints/limitations
Constraint Minimisation
Slow reaction rate - Catalyst (conc. H2SO4)
- High temp

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 Equilibrium reaction doesn’t reach H2SO4 acts as a dehydrating agent which
completion shifts the equilibrium to the right maximising
ester production
Volatile components – Alcohol + Ester Use of reflux setup which prevents the loss of
- Will evaporate under heat reactants

Procedure for Esterification:

1. Setup a hot-plate & reflux equipment
2. Pour 10mL of 0.5molL-1 pentan-1-ol into a round bottom flask & add 20mL of
concentrated ethanoic acid
3. Add 1mL of conc. H2SO4 & boiling chips to mixture
4. Heat under reflux for 45 minutes
5. Allow mixture to cool and transfer contents to a separating funnel

Isolation of Ester
• Final mixture of organic and inorganic substances
• Separating funnel isolates immiscible layers

Ester + pentan-1-ol = organic phase/non-polar

- React pentan-1-ol as limiting reagent otherwise distillation is required

H2SO4 + acetic acid = aqueous phase

- Aqueous phase is denser and will run out when stop-cock is opened

1. Wash mixture with water twice (10mL)

- Separates mixture into organic & aqueous phase
- Add 1-2 drops of water – check which layer it dissolves in as a confirmatory test
- Discard aqueous layer

2. Wash mixture with weak base (e.g. Na2CO3)

- Acid reacts with carbonate
- Forms carboxylate ion & CO2 – wash mixture with water and discard aqueous layer

3. Remaining mixture is the organic layer – wet ester

- Treat mixture with water – Anhydrous power (e.g . BaSO4)

Risk Assessment
Risk Minimisation
Volatility of Acid and Alcohol - Use of a water-cooled condenser to
prevent escape of volatile vapours
- Experiment is performed in a fume
cupboard or well-ventilated area
Corrosiveness of Organic Acid and H2SO4 - Avoid direct contact with chemicals
catalyst - Have access to running water to flush
skin
Flammability of Alcohol - Avoid heating with naked flame
- Use heating mantle

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Explain the properties within and between the homologous series of carboxylic acids, amines,
and amides
Syllabus Dot Point: explain the properties within and between the homologous series of
carboxylic acids amines and amides with reference to the intermolecular and intramolecular
bonding present

BP/MP
Carboxylic Acids forms dimer structure
- Extreme permanent dipole established from the presence of 2 H-bonds between C=O
and O-H
-
Dimer Structure

Carboxylic Acids have lower Boiling Points than amides

- Amides can form more extensive H-bonding

Amides: production and properties

Making amides from carboxylic acids

1. Carboxylic Acid is converted into an ammonium salt with excess acid
2CH3COOH + (NH4)CO3 2CH3COOHNH4 + H2O + CO2

2. The mixture is then heated and the salt dehydrates to produce ethanamide
CH3COOHNH CH3CONH2 + H2O

Amides can be reduced to primary amines

CH3CONH2 + 4[H] CH3CH2NH2 + H2O

Amines are stronger bases than ammonia and the equilibrium position is more to the right
greater ionisation

Soaps and Detergents

Syllabus Dot Point: Investigate the structure and action of soaps and detergents

Saponification reaction
Reaction involving an ester (in the form of a fat/oil) and a basic solution

Example:
Methyl octadecenoate + Sodium Hydroxide Sodium + Methanol octadecenoate

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 • Fats and oils are Esters of glycerol where ONE alcohol glycerol molecule is combined
with THREE fatty acid (long chain carboxylic acids) molecules
• The difference between fats and oils is that fats are saturated (single C-C bonds) whereas
oils are unsaturated (at least one double C=C bond present)

Esterification of glycerol and three fatty acid molecules to produce a saturated fat

• There is a polar region in the ester linkage and there is a non-polar region in the tail of
the molecule

Saponification:

Fat/Oil + Base Glycerol + Salt

• The salt formed in the reaction is the soap

• The purpose of soaps is to act as a bridge which allows for immiscible substances to
dissolve

Structure of a soap

• The soap has an anionic, polar head which attracts water

• The soap has a non-polar tail which attracts the non-polar grease (like dissolves like)

Cleaning Action – Action of Surfactants

Surfactant – a substance that decreases the surface tension of water and disperses dirt and grease
as small particles throughout water; soaps and detergents act as surfactants

When soap is dissolved in water

- It dissociates into its ions
- Anions accumulate at surface polar heads in water, non-polar tails out of water

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 - Reduces surface tension

When soapy water contacts oil or grease:

- The non-polar tails forms dispersion forces and embeds into the grease
- The polar heads form dipole-dipole forces with the water and exist on the outside
surface of the oil

When the solution is agitated (e.g. scrubbing)

- Grease is lifted off the surface
- Soap molecules/surfactant ions surround the grease to form micelles

Anionic heads repel each other

- Grease droplets are suspended in emulsion
- Grease can no longer aggregate

Detergents:
- Detergents also have a hydrophilic head and a hydrophobic tail

In detergents, the head may be

- Anionic ammonium head
- Cationic sulfonate head
- Non-Ionic peroxide head

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 • In hard water, the carboxylate ion in soap will precipitate with the Ca2+ and Mg2+
forms scum
• Results in less surfactant molecules which are available to form micelles less effective
cleaning

2RCOO- + Ca2+ 2(RCOO)2Ca

Detergents effectively clean in hard water as they cannot precipitate with the ions
- Cationic heads have a positive charge and thus cannot precipitate with other positively
charged ions
- Anionic heads are soluble with hard water ions
- Non-ionic has no charge

Uses of Detergents
• Anionic is a stronger cleaning agent used for dish soap
o Benzene ring can form stronger dispersion forces with grease
o Forms large amounts of foam
• Cationic is used for shampoos and hair conditioners
o Positively charged prevents the tangling of hair
o Biocidal kills bacteria
• Non-ionic forms low amounts of foam
o Used for cosmetics and paints

Organic Acids’ and Organic Bases’

Syllabus Dot Point: Investigate the differences between an organic acid and organic base

Organic Acid
- Contains a carboxyl (-COOH) group
- Donates a proton to water
- Reacts with metals to produce salt and hydrogen gas
- Can undergo neutralisation with a base

Organic Base
- Contains an amino (-NH2) group
- Accepts a proton from water
- Cannot react with metals
- Undergoes neutralisation with acid
- Are stronger bases than ammonia; electronegative nitrogen attracts electron density of
alkyl group towards itself more negatively charged gains protons more easily

IQ6: Polymers
Inquiry Question: What are the properties and uses of polymers?

Polymerisation: process of forming polymers

- Many identical molecules (monomers) combine to form 1 large polymer molecule

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Addition polymerisation:
Syllabus Dot Point: Model and compare the structure, properties and uses of addition polymers
of ethylene and related monomers, for example:
- Polyethylene (PE)
- Polyvinyl Chloride (PVC)
- Polystyrene (PS)
- Polytetrafluoroethylene (PTFE)

• Unsaturated monomers join together to form an addition polymer

Characteristics of addition polymerisation:

- Reactive C=C opens up & bonds covalently to the next monomer (catenation)
- Does not produce by products

Example: Polyethylene

Production of addition polymers:

Stage 1: Initiation
• Initiator molecule (e.g. hydrogen peroxide) splits into 2 radicals

R-O-O-R 2R-O•

• Monomer reacts with radical forms new radical

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Stage 2: Propagation
• New Radical reacts with monomer
i) Double bond of monomer opens up
ii) Bonds covalently to next monomer long polymer chain starts to be
established
• Reaction can continuously occur

Stage 3: Termination
• 2 of the long propagating polymer chains react forms a covalent bond and a
completed polymer chain
• Or the long propagating polymer chain reacts with a left-over free radical forms a
covalent bond and a completed polymer chain

Polyethylene (PE)

Monomer: Ethene/Ethylene – CH2=CH2

Two types of PE:
- High Density Polyethylene (HDPE) => closely packed polymer chains
- Low Density Polyethylene (LDPE) => loosely packed polymer chains

LDPE:

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 • Formed under high temperatures and pressures 300ºC + 2000atm => less controlled
environment results in a less structured polyethylene

Properties
- Extensively branched chains
i) Loosely packed – more amorphous regions – no clear and defined structure
ii) Low density – softer and more flexible
- Lower melting points
i) Reduced packing of chains – weaker dispersion forces

Uses of LDPE:
- Plastic bags
- Squeeze bottles
- Cling wrap

HDPE:

• Formed under low temperatures and pressures 60ºC + 5atm => stable environment
results in a more structured polyethylene
• Ziegler-Natta catalyst used => more controlled

Properties:
- Unbranched straight chains
i) Tightly packed more crystalline regions
ii) High density hard and less flexible
- Higher melting points
i) Greater compaction stronger dispersion forces

Uses of HDPE:
- Petrol tanks
- Buckets

Polyvinyl Chloride (PVC)

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Monomer: Chloroethene/Vinyl Chloride – CH2=CHCl

Properties:
- Large Cl atoms along chain stiffens chain
i) Hard, brittle & rigid
- Higher melting point than PE
i) Polar covalent C-Cl bond dipole-dipole forces
ii) Stronger attraction between chains
- Specialised properties by incorporating various additives
i) Add flame retardants less flammable
ii) Add UV absorbers prevent UV decomposition

Uses of PVC:
- Shower curtains
- Covering of electrical wires
- Credit cards

Polystyrene (PS)

Monomer: phenylethane/styrene
2 Different forms of polystyrene:
- Crystal polystyrene
- Expanded polystyrene

Crystal Polystyrene:

Properties:
- Large Phenyl rings along chain stiffens chain
i) Material is hard, brittle & rigid
- Low melting points only dispersion forces present

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 - Reduced compaction material is transparent

Uses of Crystal Polystyrene

- Screwdriver handles
- CD cases

Expanded Polystyrene:

Production: Gases blown through molten polystyrene

Properties:
- Good heat and sound insulator
- Absorbs impact well

Uses:
- Packaging foam
- Foam cups

Polytetrafluoroethylene (PTFE)

Monomer: Tetrafluoroethylene – CF2=CF2

Properties:
- Helical structure of chains close packing high melting points
i) Thermally stable between -200ºC to +260ºC
ii) Chemically inert
- Highly insoluble in most solvents
- Low friction coefficient non-stick surface
- High flexural strength good at bending
- High density

Uses:
- Non-stick frying pans
- High grade electrical insulation
- Medical implants

Condensation Polymerisation
Syllabus Dot Point: Model and compare the structure, properties and uses of condensation
polymers, for example:
- Nylon
- Polyesters

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 • Polymers formed by the elimination of a small molecule when pairs of monomer
molecules join together
• Produces by-products => loses atoms
• Monomers must have functional groups on both ends in order for small molecules to be
expelled

Nylon
Monomer: Nylon-6 = 6-aminohexanoic acid

The -O-H from the carboxylic acid and the -H from the amine combine to form an
amide/peptide linkage

Addition of dilute acid to nylon

- Nylon attacked with dilute acid Acid adds water to the amide links – adding water to
reform the original acid and amine groups the polymer chains break down into its
initial small individual molecules and the structure is damaged

Properties of nylon:
- High melting point
- Good weathering properties
- Soft feel
- Resistance to colour fading
- Excellent abrasion resistance

Uses of nylon
- Clothing
- Parachutes
- Umbrellas

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Polyesters
- Formed by reacting an acid with two carboxyl groups and an alcohol with two hydroxyl
groups

Example: Polymerisation of benzene-1,4-dicarboxylic acid and ethene-1,2-diol

Ester linkage present

Simple esters are hydrolysed by reaction with dilute acid or alkalis

- If dilute acid or alkali is spilt on a fabric made from polyester, the ester linkages will
break the initial carboxylic acid and alcohol molecules are formed The polymer
structure is destroyed

Properties of polyester
- Fabrics and fibres are extremely strong
- Durable; resistance to most chemicals, stretching, shrinking and abrasion
- Polyester is hydrophobic
- Retains its shape

Uses of polyester
- Clothes
- Ropes
- Home furnishings

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