Hydrocarbons

Inquiry question: How can hydrocarbons be classified based on their

structure and reactivity?

Hydrocarbons are used throughout society. Fractional distillation of petroleum is the main
source of hydrocarbons. They are used as fuels to power machines and vehicles as well as in
the production of a wide variety of organic chemicals, solvents and plastics. However, can lead
to environmental pollution.

Models Of Hydrocarbons

Alkanes: Saturated Hydrocarbons,

● all alkanes are pretty unreactive.

● Branched alkanes have lower boiling points than unbranched alkanes with similar molar
masses. This is because their branching reduces their ability to pack in tightly, which
results in weaker dispersion forces compared to unbranched alkanes which can pack
closely together.

Alkenes: unsaturated hydrocarbons

Alkynes: unsaturated hydrocarbons

● Structural formulas are used to show the differences in bonding homologous series.
● Structural formulas are used to show the differences in bonding angles of the
three-dimensional molecules
● In tetreheradal ( 109 28')
 ●
● Structural formulas of alkenes

Condensed structural formulas can also be used to show the arrangement of atoms in
hydrocarbons

● Pentene
● Pent-1-ene
● Pent-1-yne

Molecular shapes
Hybridisation of Orbitals in Hydrocarbons

● Orbitals have variable shapes in three dimensions. A maximum of 2 electrons can

occupy an orbital.
● A maximum of 2 electrons occupy an orbital.
 ● Hybridisation: a procedure used in the valence bond theory in which atomic orbitals are
combined to produce molecular orbitals

Intermolecular and intramolecular bonding

Physical properties of Hydrocarbons
● Hydrocarbons are nonpolar molecules
● Intermolecular forces between these molecules are dispersion forces caused by
interaction of temporary dipoles and induced dipoles.
● These forces are much weaker than the intramolecular forces.
● Inter- means attractive forces between molecules
● Intra-means covalent bonds joining atoms together on the molecule
 ● Melting and boiling points of hydrocarbons increase as the molecular weight of
the molecules increases.
● The longer the hydrocarbon chains, the stronger the dispersion forces that attract
neighboring molecules.
● Shapes of the hydrocarbon molecules affects the strength of the dispersion
forces
● The presence of double or triple bonds changes the shape of dispersion forces
● Hydrocarbon isomers vary melting and boiling points. Mainly due to differences in
shape of the molecules.
● Because hydrocarbons are nonpolar they do not dissolve in water but readily
dissolve in organic solvents such as benzene ( C6H6).
● The dissolution process involves dispersion interactions between solute and
solvent molecules and is driven by an entropy increase
●

Safety in handling and disposal of organic substances

Volatility and flammability
● The weak intermolecular forces between hydrocarbons molecules of low molecular
weight male them highly volatile substances. Eg. a closed container becomes filled
rapidly with its vapour
● Higher the ambient temperature the higher the volatility. This property makes many
alkanes useful fuels for internal combustion engines.
● Equilibrium vapour pressure is a measure of volatility.
● The lower the molecular weight of a carbon, greater its volatility
● For example,short chain alkanes have weaker dispersion forces between its molecules.
Safety issues
 ● Flash point means the lowest temperature at which vapour pressure of the
substance is just sufficient to form a combustible mixture of the vapour with aire
flames or sparks can then ignite this combustible mixture.
● Petrol has a flash point of -43 degrees celsius this very low flash point means
that combustible air/petrol vapour mixtures will form even in very cold
environments
● Kerosene has a higher flash point not form under standard temperatures. Flash
point increases with increasing molecular weight. (48C)
● High molecular weight alkanes lower volatility and flash point safer to store
● Different hydrocarbon compositions in the fuel fractions will alter the flash point.
● Fractions: mixtures of hydrocarbons with a specific boiling point range that are
produced by fractional distillation of petroleum
Questions
Explain why boiling points of alkanes increase with increasing molecular weight.
The longer the alkane gets (higher molecular weight), the more intermolecular forces are
present (London Dispersion), and this increases the melting and boiling points.

Implications of Using Hydrocarbons as Fuels

● Obtaining and using hydrocarbons has several disadvantages.
● But we rely on them as our primary source of fuel to power our daily lives.
● Environmental impacts are extremely negative and include:
● Oil spills
● Land clearing
● And, the release of emissions and hazardous waste.
● Economic impacts are mostly positive and include:
● Job opportunities and income
● Funding for local infrastructure
● And, personal investment opportunities.
● Sociocultural impacts are also negative, including:
● Increased instances of respiratory illness
● And, the destruction of culturally significant artefacts and heritage sites.

Obtaining and Using Hydrocarbons

Sources production and uses of hydrocarbons
● Majority of hydrocarbons extracted from organic sources such as petroleum and natural
gas located in geological structures
 ● Petroleum deposits vary in the amounts of natural hydrocarbon gases. Methane is
typicaling about 89%
● Crude oil fractional distillation separates the hydrocarbon mixture according to
differences in boiling points.
● Components of crude oil are too numerous to extract and separate
● Thus, they are separated into fractions containing mixtures of various hydrocarbons.
● Physical separation is performed in a steel fractionating column and is based on the
boiling point ranges for each fraction.
● The higher the boiling point range, the greater the proportion of high molecular weight
hydrocarbons fractions
● Fractionating process is carried out…..
● Crude oil is formed from anaerobic decay of dead plankton and algae in subterranean
geological structures.
● Boiling points are used to separate from fractions
● Crude oil distillation fractions are gasoline, diesel, petrol, refinery gas and naphtha
● Heavier fractions undergo further to break up longer chains into shorter chains suitable
for petrol.
● For example C16H34 diesel oil fraction can catalytically cracked 500 C degrees to for
heptane ..
● Kerosene fraction (C11-C16)
● Petrol Fractions ( C5-C8)
● Diesel Oil ( C15-C18)
● Higher molar mass hydrocarbons have higher boiling points due to greater dispersion
forces between their molecules. Therefore the lighter hydrocarbons boil first and their
vapours rise up the fractionating tower.

Economic, Environmental and Sociocultural Issues

Petroleum products provide Australia and other nations with compounds for
- Transport
- Heating
- Plastic Productions
- Lubrication greases

● The economics of petroleum producing countries significantly supported sale of

petroleum products other countries
● Petroleum mining environmental pollution when accidents have occurred
● One of the major disadvantages of fossil fuels is the combustion of large amounts of
carbon dioxide produced.
● Equation shows production carbon dioxide when octane undergoes complete
combustion
● Hydrocarbons release considerable amounts energy on combustible
● Petroleum mining has led environmental pollution accidents have occurred
●
 Products of Reactions Involving Hydrocarbons
Inquiry Question: What are the products of reactions of hydrocarbons and how do they
react?
Hydrocarbons are import in our daily lives. Chemists have investigated the chemical properties
of hydrocarbons over many centuries and new compounds have been produced based on this
knowledge. Compounds j formed from petroleum are called petrochemical and the the
properties of the products that form them.

Hydrocarbon Reactions
Additions Reactions : a reaction between an unsaturated hydrocarbon and another molecule to
form a new product

● Unsaturated hydrocarbons have reactive double or triple bonds

● Bonds have high electro negative density property promotes reactions with other
molecules such as halogens that have high electronegativity
● Unsaturated hydrocarbons readily react by addition reactions in which alkene or alkyne
combines with another molecule to form one product

Halogen addition reactions

Alkenes and Alkynes readily react with halogens such as chlorine via addition reactions where
halogens such as chlorine via addition reactions double or triple bonds break. Chlorinated
alkanes are products:
Bromine Stuff

● Various qualitative tests can identify unknown organic compounds using reactions that
are specific functional compounds.
● Unsaturated hydrocarbons can be distinguished from alkanes using the bromine water
test.
● Pure bromine is a toxic, red brown fuming liquid.
● Bromine water is a solution of bromine in water.
● The colour of bromine water depends on the degree of dilution.
● Very from orange brown to orange or yellow
● More dilute solution the safer it is to use
● Bromine water contains bromine molecules and hypobromous acid molecules.
● The double bond in the hex-1-ene reacts with these molecules via additional reactions
breaking the double bond.
● HOBR is colourless so addition reaction does not result in colour change
COME BACK TO THIS
Types of reactions
Addition reaction ( alkene)
● Joining two or more molecules to form a larger molecule
● Unsaturated molecule + another molecule => larger molecule
● Readily undergo addition reaction
Halogenation
● Adding a halogen molecule to an alkene to form a haloalkane
● Halogens can be added to alkene by breaking the double bonds are called haloalkane
● Alkene + halogen > dihaloalkane
Hydrogenation
● Adding hydrogen molecule to an alkene to form an alkane
● Alkene + hydrogen > Alkane
Hydration
● Adding water molecule to form an alcohol
● Requires dilute sulfuric acid
● Ethene + Water > Alcohol
Hydration
● Adding a hydrogen halide molecule to form a haloalkane
● Ethene + Hydrogen bromide > Bromethane
Addition reaction ( alkyne)
Hydrogenation
- Needs a platinum catalyst turns an alkyne into an alkene then quickly into an alkane
- Lindlar catalyst to get alkene
Hydrogenation
- Need HgSo4 and dilute H2SO4
- Products aldehyde only for ethyne
- Ketone mostly produced
Hydrohalogenation of Alkynes
- No catalyst is need
- If the hydrogen halide is not added in excess an alkene will form
Condensation
When a small molecule is lost in the formation of a larger molecule and a new carbon to
carbon bond is formed

Elimination
Removing a small group of atoms from a larger molecule

Substitution
Replacing one species on a molecule with another the thing that is put in is subbed with the
thing that has been put out

Polymerisation
Joining many simple molecules to form a giant molecule

Oxidation
When a species loses electrons

Reduction
When a species gain electrons

Markovnikov’s Rule
● The rule states that in an alkene addition reaction with hydrogen halide
● The proton (H) is attached to the carbon atom with more hydrogen substituents
 ● The halogen( X) is attached to the carbon atoms with more carbon substituents in the
major product
Atomi
● Markovnikov's rule states that when a compound of the form HX is added to an
asymmetrical alkene, the hydrogen becomes attached to the carbon with more
hydrogens already attached to it.
○ An asymmetrical alkene does not have the carbon-carbon double bond in the
centre. This means the carbon atoms in the double bond are joined to different
atoms or groups.
○ Markovnikov's rule is not as relevant for symmetrical alkenes, where the products
of the addition reaction are the same.
● The major product of an addition reaction involving an asymmetrical alkene is the
molecule that preferentially forms based on Markovnikov's rule.
● On the other hand, the minor product is the molecule that does not form as often.

Introduction to Alcohols
The basics
● A homologous series with a hydroxyl (-oh)
● Polar molecules due to polar carbon to oxygen hydrogen bond
● The polar bond determines what king of reactions alcohols can get involved in
The Classifying Alcohols
Primary - bonded to methyl group
Secondary - bonded to 2 methyl group
Tertiary - bonded to 3 methyl group

Properties of Alcohols

Boiling point of alcohols

● The boiling point of a substance depends on how much energy is needed to break the
intermolecular bonds.
● Hydrogen bonds and dipole-dipole forces are much stronger than dispersion forces so
much more energy is needed to break the bonds between molecules of alcohols so they
have higher boiling points than alkanes
● BP increases with the number of carbons
● Dispersion forces become stronger as the size of the molecule increases
● Increasing the amount of branching reduces the strength of dispersion forces
● The position of the -OH group whether the alcohol is primary secondary or tertiary
affects the boiling point `

Solubility in water
● Dissolving alcohols in water involves breaking the intermolecular bonds between alcohol
molecules and dorming new ones with water molecules
● Substances will dissolve of the new bonds formed are similar in strength to the pre
existing bonds
 ● Alcohols with shorter chains dissolve very easily with water because they are similar to
pre existing bonds making bonds quicker with water
● Alcohols are much less soluble in organic solvents

Reactions of alcohols

Combustion of alcohols
Alcohols burn readily in an excess of oxygen to form carbon dioxide and water

Substitution with Hydrogen Halides

The partially positive charge on the carbon atom makes it susceptible to attack from other
molecules attracted to positive charge
- Alcohol + Hydrogen Chloride -> Haloalkane + Water

Dehydration of Alcohols
Removing one or more molecule of water using aluminium oxide or concentrated acid as
catalyst
- Alcohol -(catalysts) --> H2O + ALKENE

Oxidation of Alcohols

- Oxidising agents a substance that has the ability to oxidise other substance by removing
electrons from them
- Oxidation of alcohols uses either Acidified potassium dichromate or acidified potassium
permanganate

Oxidation of Primary Alcohols ( this part is weak for u)

● Primary alcohols oxidised to form aldehydes
● Two hydrogens have removed
● Carbon and Oxygen can each form one more bond
● A carbon oxygen double bond forms
● 1-propanol — (Acidified Dichromate) —> propanal — ( Acidified Dichromate) (heat)
—--> Carboxylic Acid only for primary alcohol secondary produce ketones
● Further oxidation to form carboxylic acid requires harsh conditions
● Ketones: A compound with carbonyl functional group where the carbon is not bonded to
a hydrogen

Making Alcohols Using Fermentation

Fermentation
- The chemical breakdown of a substance using a living microorganism like bacteria or
yeast
- Glucose → ethanol + carbon dioxide
Fermentation of Glucose
● C6H12O6 (aq) → 2C2H5OH (aq) + 2CO2 (g)
● Glucose - A carbohydrate a type of organic compound containing carbon, hydrogen and
oxygen
● Yeast produces enzymes that convert sugars into ethanol and carbon dioxide
● Temperature of 25C to 40C
● No oxygen
Fractional Distillation
Separating substances based on their boiling points based on their boiling points
● Ethanol is removed from the mixture through distillation
● Mixture is heated
● Concentrated aqueous ethanol is collected
● Distilled again to purify

Fossil Fuels and BioFuels

● A fuel is a substance which stores chemical energy that can be released to use as heat
or power.
● Renewable fuels are derived from materials that can be replenished as they're
used (e.g. plant material)
● Non-renewable fuels are derived from materials that take longer to form than
they're used, so aren't considered replaceable (e.g. fossil fuels)
 ● Fossil fuels are formed from the remains of plants and animals that decay over millions
of years. Examples include:
● Coal, which is formed from decaying wood
● Crude oil, a mixture of hydrocarbons formed from animal remains exposed to
intense heat and pressure
● Natural gas, a mixture of gases formed from animal and plant remains exposed
to intense heat and pressure
● Biofuels are fuels that are derived from plant materials. Examples include:
● Biogas, which is formed during the anaerobic breakdown of organic waste
● Bioethanol produced during the fermentation of starch
● Biodiesel, consisting of esters derived from vegetable oils and animal fats
Comparing Fossil Fuels and Biofuels

Environmental Impact of Fossil Fuels and Biofuels

WRITE THIS PART MORE

Introduction to Aldehydes and Ketones

Aldehydes
● contains carbonyl functional group
● Always end have the o and H
Ketones
● A type of organic compound containing a carbonyl functional group in the middle of the
hydrocarbon in chain
● Has carbonyl group in middle

They both have strong aroma and are responsible for many natural fragrances

Introduction to Carboxylic Acids

- A homologous series of molecules contain the carboxyl functional group

Acid-Base Reactions of Carboxylic Acids

Ionisation of water
 Acid - A substance that donates protons
A weak acid - Acids that only partially ionises when dissolved in water

Acid-Base Reactions
Acid + Base → Salt
Produce three products

Introduction to Amines and Amides

Amines: Close relatives to ammonia

NH2
Primary Amines: Organic molecules containing the amino ( NH2) functional group. Ammonia
with one hydrogen replaced with an alkyl group.
Secondary Amines: Ammonia with two hydrogens replaced with alkyl groups

Amides : Derivatives of carboxylic acids with -OH in the carboxyl group replaced with -NR2.
Basically Carboxylic acid but has NH2 instead of -OH
Naming it would be eg propanamide

Introduction to Esters

Condensation Reactions: Formation of Esters

Esterification: Carboxylic Acid + Alcohol —(Sulfuric Acid) + ( Heat)---> Larger Molecules By product
+ Water (IT IS REVERSIBLE)
- This is a reversible reaction so we need to ensure that the ester and water don't
recombine to from the original carboxylic acid and alcohol by distilling the water
- Natural and synthetic smells and flavours

Identifying and Naming Esters

Ester Functional Group - (COO-)
Naming Ester
- First part is alcohol and second part is carboxylic acid
Structure of Soaps and Detergents:
- Long hydrocarbon chain nonpolar tail and polar head like the phospholipid bilayer
- Anionic Detergents Negatively charged polar head→ Overall negatively charged ion =
Forms a salt
- Cationic Detergents same thing but positively charged polar head → Overall positively
charged ion
- Non- ionic Detergents: The polar head has no charge → complete neutral molecule
Structure of Soaps and Detergents:
- Their structure allows them to form bonds with polar and nonpolar solvents
Non-polar tails: Hydrocarbons tails form dispersion forces with each other
- Dissolves in non-polar solvents : the strength of the forces between the tails and
non-polar solvent is similar to that of the forces between the tails Eg like solvents like oils
- Polar heads: Form dipole dipole forces and hydrogen with each other
Dissolves in polar solvents like water
Example: You have split some olive oil onto your hands and want to wash it off with water. Water
is polar so it can't wash away the oil which is non-polar. Here soap helps, the nonpolar region of
the soap dissolves the non-polar oil on your hands. Simultaneously the polar water washes the
non-polar oil that has picked up by the nonpolar end of the soap molecules
Emulsion: A suspension of two normally insoluble or immiscible liquids with each other

Introduction to Reaction Pathways

What is a reaction pathway?

A series of reactions used to convert a reactant with one functional group to a product with a
different functional group
- Also called synthesis routes as they involve choosing a route to synthesis a compound
Flowchart of Reactions:

Comparing Boiling Point and Solubility of Organic Compounds: (MORE

PRACTICE)
Polar compounds tend to have much higher boiling points and solubility than
non-polar hydrocarbons.
● Hydrocarbons can only form dispersion forces with other
nonpolar molecules.
● Haloalkanes, aldehydes and ketones form dipole-dipole
interactions with other polar molecules.
● Alcohols, carboxylic acids, amines and amides form hydrogen
bonds.
● The boiling points of polar organic compounds can generally be ordered
as:
 ● amides > carboxylic acids > alcohols > ketones and aldehydes > amines
● Non-polar hydrocarbons are insoluble in water, but highly soluble in
organic solvents.
● Small polar molecules are highly soluble in water.
● As the chain length increases, the solubility of polar molecules
decreases in water and increases in organic solvents.
● Branching reduces the ability of a functional group to form hydrogen
bonds, lowering boiling point and solubility in water.

Introduction to Polymers NEED PRACTICE

Monomers: A single unit of a large molecule called a polymer

- Monomers need to have ends containing certain functional groups that will react and
release a water molecule
Polymers: A large molecule made up of many repeating units of a small molecules called
monomers
- Formed when monomers join together through either of two reactions Addition or
Condensation = Different monomers have different properties which determines the type
of polymer formed
Addition Polymers ( NEED TO LEARN NAMING POLYMERS): Formed through a series
of addition reactions combing lots of monomer to form a huge polymer no by products are
formed
- Only unsaturated molecules undergo addition reactions because the double bind can
open up and attach to their atoms
- The monomers needed to form addition polymers need to be unsaturated molecules so
that the double bond can open up
- Multiple alkene molecules are bonded together during the reaction
- Addition Polymerisation: Combining lots of monomers to form one huge polymer with no
byproducts formed
- Does not happen spontaneously
- Conditions: High temperature (makes them more flexi) and high pressure, short chains
of polyethylene form and branch off the main polymer chain
Addition Polymer Properties and Uses:
General Properties: Lots of dispersion forces and solid at RTP have high BP
- Durable materials
- Low densities making them lightweight
- Are non conductors of electricity
Different Structures:
- Crystalline: Polymer chains packed tightly and arranged in orderly parallel fashion eg
HDPE
- Amorphous: Polymer chains are tangles and randomly arranged dispersion forces here
are weaker flexible and transparent
- Vulcanisation: Heating rubber with sulphur to make it more durable by forming
cross-links between polymers
Condensation Polymers: Combining two or more molecules to form a larger molecule and a
small molecule as a byproduct
- To form an ester the functional group of a carboxylic acid and a hydroxyl group react to
form the ester, losing a water molecule in the process
- Condensation polymerisation: Combing many monomers to form a polymer and a small
byproduct
Types of Condensation Polymers : Polyesters, polyamides (eg POLYPEPTIDES)and
polysaccharides

Repeating Units and Monomers: Sometimes two different monomers make a

copolymer + water
- Identify need practice

Condensation Polymers Properties and Uses:

Nylon - 6,6
- structure: strong hydrogen bonds
- Properties: Strong fibres with high tensile strength
As the carbon chain length increases melting point decreases and absorb decreases