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1:
Know that a hydrocarbon is a compound of hydrogen and carbon only
Hydrocarbons
Crude oil: A mixture of hydrocarbons.
Further rules
When there is more than one carbon a functional group can be located it is important to distinguish which carbon the
functional group is on. Each carbon is numbered and these numbers are used to describe where the functional group is
When 2 functional groups are present di- is used as a prefix to the second part of the name
Branching also needs to be considered, the carbon atoms with the branches are described by their number
When the location of functional groups and branches needs to be described the functional group takes precedence so the
functional group has the lowest number
Examples
Specification Point 4.5:
Understand how to write the possible structural and displayed formulae of an organic molecule given its molecular formula
Displayed & Structured Formulae
Displayed formula:
A graphic representation that shows the symbols for each atom in a compound, with straight lines joining them to
represent the covalent bonds.
From the molecular formula, we know that ethene has 2 carbon atoms and 4 hydrogen atoms:
Carbon atoms will be joined by a double bond as each carbon atom needs 4 bonds in total
Structural Formula:
A condensed representation that shows the symbols for each atom in a compound, with straight lines joining them to
represent the covalent bonds.
Example: Ethene
This displayed formula of ethene can be split up into sections and written as a formula:
Combustion: This is the scientific term for burning. In a combustion reaction, a substance reacts with oxygen to form
carbon dioxide (or carbon monoxide if incomplete combustion) and water.
Example: Alkenes burn when heated in air of oxygen
If there is an unlimited supply of air / oxygen, the products are carbon dioxide and water:
CH4 + 2O2 → CO2 + 2H2O
Thick, sticky, black liquid that is found under porous rock (under the ground and under the sea).
Crude oil under the sea
If any fraction from crude oil is burned, then carbon dioxide and water is produced – this shows that crude oil is a complex
mixture of hydrocarbons:
Explanation:
In the fractionating column, it is hot at the bottom and cool at the top.
Crude oil will enter the fractionating column and will be heated so vapours will rise and evaporate.
Vapours of hydrocarbons with very high boiling points will immediately turn into liquid and are tapped off at the bottom of
the column.
Vapours of hydrocarbons with low boiling points will rise up the column and condense at the top to be tapped off.
The different fractions will condense at different heights according to their boiling points and will be tapped off as liquids.
All the fraction are mixtures of different kinds of hydrocarbon.
To conclude the smaller hydrocarbons are collected at the top of the fractionating column as gases. The bigger
hydrocarbons are collected at the lower sections of the fractionating column.
Colour: As carbon chain length increases, liquid colour gets darker, as it becomes thicker and more viscous.
Melting point/boiling point: As the molecules get larger, the intermolecular attraction becomes greater, so more energy in
the form of heat is needed to separate the molecules. With increasing molecular size there is an increase in boiling point.
Volatility: Volatility refers to the tendency of a substance to vaporise. As their molecular size increases, hydrocarbon
liquids become less volatile
Specification Point 4.11:
Know that a fuel is a substance that, when burned, releases heat energy
Fuel
Fuel: Substance which when burned, releases heat energy
This heat can be transferred into electricity, which we use in our daily lives
Examples:
During the complete combustion of hydrocarbons, carbon dioxide and water will be produced:
Incomplete combustion: Occurs when there is a limited supply of air so that elements in the fuel do not fully react with
Oxygen
Incomplete combustion of Hydrocarbons:
During the incomplete combustion of hydrocarbons, water will still be produced but instead of carbon dioxide, carbon
monoxide (soot) will form
Equation:
When carbon monoxide is produced by incomplete combustion, it is absorbed in the lungs and binds with the haemoglobin
in our red blood cells.
This reduces the capacity of the blood to carry oxygen.
Specification Point 4.14:
Know that, in car engines, the temperature reached is high enough to allow Nitrogen and Oxygen from air to react, forming
Oxides of Nitrogen
Formation of Oxides of Nitrogen in Car Engines
Formation of oxides of nitrogen in car engines:
When fuels are burned in car engines, high temperatures are reached which allows Nitrogen and Oxygen from the air to
combine to produce Nitrogen monoxide:
Nitrogen + Oxygen → Nitrogen Monoxide
Both Nitrogen monoxide and Nitrogen dioxide are produced in car engines as a result and is referred to as NOx
During the combustion of Hydrocarbon fuels, impurities such as Sulfur compounds will be oxidised to produce sulfur
dioxide:
Sulfur + Oxygen → Sulfur Dioxide
Sulfur dioxide will react with oxygen and dissolve in water droplets in clouds, forming dilute sulfuric acid which will cause
acid rain:
Sulfur Dioxide + Oxygen + Water → Sulfuric Acid
2SO2 (g) + O2 (g) + 2H2O (l) → 2H2SO4 (aq)
Nitrogen oxides will dissolve in water droplets in clouds, forming dilute Nitric acid and Nitrous acid, causing acid rain:
Nitrogen Dioxide + Water → Nitric Acid + Nitrous Acid
Explanation:
Cracking allows large hydrocarbon molecules to be broken down into smaller, more useful hydrocarbon molecules.
Fractions containing large hydrocarbon molecules are heated at 600 – 700°c to vaporise them.
Vapours will then pass over a hot catalyst of silica or alumina
This process breaks covalent bonds in the molecules, causing thermal decomposition reactions.
As a result, cracking produces smaller alkanes and alkenes. The molecules are broken up in a random way which produce
a mixture of alkanes and alkenes.
Specification Point 4.18:
Explain why cracking is necessary, in terms of the balance between supply and demand for different fractions
Why Cracking is Necessary
Although there is use for each fraction after the fractional distillation of crude oil, the amount of longer chain hydrocarbons
produced is far greater than needed.
However, the amount of shorter chain hydrocarbons produced is far less than needed (e.g. gasoline fraction) and there is a
higher demand for shorter chain hydrocarbons. This is why cracking is necessary to increase the supply of shorter chain
hydrocarbons.
Short chain hydrocarbons burn well and flow well.
Cracking is used to produce petrol for cars.
Cracking also produces alkenes which are raw material in the plastic industry.
Cracking is used to produce hydrogen gas which is a raw material in manufacture of ammonia in Haber process.
Example: The Cracking of hexane (C6H14) to produce butane (C4H10) and ethene
C2H4):
Equation:
Classification of alkanes:
Alkanes are classified as saturated hydrocarbons as all the bonds in alkanes are single bonds
Isomers: compounds that have the same molecular formula but different displayed formulae
This reaction is a substitution reaction because one of the hydrogen atoms from the methane is replaced by a bromine
atom
Alkenes are classified as unsaturated hydrocarbons as they contain a double covalent bond. See examples above.
Specification Point 4.26:
Understand how to draw the structural and displayed formulae for alkenes with up to four Carbon atoms in the molecule,
and name the unbranched-chain isomers
Formulae for Alkenes
Alkenes: A homologous series of hydrocarbon compounds with double Carbon bonds that has the general formula cnH2n
Isomers: Compounds that have the same molecular formula but different displayed formulae
The reaction between bromine and alkenes is an example of a type of reaction called an addition reaction. This reaction is
an addition reaction as the diatomic bromine atom has been added across the double bond of the ethene.
Alkenes: A homologous series of hydrocarbon compounds with double carbon bonds that has the general formula CnH2n
The result of the test using bromine water with alkanes and alkenes
Explanation:
Example:
Specification Point 4.30C (Paper 2C Only):
Understand how to draw structural and displayed formulae for Methanol, Ethanol, Propanol (propan-1-ol only) and Butanol
(butan-1-ol only), and name each compound
Alcohol: Family of organic (carbon-based) compounds that all contain the -OH group that is responsible for their chemical
properties and reactions.
Oxidation of Ethanol
*complete combustion of ethanol:
Ethanol can be oxidised by the process of complete combustion as ethanol burns when heated in air or oxygen:
*microbial oxidation:
So once a bottle of wine has been opened, it can quickly turn into vinegar due to the large number of bacteria in the air.
Ethanol can be oxidised by heating it with an oxidising agent such as Potassium dichromate (vi) in dilute Sulphuric acid.
The alcohol is oxidized to a carboxylic acid.
If the oxidation occurs, then the orange solution containing the dichromate (vi) ions is reduced to a green solution
containing chromium (ii) ions:
Ethanol (C2H5OH) is the type of alcohol found in alcoholic drinks such as wine and beer. It is also used as fuel for cars.
Manufacture of Ethanol
Reacting ethene with steam (hydration):
A mixture of ethene and steam is passed over a hot catalyst of phosphoric acid at a temperature of 300°c and 60-70
atmospheres of pressure and is then condensed into a liquid for use:
Ethene + Water → Ethanol
Equation showing the reaction that takes place between ethene and steam
Fermentation of glucose:
Sugar or starch is dissolved in water and yeast is added to be fermented at 30°C with the absence of oxygen for a few days.
Yeast contains zymase enzymes (biological catalysts) break down starch or sugar to glucose. The yeast respires
anaerobically using the glucose to form to ethanol and carbon dioxide:
Comparing methods
Specification Point 4.33C (Paper 2C Only):
Understand the reasons for fermentation, in the absence of air, and at an optimum temperature
Fermentation: a chemical process in which microorganisms such as yeast act on carbohydrates to produce ethanol and
carbon dioxide. Sugars and starch are examples of carbohydrates.
Conditions of Fermentation
Carboxylic acids contain the carboxyl functional group (-COOH) and will always be at the end of the carbon chain
Carboxylic acids are weak acids, so they can donate a hydrogen ion (H+) in acid-base reactions:
Metals
Carboxylic acids will react with metals to produce a salt and hydrogen gas:
Mg 2CH3COOH Mg(CH3COO)2 H2
Metal Carbonates
Carboxylic acids will react with metal carbonates to produce a salt, water and carbon dioxide:
The microbial oxidation of ethanol will produce a weak solution of vinegar (ethanoic acid).
This occurs when a bottle of wine is opened as bacteria in the air (acetobacter) will use atmospheric oxygen from air to
oxidise the ethanol in the wine.
Ethanol + Oxygen → Ethanoic Acid + Water
Example: Ethanoic acid will react with ethanol in the presence of concentrated sulfuric acid (catalyst) to form ethyl
ethanoate:
The first part of the name indicates the length of carbon chain of the alcohol, and it ends with the letters ‘- YL ‘
The second part of the name indicates the length of carbon chain of the carboxylic acid, and it ends with the letters ‘- OATE
‘.
Properties of Esters
These properties of esters make them useful for food colourings and perfumes:
Volatility: Esters are very volatile as they only have weak attractive forces between their particles so can evaporate easily
(readily change from a liquid to a gas).
Distinctive smell: Esters are chemicals with pleasant ‘fruity’ smells, e.g. pentyl butanoate smells of strawberries.
A mixture of ethanoic acid, ethanol and concentrated sulfuric acid is gently heated by either a water bath or an electric
heater (ethanol is flammable, so a Bunsen can’t be used!)
The ester is then distilled off as soon as it is formed and collected in a separate beaker by condensation.
As esters have low boiling points (they are volatile), they are the first to evaporate from the reaction mixture. Removing
them from the mixture by distillation prevents the reverse reaction from occurring.
Result:
The distillate can be smelt to check whether an ester has been produced.
Small quantities of ethanoic acid, sulfuric acid and ethanol can also be collected in the process.
To remove acidic impurities, sodium carbonate solution can be added, until the mixture stops fizzing (no more carbon
dioxide is evolved).
To remove ethanol, calcium chloride solution can be added.
Specification Point 4.44:
Know that an addition polymer is formed by joining up many small molecules called monomers
Monomer: The unit molecule from which a polymer is made
Addition Polymers
Formation of addition polymers:
Addition polymers are formed by the joining up of many small molecules called monomers.
Alkenes can act as monomers as they are unsaturated so the double bond can break and bond with other monomers.
Natural Polymers.
e.g.: starch, carbohydrate, fat, protein etc.
Synthetic polymers (Man-made polymers).
e.g.: polythene, polypropene, polychloroethene (PVC), polystyrene, nylon, terylene.
Specification Point 4.45:
Understand how to draw the repeat unit of an addition polymer, including Poly(ethene), Poly(propene), Poly(chloroethene)
and Poly(tetrafluoroethene)
Drawing Repeating Units
Polymer molecules are very large compared with most other molecules, so repeat units are used when displaying the
formula:
Change the double bond in the monomer to a single bond in the repeat unit.
Add a bond to each end of the repeat unit.
Landfills:
Waste polymers are disposed of in landfill sites but this takes up valuable land as addition polymers are non-biodegradable
so micro-organisms such as decomposers cannot break them down.
This causes sites to quickly fill up
Incineration:
Polymers release a lot of heat energy when they burn and produces carbon dioxide which is a greenhouse gas that
contributes to climate change.
If incinerated by incomplete combustion, carbon monoxide will be produced which is a toxic gas that reduces the capacity
of the blood to carry oxygen.
Recycling:
Polymers can be recycled but different polymers must be separated from each other.
This process is difficult and expensive.
Condensation polymerisation: A reaction in which two different types of monomer join together to produce a polymer and
expel a small molecule such as water.
Example:
The condensation polymerisation between terephthalic acid and ethane -1,2 diol
The basic structure of a polyester, the box represents any group of atoms
Equation:
Biopolyesters are a specific type of polymer that is able to biodegrade naturally in the environment after their intended
purpose.
The polymers are synthetically made, consisting of ester, amide and ether functional groups which gives them the
characteristic of being biodegradable.