TOPIC 11 ORGANIC CHEMISTRY - Part 1

11.3 Fuels
Refining Petroleum (Crude Oil)

Fossil fuels ……………., ……………………….., and …………. ….. (mainly methane)

are made up of molecules with carbon chains of different lengths.

They burn in very exothermic reactions which is what makes them excellent fuels.

Fossil fuels are hydrocarbons

Definition: A hydrocarbon …………………………………………………………………
…………………………………………………………………………………………………………..

Petroleum (crude oil ) is a mixture of hundreds of hydrocarbons (a big thick, smelly liquid of
no use to anyone). Petroleum is made up of hydrocarbons called ……………….. .

Examples
Methane
Molecular Formula …………… Structural Formula :…….

Displayed Formula

Dot and Cross

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Ethane 2C
Molecular Formula …………… Structural Formula :……………..

Displayed Formula

Dot and Cross

Propane 3C
Molecular Formula …………… Structural Formula :……………..

Displayed Formula

Butane 4C
Molecular Formula …………… Structural Formula :……………..

Displayed Formula

The alkanes are then named depending on the number of carbons in the chain

5C ………….. 8C…………
6C ………….. 9C………..
7C ………….. 10C………..

At the refinery, these are sorted into groups of useful substances called fractions. Refining
is the separation into groups of molecules of similar size.

The process is fractional distillation and uses the different boiling points to separate the
molecules of similar size (length of C chains)

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Fractional Distillation
 The petroleum mixture is heated until it vaporises.
 It then passes up a tall tower that is hot at the bottom but cool at the top.
 As the vapour passes up this tower the molecules cool and condense back to liquid
depending on their boiling point

gas used in heating and cooking

fuel used in cars

used as a chemical feedstock

used for jet fuel

fuel used in diésel engines

fuel used in ships and

home heating systems

lubricants, waxes and

polishes

for road making and

roofing

You do not need to memorise the temperatures but you do need to know the
fraction name and the uses!

The properties of the fractions change as you go up the column

(a) ………………………………………
(b) …………..…..........................
(c) ……………………………………….
(d) ……………………………………….

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Complete Q1-3 p225 and p227
Complete worksheet 18.4 Fuels and 18.5 Petroleum Fractionation
Complete Q2 Practise Questions 2 and 6

Cracking of Alkanes
• Oil companies find that they have too many large hydrocarbons after refining/distillin
oil.
• Yet the smaller hydrocarbons like petrol are in great demand than the supply.
• Scientists have found a way to change the larger, less useful, long chain alkanes into
smaller short chain more useful ones.
• At least one product is a small alkene which can be used to make plastics other
chemicals
• Cracking is an example of thermal decomposition

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Cracking in the Lab

Ethene gas collected

Cracking is carried out using ………. …………………. and a ……………….

Test for an alkene - unsaturation C=C e.g. ethene gas :
Turns orange bromine water colourless

Watch the video of cracking and suckback

To prevent suckback, …………….,. …………………………………………….

e.g. Decane
Equation

e.g. Octane
Equation

When small alkanes are cracked, hydrogen can be produced

e.g. Ethane
Equation

Cracking always produces short chain compounds with C=C carbon – carbon double
bonds - alkenes . This bond makes them more reactive so they can be used to make
plastics and other substances
What do you call 2 mad scientists in an oil refinery?
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CRACKERS!

Complete Q1-3 p233

Complete worksheet 19.2 Cracking alkanes

Homologous Series

These are:
• families of similar organic molecules with the same functional group
• molecules with the same general formula
• compounds with similar chemical properties
• compounds with a trend of gradually changing physical properties, eg. melting points slowly
increase as a chain gets longer (adding CH2)

We are going to look at the following homologous series:

I. Alkanes
II. Alkenes
III. Alcohols
IV. Carboxylic acids

I. The Alkanes
Hydrocarbons joined together by single covalent bonds.

General formula: ………………………………

Alkanes are S……………….. molecules as they have only S……….. C-C bonds.

Complete the worksheet on alkanes overleaf

Research: Find the boiling point for the first 10 alkanes, and add them to the table.
Label them as solids (S), liquids (L) or gases (G) at room temperature.

The longer the chains, the stronger the intermolecular forces, so the higher the
melting and boiling points.
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Reactions of Alkanes

The bonds in the alkanes are strong and hard to break, making them unreactive.

There are 2 types of reaction than you must know...

1. Combustion

With plenty of oxygen, the products are carbon dioxide and water...
Eg. Pentane

With limited oxygen, carbon monoxide and even carbon can be produced...

Combustion is very exothermic, and explains why these compounds are used as fuels, eg. natural
gas (mainly methane) in the home, and butane/propane as camping gases, octane and diesel in
vehicles.

2. Substitution reactions with chlorine (and other halogens)

Alkanes react with halogens and their hydrogen atoms are slowly replaced. These are
photochemical reactions. The classic and explosive example is...
Methane and chlorine (in UV light) where the ultraviolet light provides the activation energy, Ea
EQNs: displayed and molecular

Complete Q1-3 p231

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EQN Propane and chlorine

What happens if there is no u.v. light – in the dark?

Complete Q1-3 p231

Isomers of alkanes

Definition of Isomer :
………………………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………….
.

e.g. pentane

e.g. propane

Complete the worksheet 19.1 Alkanes

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II. Alkenes

These are more reactive hydrocarbons, as they contain a Carbon-Carbon double bond. They
are made by cracking (see earlier).

General Formula: …………………………………..

Alkenes are u……………………… molecules as they have a C=C doublé bond where as alkanes are
S ……………….......molecules

Draw the displayed structure of three of them

Draw the dot and cross of ethene to show the C=C bond

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Draw structural isomers of butene (move the position of the C=C)

Draw structural isomers of pentene

Reactions of Alkenes
Alkenes are much more reactive than alkanes due to their C=C bond.

As hydrocarbons they of course do combustión

1. Combustion.
e.g. with ethene

2. Addition Reactions of Alkenes (in contrast to substitution reactions of alkanes)

Atoms are added across the carbón carbón dounble bond C=C.

There are 4 ADDITION reactions you need to know. They produce ONE PRODUCT only.

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Four Addition Reactions of Alkenes
1. With Bromine water / Test for unsaturation (C=C)
If the alkenes come into contact with bromine water, decolourisation results...
Eg. Ethene with bromine water

EQN:

Molecular formula

Displayed formula

Indicate the colour of reactants and products.

The bromine is “added” to the double bond.

NB Alkanes will not react with Bromine water as they do not have a C=C (no decolourisation)

EQN

2. With hydrogen (HYDROGENATION)

The hydrogen adds to the double bond, in the presence of a nickel
catalyst at high temperature producing the alkane.

Eg. Propene with hydrogen

EQN:

This reaction is used to convert unsaturated vegetable oils into margarine.

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3. With steam (and phosphoric acid – acid catalyst)
Here, an alcohol is produced...
Eg. But-1-ene

EQN:
Molecular formula

Displayed formula

Complete Q1-3 p235

Complete Worksheet 19.3

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. Eg. Propene at high temperature and pressure

EQN:

With 3 units
Common Mistake

With n units

Name the polymer

Uses:……………………………………………………………………………………………………………….

Identify the monomer from the polymer

Identify the repeating unit ignore the brackets and add a double bond

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