Year 11 Chemistry

Topic 10
6 LESSONS
Organic Chemistry:
Alkanes

Name: ___________________________
Form: ___________
Teacher:________________________

Teacher Comments:

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Topic 10: Organic Chemistry: Alkanes
Spec Detail Studied Revised Confident
Point

Lessons 1 and 2
4.19 Know the general formula for alkanes.
4.20 Explain why alkanes are classified as saturated hydrocarbons.
4.21 Understand how to draw the structural and displayed formulae for alkanes with
up to five carbon atoms in the molecule, and to name the unbranched-chain
isomers.
4.2 Understand [using alkanes as examples] how to represent organic molecules
using empirical formulae, molecular formulae, general formulae, structural
formulae and displayed formulae.
4.3 Know [using alkanes as examples] what is meant by the terms homologous
series, functional group* and isomerism.

*(Alkanes are notable for their lack of functional group, however this term will
become important in the next topic [alkenes]). These topics are covered throughout the
4.4 Understand [using alkanes as examples] how to name compounds relevant to whole of organic chemistry
this specification using the rules of International Union of Pure and Applied
Chemistry (IUPAC) nomenclature.

Students will be expected to name compounds containing up to six carbon

atoms.
4.5 Understand [using alkanes as examples] how to write the possible structural
and displayed formulae of an organic molecule given its molecular formula.
Lessons 3 and 4
4.11 Know that a fuel is a substance that, when burned, releases heat energy.
4.12 Know the possible products of complete and incomplete combustion of
hydrocarbons with oxygen in the air.
4.13 Understand why carbon monoxide is poisonous, in terms of its effect on the
capacity of blood to transport oxygen.
References to haemoglobin are NOT required.
4.14 Know that, in car engines, the temperature reached is high enough to allow
nitrogen and oxygen from the air to react, forming oxides of nitrogen.
4.15 Explain how the combustion of some impurities in hydrocarbon fuels results in
the formation of sulfur dioxide.
4.16 Understand how sulfur dioxide and oxides of nitrogen contribute to acid rain.
Lessons 5 and 6
4.22 Describe the reactions of alkanes with halogens in the presence of ultraviolet
radiation, limited to mono-substitution.

Knowledge of reaction mechanisms is NOT required.

4.17 Describe how long-chain alkanes are converted to alkenes and shorter-chain
alkanes by catalytic cracking (using silica or alumina as the catalyst, and a
temperature in the range 600 – 700 C).
4.18 Explain why cracking is necessary, in terms of the balance between supply and
demand for different fractions.

TASKS: Within each lesson you’re expected to work through the notes, reading each page carefully, filling in
blanks and answering any questions as you go. Use the teacher videos on Teams, and your textbook page
255 to 281 to help you.

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LESSON 1
You’ve just studied how crude oil is separated into different fractions. Fractions are mixtures of lots of different
types of molecules. We are now going to zoom into each fraction further and look at the types of molecules we find
there. We can group molecules that share certain characteristics into families called homologous series.

For example, let’s zoom into the refinery gas fraction and see what’s in there….

Let’s now zoom into the second fraction, gasoline. You’ll see that we have more members of the alkane and alkene
homologous series in there: larger molecules than in the first fraction (which make sense, as the boiling points are
larger for this second fraction).

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Instead of studying each fraction in turn, it makes more sense to study each homologous series in turn. That’s because
within each homologous series, the chemistry of the members is very similar. We’ll start with the alkanes (… that’s
this topic) and move on to the alkenes (… that’s the next topic).

The next few pages of notes will throw a lot of definitions at you, which may seem a bit daunting at first, and some
will not make a lot of sense for now. My advice is to read through it once now, and then, as you meet each homologous
series in turn, come back to these initial pages and read back through them.

Homologous Series
Definitions (LEARN):

Homologous series: Members of the same homologous series:

1. have the same general formula

2. have similar chemical properties (because they have the same functional group)
3. differ by CH2 in molecular formulae from neighbouring compounds
4. show a gradual variation in physical properties (for example boiling points increase as you
increase the number of CH2)

Functional group: This is part of the molecule which usually determines the molecule’s reactivity. Members of the
same homologous series have the same functional group.

Examples of some homologous series are alkanes, alkenes, alcohols and carboxylic acids:
Homologous series: Alkanes Alkenes Alcohols Carboxylic acids

Functional group none C=C O-H COOH

First 6 members: methane methanol methanoic acid

ethane ethene ethanol ethanoic acid
propane propene propanol propanoic acid
butane butene butanol butanoic acid
pentane pentene pentanol pentanoic acid
hexane hexene hexanol hexanoic acid

Note the prefixes:

Meth, eth, prop, but, pent, hex, hept, oct, non, dec
1C, 2C, 3C, 4C, 5C, 6C, 7C, 8C, 9C, 10C

Hydrocarbon: Hydrocarbons are molecules that consist of hydrogen and carbon only.
Examples of hydrocarbons are any alkane or alkene.

Drawing display formulae

THE GOLDEN RULES: CARBON HAS 4 BONDS! Tips: Draw the carbon chain out first, making
sure you’ve got the right number of carbons Fill
HYDROGEN HAS 1 BOND! in the rest of the bonds with hydrogens, making
sure you’re obeying the GOLDEN RULES.
OXYGEN HAS 2 BONDS!

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Alkanes
General formula: CnH2n+2

Functional group: none

Alkanes are saturated.

Definition of saturated: _________________________________________________

Alkanes are hydrocarbons

Definition of hydrocarbon: _______________________________________________

What is the major source of hydrocarbons (i.e. where do we get most of our hydrocarbons from?)

__________________________________________________________________________

Names of the first six members of the alkane homologous series

Displayed formula Condensed structural Molecular formula Empirical formula

(shows all covalent bonds) formula (shows each C (adds up all of each (shows simplest
Name
in turn and what’s type of atom ratio of atoms in
attached to it) together) the molecule)

Methane

Ethane

Propane

Butane

Pentane

Hexane

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Bonding and Structure Reminder!

Alkanes all have ________________ bonding and have a ______________________________ structure.

Draw dot and cross diagrams for:

Methane

Propane

Questions

1. Why do alkanes have relatively low boiling points?

……………………………………………………………………………………………………………………………………………………………………………………

……………………………………………………………………………………………………………………………………………………………………………………

……………………………………………………………………………………………………………………………………………………………………………………

2. Why does butane have a higher boiling point than methane?

……………………………………………………………………………………………………………………………………………………………………………………

……………………………………………………………………………………………………………………………………………………………………………………

……………………………………………………………………………………………………………………………………………………………………………………

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LESSON 2
Drawing (And Naming) More Complicated Molecules

Alkanes can also have branched chains. For example:

• In order to name this, we circle the longest carbon chain. This becomes the end of the name.

• Then we decide what the side chain is. The two you need to know are methyl

and ethyl

• We decide on what number carbon the side chain is on. (note we want the lowest possible number in the
name).

• We are ready to name the alkane. Note we use a hyphen between a number and a word in the name.

Exercise 1: Try naming these

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Exercise 2: Try drawing the display formulae of these

3-methylpentane 1-fluorobutane

3-ethylhexane 2,3-dibromobutane

2,2-dimethylpropane

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Isomers

Isomers are molecules with the same molecular formula but different structural formula

Here are two examples of isomers.

Example 1 Example 2

Example 1. Draw all the isomers of pentane.

Careful you don’t actually draw two molecules that are exactly the same!

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Example 2. Draw all the isomers of hexane.

Many alkanes are used as fuels, so it is important to learn how we can combust them.

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LESSON 3

Combustion Reactions of Alkanes

Combusting means_________________________________________________________.

Complete combustion

Alkanes (and any other hydrocarbon) will burn in plentiful oxygen to give carbon dioxide and water. This is called
complete combustion.

Example: ___________________________________________________

Incomplete combustion

If there is not enough oxygen, full oxidation does NOT occur and carbon monoxide and water can form. This is
known as incomplete combustion.

Example: ___________________________________________________

Writing and balancing equations

Complete the following table.

Note it’s easiest to balance C first, then H and then O in combustion equations.

Name Molecular Equation for combustion

Formula

Complete combustion:
Methane CH4
CH4 + 2O2 → CO2 + 2H2O

Incomplete combustion:
Ethane C2H6

Complete combustion:
Propane

Incomplete combustion:
Butane

Complete combustion:
Pentane

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Combustion Practice Question

The diagram below shows a setup that can be used to test for the products of combustion. Study the
diagram carefully and answer the questions using your own reasoning.

The tea light is made of a waxy hydrocarbon.

(a) Explain the role of the cobalt chloride paper.

………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………

(b) Explain the role of the limewater.

………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………

(c) Suggest the role of the pump.

………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………

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LESSON 4

Problems with Combustion

You need to know these 3 issues. Spend a good 15 minutes learning this table, then cover it up and try and write out
each issue (in bullet points) including the equations.

Gas How it’s formed What problems does this cause?

Carbon monoxide (CO) If combustion happens in limited CO is poisonous because reduces the
oxygen, carbon monoxide (and ability of the blood to carry oxygen. (CO
carbon) can form (in addition to CO2 binds irreversibly to haemoglobin,
and H2O) preventing it bind to O2)

e.g. 2CH4 + 3O2 → 2CO + 4H2O

Sulfur dioxide (SO2) Sulfur-containing impurities can exist SO2 is released into the atmosphere. It
in some hydrocarbon fuels. If these reacts with O2 and H2O in the atmosphere
are combusted, SO2 can form. to form sulfuric acid:

S + O2 → SO2 S + O2 + H2O → H2SO4

This is a major component of acid rain.

Nitrous oxides (NOx)… The high temperature in car engines NOx is released into the atmosphere. It
Nitrogen monoxide (NO) provides enough energy for the reacts with O2 and H2O in the atmosphere
and nitrogen dioxide (NO2) (usually unreactive) N2 and O2 to to form nitric acid.
react.
2NO2 + H2O + ½O2 → 2HNO3
N2 + O2 → 2NO
This is another component of acid rain.

Effects of Acid Rain

• Acidifying lakes, killing fish, killing trees

• Attacks buildings, especially those made of limestone: (H2SO4 + CaCO3 → CaSO4 + H2O + CO2)

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To finish off lesson 4, here are some more complicated questions with naming alkanes. If you can get these
ones right then you can call yourself a master of alkane naming!

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LESSON 5

Reaction of Alkanes with Halogens (in the presence of UV light)

Reaction with chlorine

Conditions Needs UV light

Type of Substitution reaction
reaction (One atom swaps with another: in this case an H atom swaps with a Cl).
Example of
equation
using
display
formulae

How many One

bromines We describe the product as a monochlorolkane, or we can also say just a mono-
appear in substituted chloroalkane.
the main
product?

Reaction with bromine

Conditions Needs UV light

Type of Substitution reaction
reaction (One atom swaps with another: in this case an H atom swaps with a Br).
Example of
equation
using
display
formulae

How many One

bromines We describe the product as a monobromoalkane, or we can also say just a mono-
appear in substituted bromoalkane.
the main
product?
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Note that it doesn’t have to be chlorine or bromine + UV light. Other halogens + UV light will react in the
same way with alkanes. So for example you could have:

Important (when you come to revise it for your exams)

Now go and look at your Alkenes notes to see what happens when alkenes react with
halogens: hint it’s very different!

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LESSON 6

Cracking
Cracking is converting (usually by means of heating) longer hydrocarbons into shorter, MORE USEFUL hydrocarbons
which are MORE IN DEMAND.

These hydrocarbons are generally more useful because:

• They burn more efficiently (i.e. they are better fuels)
• The alkene products are used to make other materials (e.g. polymers)

Note that cracking is a separate process that happens after fractional distillation… (Don’t get the two processes
confused!)

How to crack something:

The hydrocarbons are heated at a temperature of 600 – 700 oC with a silica or alumina catalyst.

Example:

For example, decane (an alkane with 10 carbons) can be cracked to produce octane and ethene.

decane octane + ethene. Octane is used as petrol. Ethene is used in

the manufacture of polymers.

Cracking an alkane produces a smaller alkane plus an alkene. If you add up the number of hydrogen atoms in the
above reaction, you will see that there are 22 on each side. An alkene is produced because the original alkane does
not have enough hydrogen atoms to produce two more alkanes.

Practice Cracking Questions

Write word and balanced symbol equations equations for cracking the following long chain alkanes:

Cracking C14H30 to form propene (C3H6) and one other product

Cracking C13H28 to form ethene (C2H4) and one other product

Cracking C12H26 to form octane (C8H18) and one other product

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Exam-Style Questions
In addition to these questions, don’t forget to look at old preps, old exercises, and MyDulwich. Doing
questions is THE best way to revise, rather than burying your head in a textbook or revision book.

Q1.

(a) Petrol is obtained by the fractional distillation of crude

oil. One substance present in petrol is octane, C8H18. The
structure of a molecule of octane is shown.

(i) Octane is a saturated hydrocarbon.

Explain what is meant by saturated hydrocarbon.

(3)
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................

(ii) Octane is mixed with bromine water and shaken.

Complete the sentence by putting a cross ( ) in the box to show your answer.
On shaking, the colour of the mixture
(1)
A remains orange
B remains colourless
C changes from clear to orange
D changes from orange to colourless

(b) In the oil industry some fuel oil fraction is converted into petrol.

This is done by heating the fuel oil fraction to thermally decompose it and produce smaller
molecules.

(i) State the name given to this process.

(1)
.............................................................................................................................................
Give two reasons why it is necessary to carry out this process to make more petrol.
(2)
reason 1...............................................................................................................................
.............................................................................................................................................
reason 2...............................................................................................................................
.............................................................................................................................................

(c) Methane can be burned in excess oxygen to form carbon dioxide and water.
(3)
.............................................................................................................................................

(Total for question = 10 marks)

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Q2.

In the laboratory this apparatus is used to crack long chain hydrocarbon molecules to form shorter
chain hydrocarbon molecules.

(a) Suggest the role of the broken pot.

(1)
..............................................................................................................................................

(b) When the experiment is complete there is a danger that water will rise up the delivery tube into
the hot test tube.

State what you would do to prevent this.

(1)
..............................................................................................................................................

(Total for Question = 2 marks)

Now self-assess your answers using the mark scheme on the next page.

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Mark Scheme

Q1.

Q2.

Answer Acceptable Mark

answers
(a) catalyst (1)
(b) remove delivery tube (1)
from water before
stopping heating

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IGCSE Chemistry Organic Definitions Glossary
Fractional Distillation - Separating liquids of different boiling points by evaporation and condensing

Combustion - A reaction where a substance burns in oxygen combining to form the oxide and giving out
energy.

Crude Oil - A mixture of hydrocarbons formed from the remains of dead sea life which was covered with
silt on the sea bed and compressed over millions of years

Fossil Fuel - A substance formed from the dead remains of plants or animals which will burn in air e.g. Coal,
natural gas

Hydrocarbon - A substance which contains carbon and hydrogen atoms only.

Cracking - Process where long chain hydrocarbons of little value are broken down by heat and a catalyst
into smaller, more useful hydrocarbons

Saturated - A hydrocarbon which only has single covalent bonds between all atoms.

Unsaturated - A hydrocarbon which has at least one double bond between two neighbouring carbon
atoms.

Alkane - A saturated hydrocarbon with the general formula CnH2n+2 e.g. CH4 – methane

Alkene - An unsaturated hydrocarbon with the general formula CnH2n e.g. C2H4 – ethene

Addition Polymerization - A reaction where many small alkene molecules (monomers) join up to form a
long chain molecule of repeating units (polymer).

Condensation Polymerization - A reaction where different monomers join up to form a long chain
molecule of repeating units (polymer) whilst also producing smaller molecules.

Homologous Series - a group of molecules with the same general formula, the same functional group, very
similar chemical properties (reactions), and a gradation of physical properties (e.g. increasing boiling point
with increasing carbon chain length)

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