Edexcel International A Level Chemistry
Topic 4: Introductory Organic Chemistry and Alkanes
The language of organic chemistry (hazards, families, formulae, names, reaction types, bond breaking) and the first family, the alkanes. Their isomers, their use as fuels, their combustion and the free radical substitution mechanism.
The one idea
Organic chemistry is the chemistry of carbon compounds, and it is organised by families. Every family has a functional group, the part that reacts, and a carbon chain, which mostly sets the physical properties. The alkanes are the family with no functional group: only C–C and C–H single bonds. This makes them a good first family to study. They burn, and they react with halogens in UV light.
Before the chemistry of any family, you need a shared language. A name tells you the structure. A formula can show it in four ways. A reaction type says what kind of change happens. A fission says how a bond breaks, and the particles that result decide the mechanism. This topic builds that language first, then uses it on the alkanes.
Where to find things
| Question | Pages |
|---|---|
| How do I work safely with organic compounds? | 1 |
| What is a homologous series and a functional group? | 2 |
| How do I write and draw a formula? How do I name a compound? | 3 and 4 |
| What types of reaction are there, and how do bonds break? | 5 and 6 |
| What are alkanes and cycloalkanes? | 7 |
| What are structural isomers, and how do I find them all? | 8 and 9 |
| Where do alkane fuels come from? | 10 and 11 |
| What happens when alkanes burn, and what are the problems? | 12 and 13 |
| Why look for other fuels, and what is carbon neutral? | 14 |
| How do alkanes react with halogens? | 15, 16 and 17 |
How to use these notes
- Read the pages in order the first time. Names and formulae (pages 3 and 4) are used on every later page, and the mechanism (page 16) uses the bond-breaking language of page 6.
- Each page opens with its one idea in a sentence. If you can explain it to someone else, you know the page.
- Coloured boxes mean the same thing on every page: definitions you may be asked to quote, key ideas, common mistakes, exam technique, and beyond the spec (interesting, but you will not be examined on it).
- Each page ends with questions and fully worked answers. Cover the answers, try the questions, then mark yourself.
- Use the topic on a page the night before an exam.
This topic has no core practical. Safe working (page 1) is a concept, not a practical. Page 15 describes a simple test tube demonstration of bromine and hexane in light and dark, because the observation is a common exam question. It is not a listed practical.
The skills that earn most marks here are definitions quoted accurately (hazard, risk, homologous series, functional group, structural isomers, free radical, electrophile, carbon neutral), naming and drawing structures correctly, balanced equations (combustion, cracking, radicals with a dot) and explanations that give the reason as well as the fact.
Boiling temperatures are quoted to the nearest degree and carbon ranges for the crude oil fractions are typical values. Books and data booklets differ slightly, so learn the trends, not the last digit.
Pages
- Hazard and risk
A hazard is what a substance could do to you. Risk is how likely it is to happen. Safe working means finding the hazards, judging the risk and cutting it down before you start.
- Homologous series and functional groups
Organic compounds come in families. The functional group sets what a family does in a reaction, and the length of the carbon chain sets the gradual trend in physical properties.
- Ways of writing a formula
Molecular, structural, displayed and skeletal formulae show different amounts of detail. You must be able to write one from another and know what each one shows.
- Naming organic compounds
IUPAC names are built from a stem for the longest carbon chain, plus the names and positions of whatever is attached to it. The same rules let you draw a molecule from its name.
- Types of organic reaction
Most organic reactions fall into five types. You classify a reaction by looking at what happens to the reactants, and a single reaction can belong to more than one type.
- Bond breaking, free radicals and electrophiles
A covalent bond is a shared pair of electrons. It can break evenly, one electron to each atom, to make free radicals, or unevenly, both electrons to one atom, to make ions.
- Alkanes and cycloalkanes
Alkanes and cycloalkanes are hydrocarbons with only single bonds. Their general formulae let you check any formula and tell a chain from a ring.
- Structural isomerism
Structural isomers have the same molecular formula but different structural formulae. There are three ways the atoms can be arranged differently, and naming a drawing is the way to check that two drawings are really different molecules.
- Isomers of alkanes and cycloalkanes
A method for finding every structural isomer of an alkane or cycloalkane up to six carbons, by starting with the longest chain and shortening it one carbon at a time. The answers to learn are 2 for C₄H₁₀, 3 for C₅H₁₂ and 5 for C₆H₁₄.
- Crude oil and fractional distillation
Crude oil is a mixture of hydrocarbons, mostly alkanes. Fractional distillation separates it into fractions by boiling temperature, and the fractions are the fuels we burn.
- Cracking and reforming
Cracking breaks long alkane chains into shorter alkanes and alkenes. Reforming rearranges straight chains into branched and cyclic molecules. Both change the molecules, so both need balanced equations.
- Combustion of alkanes
Alkanes burn in plenty of oxygen to give carbon dioxide and water. With limited oxygen they give carbon monoxide or carbon as well. You must balance both kinds of equation, and use them in calculations.
- Pollutants from burning fuels
Burning alkane fuels releases carbon monoxide, carbon particulates, unburned hydrocarbons, oxides of nitrogen and sulfur dioxide. Carbon monoxide is toxic because it binds to haemoglobin, and the oxides of nitrogen and sulfur make acid rain.
- Alternative fuels and carbon neutrality
Alkane fuels are finite and release pollutants and carbon dioxide. An alternative fuel is judged by whether it is renewable and by its overall carbon dioxide emissions, counting how it is made as well as how it burns.
- Alkanes and halogens
In ultraviolet light, an alkane and a halogen react by substitution. A hydrogen atom is replaced by a halogen atom, and a hydrogen halide is made. Without light there is no reaction.
- Free radical substitution: the mechanism
The reaction of an alkane with a halogen is a chain reaction in three stages. Initiation makes radicals, propagation regenerates them as the product forms, and termination removes them.
- Further substitution and its limits
A chlorine radical can attack the product as well as the alkane, so the reaction goes on to make a mixture. A mixture means a low yield of any one product, which is why free radical substitution is of limited use in synthesis.
Also in this topic: Topic 4 on a page
Spec checklist
Every point you can be examined on in this topic, and where it is explained. Tick them off as you go.
| Spec | You should be able to | Where |
|---|---|---|
| 4.1 | understand the difference between hazard and risk | Hazard and risk are different things |
| 4.2 | understand the hazards associated with organic compounds and why it is necessary to carry out risk assessments when dealing with potentially hazardous materials | Hazards of organic compounds |
| 4.3 | be able to suggest ways in which risks can be reduced and reactions carried out safely, for example: (i) working on a smaller scale (ii) taking precautions specific to the hazard (iii) using an alternative method that involves less hazardous substances | Reducing the risk |
| 4.3(i) | (i) working on a smaller scale | Reducing the risk Work on a smaller scale |
| 4.3(ii) | (ii) taking precautions specific to the hazard | Reducing the risk Take precautions specific to the hazard |
| 4.3(iii) | (iii) using an alternative method that involves less hazardous substances | Reducing the risk Use a less hazardous method |
| 4.4 | understand the concepts of homologous series and functional group | Homologous series Functional groups |
| 4.5 | be able to apply the rules of International Union of Pure and Applied Chemistry (IUPAC) nomenclature to: (i) name compounds relevant to this specification (ii) draw these compounds, as they are encountered in the specification, using structural, displayed and skeletal formulae. Students will be expected to know prefixes for compounds up to C₁₀ | Four formulae for one molecule Stems and prefixes up to ten carbons |
| 4.5(i) | (i) name compounds relevant to this specification | Stems and prefixes up to ten carbons The five naming rules |
| 4.5(ii) | (ii) draw these compounds, as they are encountered in the specification, using structural, displayed and skeletal formulae. Students will be expected to know prefixes for compounds up to C₁₀ | Four formulae for one molecule Structural formulae Displayed formulae Skeletal formulae Drawing a compound from its name |
| 4.6 | be able to classify reactions as addition, substitution, oxidation, reduction or polymerisation | Five types of reaction |
| 4.7 | understand that bond breaking can be: (i) homolytic, to produce free radicals (ii) heterolytic, to produce ions | Two ways to break a covalent bond |
| 4.7(i) | (i) homolytic, to produce free radicals | Homolytic fission |
| 4.7(ii) | (ii) heterolytic, to produce ions | Heterolytic fission |
| 4.8 | know definitions of the terms 'free radical' and 'electrophile' | Free radicals and electrophiles |
| 4.9 | know the general formula of alkanes and cycloalkanes, and understand that they are hydrocarbons (compounds of carbon and hydrogen only) which are saturated (contain single bonds only) | Hydrocarbons and saturation General formulae |
| 4.10 | understand the term 'structural isomerism' and be able to draw the structural isomers of organic molecules, given their molecular formula | Same atoms, different structures Three kinds of structural isomerism |
| 4.11 | be able to draw and name the structural isomers of alkanes and cycloalkanes with up to six carbon atoms | Isomers of alkanes Isomers of cycloalkanes |
| 4.12 | know that alkanes are used as fuels and obtained from the fractional distillation, cracking and reforming of crude oil, and be able to write equations for these reactions | Alkanes as fuels Fractional distillation Cracking Reforming Three processes compared |
| 4.13 | know that pollutants, including carbon monoxide, oxides of nitrogen and sulfur, carbon particulates and unburned hydrocarbons, are emitted during the combustion of alkane fuels | The pollutants and where they come from |
| 4.14 | understand the problems arising from pollutants from the combustion of alkane fuels, limited to the toxicity of carbon monoxide and why it is toxic, and the acidity of oxides of nitrogen and sulfur | Carbon monoxide: why it is toxic Acid rain from oxides of nitrogen and sulfur |
| 4.15 | be able to discuss the reasons for developing alternative fuels in terms of sustainability and reducing emissions, including the emission of CO₂ and its relationship to climate change | Why develop alternative fuels? |
| 4.16 | be able to apply the concept of carbon neutrality to different fuels, such as petrol, bioethanol and hydrogen | Carbon neutrality |
| 4.17 | understand the reactions of alkanes with: (i) oxygen in the air (combustion) (ii) halogens | Complete combustion Incomplete combustion Using the equations Substitution by a halogen |
| 4.17(i) | (i) oxygen in the air (combustion) | Complete combustion Incomplete combustion |
| 4.17(ii) | (ii) halogens | Substitution by a halogen |
| 4.18 | understand the mechanism of the free radical substitution reaction between an alkane and a halogen: (i) using free radicals, which are species with an unpaired electron, represented by a single dot (ii) showing the initiation step of the mechanism, with curly half-arrows for free radical formation (iii) showing the propagation and termination steps of the mechanism (iv) having limited use in synthesis because of further substitution reactions | Radicals and the three stages Initiation Propagation Termination The reaction does not stop at one substitution |
| 4.18(i) | (i) using free radicals, which are species with an unpaired electron, represented by a single dot | Radicals and the three stages |
| 4.18(ii) | (ii) showing the initiation step of the mechanism, with curly half-arrows for free radical formation | Initiation |
| 4.18(iii) | (iii) showing the propagation and termination steps of the mechanism | Propagation Termination |
| 4.18(iv) | (iv) having limited use in synthesis because of further substitution reactions | The reaction does not stop at one substitution Other reasons for a mixture |