OCR A-Level Basic Concepts and Hydrocarbons

OCR A Chemistry A-level
Module 4.1: Basic Concepts and

Hydrocarbons
Detailed Notes
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4.1.1 Basic Concepts of Organic Chemistry
Naming and Representing the Formulae of Organic Compounds
Hydrocarbons
Organic chemistry mainly concerns the properties and reactions of hydrocarbons, compounds
that contain only carbon and hydrogen atoms. Hydrocarbons form series of compounds with
similar structures and formulas that can be represented in many different ways.
Nomenclature
Nomenclature is the set of rules that outline how different organic compounds should be named
and how their formulas are represented.
Naming compounds
Compounds are named according to rules laid out by the International Union of Pure and
Applied Chemistry (IUPAC). This ensures each compound is universally named the same -
which helps to avoid potentially dangerous confusion.
As well as being able to name compounds from their structures, you should be able to draw
structures from IUPAC names.
Stem
The prefix of the chemical tells you the length of the longest unbroken chain of carbon
atoms in the compound. The first 10 are given below, using alkanes as an example:
Functional groups
The ending (suffix) of the compound’s name tells you the functional group present. If there is
more than one functional group present, they are added as a prefix.
If a halogen is present, it is represented by a prefix:
Functional group Prefix
Fluorine Fluoro-
Chlorine Chloro-
Bromine Bromo-
Iodine Iodo-
Side chains
Carbon side chains that are branched from the longest carbon chain are represented by a
prefix at the start of the word. These alkyl groups are made using the stems given above
(meth-, eth-, prop-, etc), and the suffix -yl.
General rules
1. Functional groups and side chains are given, if necessary, with the number
corresponding to the carbon they are attached to.
2. Numbers are separated by commas.
3. Numbers and words are separated by hyphens.
4. If more than one particular side chain or functional group is present then one of the
following prefixes is added: di- (2), tri- (3), tetra- (4), etc.
5. The carbon chain is numbered in ascending order from the end of the chain nearest a
functional group.
6. If multiple prefixes are present, they are included in alphabetical order.
Examples
Example: The displayed structure of butan-2,3-diol.

This compound only has single carbon-carbon bonds, so is an alkane. Its longest chain of carbon atoms
is 4, giving the stem butan-, and it has two alcohol functional groups on carbons 2 and 3.
Example: The displayed structure of 3-ethyl,5-methylhexan-2-ol.
Example: The displayed structure of propanone.

Propan-2-one is also correct, but since the C=O can only be in the 2 position for the compound to be a
ketone, the number is not necessary.
Example: The skeletal structure of 1,2-dichloropropane
Formulas
There are many different ways of writing and representing organic compounds:
1. Empirical Formula
- The simplest whole number ratio of atoms of each element in a compound.
2. Molecular Formula
- The true number of atoms of each element in a compound.
3. General Formula
- The simplest algebraic formula of a member of a homologous series. All members of a
homologous organic series follow the general formula.
Example: Alkanes have the general formula CnH

2n+2.
4. Structural Formula
- The minimal detail that shows the arrangement of atoms in a molecule.
- The carboxyl group will be represented as COOH and the ester group as COO.
Example: The structural formula of 2-methylpropanoic acid is (CH3) 2CHCOOH.

5. Displayed Formula
- The relative positioning of atoms and the bonds between them. Shows every atom and
every bond in an organic compound.
Example:
6. Skeletal Formula
- The simplified organic formula of just a carbon skeleton and functional groups.
- Shows only the bonds in a compound and any non-carbon atoms.
- Vertices are carbon atoms.
- Hydrogen is assumed to be bonded to them unless stated otherwise.
Example:
7. Cyclic Compounds and Benzene
- These compounds are represented by the symbols below.
- Benzene can be represented in two equivalent ways.
Functional Groups
Homologous Series
A homologous series is a series of organic compounds with the same functional group but with
each successive member differing by CH2. Organic compounds are often part of a homologous
series, in which all members follow a general formula and react in a very similar way. There is
an increase in boiling points as the chain length increases.
Example:
Functional Group
Each homologous series has a functional group that allows that molecule to be recognised. A
functional group is a group of atoms responsible for the characteristic reactions of a
compound.
Example: Table of functional groups
Alkyl Group
An alkyl group is a hydrocarbon chain with the general formula C H₂ ₊₁. Sometimes R may
be used to represent alkyl groups, as well as other fragments of organic compounds not
involved in reactions.
Aliphatic
An aliphatic compound is a compound containing carbon and hydrogen joined together in
straight chains, branched chains or non-aromatic rings.
Alicyclic
An alicyclic compound is an aliphatic compound arranged in non-aromatic rings, with or
without side chains.
Aromatic
An aromatic compound is a compound containing a fully conjugated ring. Benzene is aromatic.
Saturated
A compound is described as being saturated if it contains single carbon-carbon bonds only.
Unsaturated
A compound is described as being unsaturated if it contains multiple carbon–carbon bonds,
including C=C, C≡C, and aromatic rings.
Isomerism
Isomers are molecules with the same molecular formula but a different arrangement of
atoms within the molecule. This gives the isomers a different structural formula.
Chain Isomers
Chain isomers have the same molecular formula but a different arrangement of the carbon
skeleton. The isomers’s carbon chain will differ - they can be straight chains or branched
chains, however they will always have the same molecular formula.
Example: Chain isomers with the molecular formula C4H10.
Position Isomers
Position isomers have the functional group of the molecule in a different position on the
carbon chain.
Example: Position isomers with the molecular formula C3H

8O
Functional Group Isomers

Functional group isomers have the same molecular formula, but the molecules have a different
functional group.
Example: Functional group isomers with the molecular formula C6H12
Reaction Mechanisms
Mechanisms
A ‘curly arrow’ is used to describe the movement of an electron pair during a reaction. It can
show either heterolytic fission or the formation of a covalent bond.
Example:
Breaking a covalent bond is called fission.
In homolytic fission, each bonding atom receives one electron from the bonded pair, forming
two radicals. Movement of one electron is shown by a single-headed curly arrow.
In heterolytic fission, one bonding atom receives both electrons from the bonded pair. This
leads to the formation of a positive and negative ion. Movement of two electrons is shown by
a double-headed curly arrow. Most mechanisms involve heterolytic fission.
A radical is a species with an unpaired electron. Radicals are represented by a dot, as shown
above in the homolytic fission of Cl₂.
Types of reactions
Reactions can be classified according to what happens to the reactants during the reaction and
what the end products are. The main types of reaction are:
● Addition - the reactants combine to form a single product.
● Substitution - one functional group is replaced by a different functional group.
● Oxidation - a species loses at least one electron, and is oxidised.
● Reduction - a species gains at least one electron, and is reduced.
● Polymerisation - a reaction in which many small molecules, known as monomers, join

together to form a long, repeating molecule called a polymer.
● Elimination - a small molecule is removed from a larger molecule.
4.1.2 Alkanes
Properties of Alkanes
Alkanes are saturated hydrocarbons containing single C-C and C-H bonds. These single
bonds are called σ bonds. The overlap of orbitals is directly between the two atoms and there is
free rotation around the σ bond.
Alkanes are part of a homologous series with the general formula CnH2n+2. Cycloalkanes are
an exception to this general formula but are still saturated hydrocarbons.
Each carbon atom in an alkane forms four σ bonds. They have tetrahedral geometry and a
bond angle of 109.5°. This shape minimises electron-electron repulsion between bonding pairs.
Variations in Boiling Points

Induced dipole-dipole interactions act between organic alkane chains and are affected by the
chain length and any branching. As the chain length of the alkane increases, so does the Mr
of the molecule. This results in stronger intermolecular forces between the chains and the
compound has a higher boiling point as a result.
Branching of alkane chains weakens van der Waals forces between the chains as they are less
able to pack tightly together. Therefore, the distance over which the intermolecular forces act is
increased and the attractive forces weakened. This means branched chain alkanes have
lower boiling points than straight chain alkanes.
Fractional distillation makes use of this variation in boiling points. The mixture of
hydrocarbons is vaporised and fed into the fractionating column. Vapours rise, cool and
condense at their different boiling points. The column is hotter at the bottom and cooler at the
top. Products with short carbon chains have lower boiling points, meaning they rise higher up
the column before reaching their boiling point. Therefore, they are collected at the top of the
column. Products with long carbon chains have higher boiling points, meaning they don’t rise
very far up the column before reaching their boiling point. They condense and are collected at
the bottom of the fractionating column.
Reactions of Alkanes
Alkanes have a low reactivity with many reagents due to the high bond enthalpy of the C-C
bonds and very low polarity of the σ-bonds present.
Combustion of Alkanes
Alkanes make good fuels as they release a lot of energy when burned. With sufficient
oxygen present, they undergo complete combustion to produce carbon dioxide and water.
Example:
If the oxygen present is insufficient, combustion is incomplete and carbon monoxide or

carbon particulates are produced alongside water.
Example:
Carbon monoxide is a toxic, gaseous product that is especially dangerous to humans as it is

odourless and colourless. Carbon monoxide is dangerous because it replaces oxygen in the
blood, starving the brain and other organs of oxygen and causing people to suffocate.
Oxides of nitrogen and sulfur are also produced as a byproduct of alkane combustion along
with carbon particulates from unburnt fuel. In clouds, these oxides can react with water and
form dilute acids, which result in acid rain.
Catalytic Converters
Oxides of nitrogen and carbon monoxide can be removed from systems using a catalytic
converter. This uses a rhodium catalyst to convert harmful products into more stable products
such as CO2, N2 or H2O.
Example:
Chlorination of Alkanes
Alkanes react with halogens in the presence of UV light to produce haloalkanes. The UV light
breaks down the halogen bonds (homolytic fission), producing reactive intermediates called free
radicals.
Free radicals are species containing an unpaired electron which is shown using a single dot.
These attack the alkanes, resulting in a series of reactions; initiation, propagation and
termination.
Example:
1. Initiation - The halogen-halogen bond is broken to form two free radicals.
Free radicals are shown using a dot
2. Propagation - In each propagation step, the molecule containing the radical changes
through single electron transfer. Overall, a hydrogen is replaced and the Cl• radical is
reformed as a catalyst.
3. Termination - Two radicals join to end the chain reaction and form a stable product.
The propagation step can continue many times to result in multiple substitutions - this is a
chain reaction. The conditions of the reaction can be altered to favour the termination step
and limit the number of substitutions, however, termination could also occur at different
positions in the carbon chain. The nature of this reaction to produce multiple products limits its
use in organic synthesis.
4.1.3 Alkenes
Properties of Alkenes
Introduction to Alkenes
Alkenes and cycloalkenes are unsaturated hydrocarbons with at least one carbon-carbon
double bond. They are part of a homologous series with the general formula CnH2n.
The carbon-carbon double bond is an area of high electron density, making it susceptible to
attack from electrophiles (species that are attracted to electron dense areas). It consists of a
normal covalent σ bond and a π bond.
The π-bond is formed by sideways overlap of adjacent p-orbitals above and below the
bonding C atoms. The σ-bond is formed by overlap of orbitals directly between the bonding
atoms.
Example:
The C-H bonds are in the same plane as the C-C σ bond. There is trigonal planar geometry
around the carbon atom and a bond angle of 120°. This angle minimises electron-electron
repulsion between bonding pairs. The π bond has electron density above and below the plane
of the 𝜎 bonds. There is restricted rotation in alkenes due to this π bond.
Bromine water is used to identify an alkene double bond and other unsaturated compounds.
Alkenes cause bromine water to change colour from orange-brown to colourless. This is
because bromine forms bonds to the carbon atoms, removing the C=C bond, causing the
compound to become saturated.
Stereoisomerism in Alkenes
Stereoisomers
Stereoisomers are compounds with the same structural formula but with a different
arrangement of atoms in space.
E-Z Isomerism
E-Z isomerism is a type of stereoisomerism, which occurs due to the limited rotation around
a double carbon bond. The limited rotation means that ‘high priority’ groups attached to the C=C
can either be ‘together’ or ‘opposite’. The E isomer has these groups apart on opposite sides
(one above, one below). The Z isomer has these groups together on the same side (both
above or both below).
Example:
Cahn-Ingold-Prelog (CIP) Priority Rules

There is a priority of different groups in molecules that can display E-Z isomerism. The atom
or group on each side of the double bond with the higher Ar or Mr is given the higher priority.
These high priority groups are used to determine if it is the E or Z isomer.
Example:
This molecule is the Z isomer as the highest priority

atoms are on the same side (both on top).
Cis-Trans Isomerism
Cis-trans iromerism is a special case of E/Z isomerism in which two of the substituent groups
attached to each carbon atom of the C=C group are the same. These stereoisomers can be
named in the same process as above, but instead using Cis- for when the groups are on the
same side and trans- for when they are different sides. It is important to remember that use of
E as equivalent to trans and Z as equivalent to cis is only consistently correct when there is an
H on each carbon atom of the C=C bond.
Addition Reactions of Alkenes
The carbon-carbon double bond in alkenes has a relatively low bond enthalpy. This makes
them relatively reactive. During their reactions, the double bond opens up to form single bonds
to other atoms. These are called addition reactions. The pi bond is an area of high electron
density. This attracts electrophiles.
Producing Alkanes
Alkenes can undergo electrophilic addition with hydrogen to produce alkanes. The C=C
bond opens up and forms single bonds to each of the hydrogen atoms. This reaction requires a
nickel catalyst.
Example:
This reaction is also known as a hydrogenation reaction. Catalytic hydrogenation is used in

the manufacture of margarine from unsaturated vegetable oils.
Producing Haloalkanes
Haloalkanes are organic compounds with single carbon bonds only and halogen functional
groups. Alkenes undergo addition reactions with halogens to form di-substituted
haloalkanes, and with hydrogen halides to form mono-substituted haloalkanes. The
electrophilic addition mechanism for this reaction is given on the following page of these notes.
Br₂ is present in bromine water in the test for unsaturation. This is an electrophilic addition
reaction, forming a dihaloalkane.
Producing Alcohols
Alcohols are organic compounds with a hydroxyl functional group, -OH. Alkenes undergo
addition reactions with steam to form alcohols. This reaction requires an acid catalyst, such
as phosphoric acid.
Example:
CH2CH2 + H2O → CH3CH2OH
Diols, alcohols with two hydroxyl functional groups, can also be formed from alkenes through
an oxidation reaction. The double bond is oxidised by acidified potassium manganate(VII)
(KMnO4). The manganate ions must be cold, dilute and acidified.
Example:
CH2CH2 + H2O + [O] → CH2(OH)CH2(OH)
Electrophilic Addition
Electrophiles
Electrophiles are electron pair acceptors and are attracted to areas of high electron density.
Some of the most common electrophile sources are:
● HBr
● Br2
● H2SO4
Electrophilic Addition
Electrophilic addition is the reaction mechanism that shows how electrophiles attack the double
bond in alkenes. When the double bond is broken, a carbocation intermediate forms. This is a
carbon atom with only three bonds, so it has a positive charge.
Carbocations can have varying stability, with tertiary being the most stable and primary the
least. The more stable the carbocation, the more likely it is to form. Therefore, in an addition
reaction of a hydrogen halide, multiple products can form but the major product will always be
the one that is formed via the most stable carbocation possible.
Mechanisms
Mechanism: alkene + halogen → dihaloalkane
Example: Electrophilic addition of bromine to ethene
The electron-rich π bond causes the bromine molecule to gain a temporary

dipole. This allows electrons to be transferred.
Mechanism: alkene + hydrogen halide → haloalkane
Example: Electrophilic addition of hydrogen bromide to ethene
There is a permanent dipole in HBr due to the electronegativity difference

between hydrogen and bromine.
Example: Electrophilic addition of hydrogen bromide to propene
Hydrogen bromide is polar due to the difference in the electronegativities of hydrogen and
bromine. The electron pair in the double bond transfers electrons to form a covalent σ bond to
H. This produces a positively charged carbocation intermediate on the other carbon, which
attracts the negatively charged bromide ion formed by cleavage of the H-Br bond in the first
step.
The hydrogen joins to the carbon atom which is bonded to the most hydrogen atoms. The
bromide ion bonds to the carbon atom which is joined to the most carbon atoms. This is due to
the tendency for the reaction to proceed via the most stable carbocation intermediate.
Hence, 2-bromopropane forms more often than 1-bromopropane in the mechanism of propene
with hydrogen bromide. This makes 2-bromopropane the major product.
Polymers from Alkenes
Addition Polymers
Addition polymers are produced from alkenes which are short chain monomers which join
together to form long chain polymers. The double bond of the alkene is broken to form a
repeating unit - the repetition of which would form the complete polymer chain.
Example: Addition polymerisation of ethene to form poly(ethene)
The repeating unit must always be shown with extended bonds through the brackets,
showing that it bonds to other units on both sides.
Waste Polymers and Alternatives
The energy and resources used to make polymers are large. Polymers are made from alkenes
which are obtained from crude oil, a non-renewable resource. The extraction and cracking of
crude oil are both high energy processes and additional energy is then needed to convert these
alkenes into polymers.
Uses of Polymers
Polymers are unreactive hydrocarbon chains with multiple strong, non-polar covalent
bonds. This makes them useful for manufacturing many everyday plastic products such as
poly(ethene) shopping bags.
However, the unreactive nature of the bonds in addition polymers means they are not
biodegradable and cannot be broken down by species in nature.
Benefits of using cheap oil-derived plastics are counteracted by problems for the environment if
these go to landfill. It is important to dispose of plastics effectively to improve the use of
resources and reduce the negative impact on the environment.
Disposal of Polymers
Addition polymers are non-biodegradable which means disposal of them can be difficult.
Waste polymers can be processed in different ways. Some can be recycled, some are used as
organic feedstock for production of plastics and other organic chemicals, and some are
combusted to produce energy for other industrial processes.
Combustion can release toxic gases which must be removed to reduce the impact on the
environment. During disposal by combustion of chlorine-containing haloalkanes, HCl may be
released. This is toxic and needs to be removed.
As well as this, scientists are developing biodegradable polymers and photodegradable

polymers to overcome these waste issues. This helps to reduce dependency on finite
resources and alleviates problems from disposal of persistent plastic waste.

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OCR A Chemistry A-level

Module 4.1: Basic Concepts and

This work by PMT Education is licensed under https://bit.ly/pmt-cc

Naming and Representing the Formulae of Organic Compounds

If a ​halogen ​is present, it is represented by a ​prefix​:

Functional group Prefix

Example: The displayed structure of butan-2,3-diol.

Example: The displayed structure of 3-ethyl,5-methylhexan-2-ol.

Example: The displayed structure of propanone.

Example: The skeletal structure of 1,2-dichloropropane

Example: Alkanes have the general formula C​nH

Example: The structural formula of 2-methylpropanoic acid is (CH​3)​ ​2CHCOOH.

Example: Table of functional groups

Example: Chain isomers with the molecular formula C​4​H​10.​

Example: Position isomers with the molecular formula C​3H

Functional Group Isomers

Example: Functional group isomers with the molecular formula C​6​H​12

Breaking a covalent bond is called​ fission​.

● Addition​ - the reactants combine to form a ​single product.

● Substitution​ - one functional group is ​replaced​ by a ​different functional group​.

● Oxidation​ - a species ​loses​ at least one electron, and is oxidised.

● Polymerisation​ - a reaction in which many small molecules, known as ​monomers,​ join

● Elimination​ - a small molecule is ​removed​ from a larger molecule.

Variations in Boiling Points

If the oxygen present is ​insufficient​, combustion is ​incomplete​ and ​carbon monoxide or

Carbon monoxide​ is a ​toxic​, gaseous product that is especially dangerous to humans as it is

1. Initiation​ - The halogen-halogen bond is broken to form two free radicals.

Free radicals are shown using a dot

Cahn-Ingold-Prelog (CIP) Priority Rules

This molecule is the Z isomer as the highest priority

Addition Reactions of Alkenes

This reaction is also known as a ​hydrogenation ​reaction. ​Catalytic hydrogenation​ is used in

CH​2​CH​2​ + H​2​O + [O] → CH​2​(OH)CH​2​(OH)

Mechanism: alkene + halogen → dihaloalkane

Example: Electrophilic addition of bromine to ethene

The electron-rich π bond causes the bromine molecule to gain a temporary

Mechanism: alkene + hydrogen halide → haloalkane

Example: Electrophilic addition of hydrogen bromide to ethene

There is a permanent dipole in HBr due to the electronegativity difference

Example: Electrophilic addition of hydrogen bromide to propene

Polymers from Alkenes

Example: Addition polymerisation of ethene to form poly(ethene)

As well as this, scientists are developing ​biodegradable polymers​ and​ photodegradable

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If a halogen is present, it is represented by a prefix:

Example: Alkanes have the general formula CnH

Example: The structural formula of 2-methylpropanoic acid is (CH3) 2CHCOOH.

Example: Chain isomers with the molecular formula C4H10.

Example: Position isomers with the molecular formula C3H

Example: Functional group isomers with the molecular formula C6H12

Breaking a covalent bond is called fission.

● Addition - the reactants combine to form a single product.

● Substitution - one functional group is replaced by a different functional group.

● Oxidation - a species loses at least one electron, and is oxidised.

● Polymerisation - a reaction in which many small molecules, known as monomers, join

● Elimination - a small molecule is removed from a larger molecule.

If the oxygen present is insufficient, combustion is incomplete and carbon monoxide or

Carbon monoxide is a toxic, gaseous product that is especially dangerous to humans as it is

1. Initiation - The halogen-halogen bond is broken to form two free radicals.

This reaction is also known as a hydrogenation reaction. Catalytic hydrogenation is used in

CH2CH2 + H2O + [O] → CH2(OH)CH2(OH)

As well as this, scientists are developing biodegradable polymers and photodegradable