INTRO TO ORGANIC CHEMISTRY (2)

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CIE A Level Chemistry Your notes
3.1 An Introduction to AS Level Organic Chemistry

Contents
3.1.1 Hydrocarbons & Alkanes
3.1.2 Functional Groups and their Formulae
3.1.3 Naming of Organic Compounds
3.1.4 Molecular & Empirical Formulae
3.1.5 Characteristic Organic Reactions
3.1.6 Terminology Used in Reaction Mechanisms
3.1.7 Shapes of Organic Molecules; Sigma & Pi Bonds
3.1.8 Hybridisation in Organic Molecules
3.1.9 Planarity of Organic Molecules
3.1.10 Structural Isomerism
3.1.11 Stereoisomerism
3.1.12 Chirality
3.1.13 Isomers of Organic Compounds
Page 1 of 63
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3.1.1 Hydrocarbons & Alkanes

Your notes
Homologous Series
Organic chemistry is the chemistry of carbon compounds
Carbon forms a vast number of compounds because it can form strong covalent bonds with itself
This enables it to form long chains of carbon atoms, branched chains or cycles, and hence an almost
infinite variety of carbon compounds are known
Carbon always forms four covalent bonds which can be single, double or triple bonds
There is an almost infinite variety of chains, branches and rings able to form
A functional group is a specific atom or group of atoms which confer certain physical and chemical
properties onto the molecule
Organic molecules are classified by the dominant functional group on the molecule
Organic compounds with the same functional group, but with each successive member different by
CH2 are called a homologous series
Every time a carbon atom is added to the chain, two hydrogen atoms are also added, which is why
the successive members differ by CH2
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Hydrocarbons
Hydrocarbons are compounds that are made up of carbon and hydrogen atoms ONLY Your notes
The diagram shows examples of hydrocarbons

Ethanol is NOT a hydrocarbon as the molecule also contains an oxygen atom and is not solely made up of
carbon and hydrogen
Exam Tip
You must state that hydrocarbons are ‘only’ made up of C and H atoms if defining this term in an exam
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Alkanes
A functional group is an atom or a group of atoms in an organic molecule, which determines the Your notes
physical and chemical properties of the molecule
Alkanes are the simplest hydrocarbons with no functional group
They are made up of carbon and hydrogen atoms bonded to each other with single covalent bonds
Alkanes are compounds made up of carbon and hydrogen atoms only and contain no functional group
Homologous Series of Alkanes Table
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3.1.2 Functional Groups and their Formulae

Your notes
Functional Groups of Organic Compounds
Functional groups determine the physical and chemical properties of molecules
The table below shows a summary of common functional groups found in compounds
R is any other atom or group of atoms (except for hydrogen)
Functional groups found in compounds table
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Your notes
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Formulae of Organic Compounds

The general formula is a formula that represents a homologous series of compounds using letters and Your notes
numbers
Eg. the general formula of alkanes is CnH2n+2
A homologous series is a group of organic compounds that have the same functional group, the
same general formula and the same chemical properties
The structural formula is a formula that shows how the atoms are bonded to each carbon atom in a
molecule
The displayed formula is a 2D representation of an organic molecule showing all its atoms (by their
symbols) and their bonds (by single, double or triple bonds)
The skeletal formula is a simplified displayed formula with all the carbon and hydrogen (C-H) bonds
removed
Overview of the formulae of organic compounds table
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Worked example: Drawing skeletal formulae of molecules

Your notes
Worked example: Drawing displayed formulae of molecules
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Your notes
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3.1.3 Naming of Organic Compounds

Your notes
Nomenclature of Aliphatic Compounds
Systematic nomenclature can be used to name organic compounds and therefore make it easier to
refer to them
The alkanes provide the basis of the naming system and the stem of each name indicates how many
carbon atoms are in the longest chain in one molecule of the compound
Nomenclature of organic compounds table
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Your notes
If there are any side-chains or functional groups present, then the position of these groups are
indicated by numbering the carbon atoms in the longest chain starting at the end that gives the lowest
possible numbers in the name
The hydrocarbon side-chain is shown in brackets in the structural formula
CH3CH(CH3)CH2CH3
The side-chain is named by adding ‘-yl’ to the normal alkane stem
This type of group is called an alkyl group
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Your notes
If there are more than one of the same alkyl side-chain or functional groups, di- (for two), tri- (for three)
or tetra- (for four) is added in front of its name
The adjacent numbers have a comma between them
Numbers are separated from words by a hyphen
If there is more than one type of alkyl side-chain, they are listed in alphabetic order
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Your notes
Functional groups & their nomenclature table
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Your notes
Worked example: Naming organic molecules
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Your notes
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Exam Tip
Your notes
An aliphatic compound is straight or branched-chain and also includes cyclic organic compounds
that do not contain a benzene ring.
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3.1.4 Molecular & Empirical Formulae

Your notes
Molecular & Empirical Formulae of Organic Compounds
The molecular formula shows the number and type of each atom in a molecule
Eg. the molecular formula of ethanoic acid is C2H4O2
The empirical formula shows the simplest whole number ratio of the elements present in one molecule
of the compound
Eg. the empirical formula of ethanoic acid is CH2O
Worked example: Deducing molecular & empirical formulae
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Your notes
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3.1.5 Characteristic Organic Reactions

Your notes
Definitions & Terminology in Organic Chemistry
Homologous series
A homologous series is a group of organic compounds that have the same functional group, the same
general formula and the same chemical properties
Ethanol and propanol belong to the same homologous series

Saturated & unsaturated hydrocarbons
Saturated hydrocarbons are hydrocarbons which contain single bonds only resulting in the maximum
number of hydrogen atoms in the molecule
Unsaturated hydrocarbons are hydrocarbons which contain carbon-carbon double or triple bonds
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Your notes
The diagram shows saturated hydrocarbons which contain single bonds only and unsaturated
hydrocarbons which contain double/triple bonds as well
Homolytic & heterolytic fission
Homolytic fission is breaking a covalent bond in such a way that each atom takes an electron from the
bond to form two radicals
Heterolytic fission is breaking a covalent bond in such a way that the more electronegative atom takes
both the electrons from the bond to form a negative ion and leaving behind a positive ion
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Your notes
The diagram shows heterolytic fission in which the most electronegative atom takes both electrons in
the covalent bond and homolytic fission in which each atom takes one electron from the covalent bond
Radical chain reactions
A free radical is a species with one (or more than one) unpaired electrons
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The diagram shows a free radical which has one unpaired electron
A free radical reaction is a reaction involving free radicals and is a three-step reaction: Your notes
Initiation is the first step and involves breaking a covalent bond using energy from ultraviolet (UV)
light from the sun to form two free radicals
The propagation step is the second step in which the formed radical can attack reactant
molecules to form even more radicals
These in turn can again attack other molecules to form more free radical and so on
In the termination step, two free radicals react together to form a product molecule
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The diagram shows the different stages of a radical chain reactions

Nucleophiles & electrophiles Your notes
A nucleophile is an electron-rich species that can donate a pair of electrons
‘Nucleophile’ means ‘nucleus/positive charge loving’ as nucleophiles are attracted to positively
charged species
Nucleophilic refers to reactions that involve a nucleophile
An electrophile is an electron-deficient species that can accept a pair of electrons
‘Electrophile’ means ‘electron/negative charge loving’ as electrophiles are attracted to negatively
charged species
Electrophilic refers to reactions that involve an electrophile
A nucleophile ‘loves’ a positive charge and an electrophile ‘loves’ a negative charge

Types of reactions
An addition reaction is an organic reaction in which two (or more) molecules combine to give a single
product with no other products
A substitution reaction is a reaction that involves replacing an atom or group of atoms by another
An elimination reaction is a reaction in which a small molecule (such as H2O or HCl) is removed from an
organic molecule
A hydrolysis reaction is a reaction in which a compound is broken down by water (it can also refer to
the breakdown of a substance by dilute acids or alkali)
A condensation reaction is a reaction in which two organic molecules join together and in the process
eliminate small molecules (such as H2O or HCl)
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Your notes
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Your notes
The different types of reactions in organic chemistry

Oxidation & reduction
An oxidation reaction is a reaction in which oxygen is added, electrons are removed or the oxidation
number of a substance is increased
In organic chemistry it often refers to the addition of oxygen or removal of hydrogen atoms to a
substance
In equations for organic redox reactions, the symbol [O] can be used to represent one atom of
oxygen from an oxidising agent
A reduction reaction is a reaction in which oxygen is removed, electrons are added or the oxidation
number of a substance is decreased
In organic chemistry it often refers to the removal of oxygen or addition of hydrogen atoms to a
substance
In equations for organic redox reactions, the symbol [H] can be used to represent one atom of
hydrogen from a reducing agent
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Your notes
In organic chemistry oxidation is often the gain of oxygen or loss of hydrogen atoms and reduction is the
gain of hydrogen and loss of oxygen atoms
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3.1.6 Terminology Used in Reaction Mechanisms

Your notes
Terminology Used in Reaction Mechanisms
In organic reaction mechanisms, curly arrows represent the movement of electron pairs
The arrow begins at a bond or a lone pair of electrons and points to the species that accepts the lone
pair of electrons
Curly arrows show electron pairs moving from the source (eg. a nucleophile) to its destination (eg. an
electrophile)
Free-radical substitution
A free-radical substitution reaction is a reaction in which halogen atoms substitute for hydrogen
atoms in alkanes
It involves the initiation, propagation and termination steps
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Your notes
Example of a free-radical substitution reaction to form chloromethane from methane

Electrophilic addition
An electrophilic addition reaction is a reaction in which an electron rich region in a molecule is attacked
by an electrophile (a species that likes electrons/negative charge) followed by the addition of a small
molecule to give one product only
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Your notes
Example of an electrophilic addition reaction to form ethanol from ethene

Nucleophilic substitution
A nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile displaces a
halogen atom
The general nucleophilic substitution reaction mechanism

The C-X carbon of the halogenoalkane is electron deficient and has a δ+ charge
The halogen atom, X, is more electronegative than the carbon atom which means that it pulls
electrons towards itself and is δ–
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The nucleophile has a lone pair of electrons that it can donate to the δ+ carbon atom and form a
covalent bond
This causes the displacement of the halogen atom, X, which leaves as a halide ion, X– Your notes
The displaced halide ion is known as a leaving group
Nucleophilic addition
A nucleophilic addition reaction is a reaction in which a nucleophile (a species that likes a
nucleus/positive charge) attacks an electron-deficient region in a molecule followed by the addition
of a small molecule to give one product only
The general nucleophilic addition reaction mechanism
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3.1.7 Shapes of Organic Molecules; Sigma & Pi Bonds

Your notes
Straight, Branched & Cyclic Molecules
Straight, branched and cyclic organic molecules are also called aliphatic compounds as long as they
do not contain a benzene ring
Straight-chain
Straight-chain organic molecules are those in which the carbon atoms are connected to each other in
one continuous chain
Pentane is a straight-chain organic molecule as the carbon atoms are connected in a straight line
Branched
Branched organic molecules have side groups attached to the main chain of carbon atoms
2-methylbutane is a branched organic molecule as the main chain (consisting of 4 carbon atoms) has a
methyl branch
Cyclic
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Cyclic organic molecules are those in which the carbon atoms are connected to each other in a ring
shape
Your notes
Cyclopentane is a cyclic organic molecule as the carbons are attached to each other in a ring structure
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3.1.8 Hybridisation in Organic Molecules

Your notes
Hybridised Atoms: Shapes & Bond Angles in Molecules
Each carbon atom has four electrons in its outer shell (electronic configuration: 1s22s22p2)
Carbon atoms share these four electrons in four covalent bonds with other atoms to achieve a full
outer shell configuration
These electrons are found in orbitals within the respective atoms
When forming a covalent bond, the orbitals overlap in such a way to form two types of bonds
Sigma bonds (σ)
Pi bonds (π)
Hybridisation: sp3
The electron pair in a σ bond is found in a region of space between the nuclei of the two atoms that are
sharing the electrons
The electrostatic attraction between the electrons (negatively charged) and the two nuclei (positively
charged) holds the two atoms together
Carbon atoms that form four σ bonds are said to be sp3 hybridised
The four pairs of electrons around each carbon repel each other forcing the molecule to adopt a
configuration in which the bonding pairs of electrons are as far away from each other as possible
The molecule adopts a tetrahedral arrangement with bond angles of 109.5 o
The diagram shows a molecule of ethane in which each carbon atom forms four σ bonds to adopt a
tetrahedral configuration and minimise the repulsion between the bonding pairs of electrons
Hybridisation: sp2
When carbon atoms use only three of their electron pairs to form a σ bond, they are said to be sp2
hybridised
Each carbon atom will have a p orbital with contains one spare electron
When the p orbitals of two carbon atoms overlap with each other, a π bond is formed (the π bond
contains two electrons)
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The two orbitals that form the π bond lie above and below the plane of the two carbon atoms to
maximise bond overlap
The three bonding pair of electrons are in the plane of the molecule and repel each other Your notes
The molecule adopts a planar arrangement with bond angles of 120 o
The overlap of the two p orbitals results in the formation of a π bond in ethene (sp2 hybridised molecule)
in which the bonding pair of electrons repel each other to force the molecule into a planar configuration
with bond angles of 120 o
Hybridisation: sp
Carbon atoms can also use only one of their electron pair to form a σ bond, in which case the carbon
atoms are said to be sp hybridised
Each carbon atom will have two p orbitals with one spare electron each
When the four p orbitals of the carbon atoms overlap with each other, two π bonds are formed (each π
bond contains two electrons)
The two orbitals that form the π bond lie above and below the plane of the carbon atoms
The two orbitals of the other π bond lie in front and behind the plane of the atoms
This maximises the overlap of the four p orbitals
The molecule adopts a linear arrangement with bond angles 180 o
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Your notes
The overlap of the p orbitals results in the formation of two π bonds in ethyne (sp hybridised molecule)
which adopts a linear arrangement with bond angles of 180
Exam Tip
A double bond is a combination of a σ and π bond and a triple bond is a combination of one σ and two
π bonds.The strength of the bonds increases as follows: single < double < triple bondThis is due to the
increased electron density around the C-C atom, making the bond stronger and more difficult to
break.
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Hybridised Atoms: σ and π Bonds in Molecules

σ bonds Your notes
Sigma bonds are formed from the end-on overlap of atomic orbitals
S orbitals overlap this way as well as p orbitals
Sigma orbitals can be formed from the end-on overlap of s or p orbitals

The electron density in a σ bond is symmetrical about a line joining the nuclei of the atoms forming the
bond
The pair of electrons is found between the nuclei of the two atoms
The electrostatic attraction between the electrons and nuclei bonds the atoms to each other
The diagram below shows the arrangement of the σ bond in sp3, sp2 and sp hybridised carbon atoms
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Your notes
The σ orbitals are formed from the end-on overlap of the atomic orbitals resulting in symmetrical
electron density on the atoms
π bonds
Pi (π) bonds are formed from the sideways overlap of p orbitals

The two lobes that make up the π bond lie above and below the plane of the atoms
This maximises overlap of the p orbitals
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Your notes
π orbitals can be formed from the end-on overlap of p orbitals
In triple bonds, there is an additional overlap of p orbital

The two lobes of the π bond lie in front of and behind the plane of the atoms in the molecule
This maximises overlap of the p orbitals
The diagram below shows the arrangement of the π bond in sp3, sp2 and sp hybridised carbon atoms
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Your notes
The π orbitals are formed from the sideway overlap of the atomic orbitals
Exam Tip
π bonds are drawn as two electron clouds, one arising from each lobe of the p orbitals.The two clouds
of electrons in a π bond represent one bond consisting of two electrons (one from each orbital).
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3.1.9 Planarity of Organic Molecules

Your notes
Planar Molecules
Planar molecules have all their atoms in the same plane
Eg. linear, bent, trigonal planar and square planar
Molecules which have all their atoms in the same plane

The presence of an sp2 hybridised carbon can force the molecule to adopt a planar configuration
(trigonal planar)
The 3 σ bonds position themselves in a trigonal planar position so that the bonding pair of electrons are
as far away from each other and therefore minimise the repulsion between them
Eg. ethene
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Your notes
Ethene is a planar molecule with two trigonal planar centres around the carbon atoms
Eg. propene
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Your notes
Propene has two trigonal planar centres around the carbon-carbon double bond and one tetrahedral
centre
The presence of an sp hybridised carbon can also force the molecule to adopt a planar configuration
(linear)
The 2 σ bonds position themselves in a linear position to minimise the repulsion between the bonding
pairs of electrons
For example, ethyne
Ethyne is a planar molecule with one planar centre: the molecule is linear
Eg. propyne
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Your notes
Propyne has one planar centre around the carbon-carbon triple bond (linear) and one tetrahedral
centre
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3.1.10 Structural Isomerism

Your notes
Structural Isomerism: Chain, Position & Functional Group
Structural isomers are compounds that have the same molecular formula but different structural
formulae
Eg. propene and cyclopropane
Both propene and cyclopropane are made up of 3 carbon and 6 hydrogen atoms but the structure of the
two molecules differs
There are three different types of structural isomerism:

Chain isomerism
Positional isomerism
Functional group isomerism
Chain isomerism
Chain isomerism is when compounds have the same molecular formula, but their longest hydrocarbon
chain is not the same
This is caused by branching
Eg. pentane and 2,2-dimethylpropane
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Your notes
Both compounds are made up of the same atoms however the longest carbon chain in pentane is 5 and
in 2,2-dimethylpropane 3 (with two methyl branches)
Positional isomerism
Positional isomers arise from differences in the position of a functional group in each isomer
The functional group can be located on different carbons
For example, butanol and 2-butanol
Both compounds have an alcohol group and are made up of 4 carbon, 10 hydrogen and one oxygen
atom however in butanol the functional group is located on the first carbon and in 2-butanol on the
second carbon
Functional group isomerism
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When different functional groups result in the same molecular formula, functional group isomers arise
The isomers have very different chemical properties as they have different functional groups
For example, butanol and ethoxyethane Your notes
Both compounds have the same molecular formula however butanol contains an alcohol functional
group and ethoxyethane an ether functional group
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3.1.11 Stereoisomerism
Your notes
Stereoisomerism: Geometrical & Optical
What is stereoisomerism?
Stereoisomers are compounds that have the same atoms connected to each other, however the
atoms are differently arranged in space
There are two types of stereoisomerism:
Geometrical (cis/trans) isomerism
Optical isomerism
Types of stereoisomerism
Geometrical (cis/trans) isomerism
Geometrical isomerism is seen in unsaturated (double bond containing) or ring compounds that have
the same molecular formula and order of atoms (the atoms are connected similarly to each other) but
different shapes
Cis/trans nomenclature is used to distinguish between the isomers
Cis isomers have functional groups on the same side of the double bond/carbon ring
Trans isomers have functional groups on opposite sides of the double bond/carbon ring
Geometrical isomerism in unsaturated compounds
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Your notes
Geometrical isomerism in cyclic compounds
This causes the compounds to have different chemical and physical properties
For example, they may have different reaction rates for the same reaction (chemical property) or
different melting/boiling points (physical property)
Optical isomerism
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Optical isomers arise when a carbon atom in a molecule is bonded to four different atoms or groups of
atoms
The carbon atom is ‘asymmetric’ as there is no plane of symmetric in the molecule and is also called the Your notes
chiral centre of the molecule
The two different optical isomers are also called enantiomers
Just like the left hand cannot be superimposed on the right hand, enantiomers too are non-
superimposable
Enantiomers are mirror images of each other
Both molecules are made up of the same atoms which are bonded to each other identically, however
the chiral centre (carbon with four different groups) gives rise to optical isomerism
Optical isomers differ in their ability to rotate the plane of polarised light
One enantiomer will rotate it clockwise and the other anticlockwise
A2 only
Normal light is unpolarised and consists of electric and magnetic fields that vibrate at right angles to
each other in every possible direction
When the unpolarised light passes through a polariser, the light gets polarised causing it to vibrate in
only one plane
A pair of optical isomers will rotate the plane of polarised light by equal amounts in opposite direction
When equal amounts of the enantiomers are present in solution, the plane of polarised light doesn’t
change
As the enantiomers cancel out each other’s effect
A solution with equal amounts of both enantiomers is also called a racemic mixture
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Your notes
Light consists of vibrations in all possible directions however when it passes through a polariser the light
gets polarised and vibrates in only one plane: enantiomers cause the plane of polarised light to rotate
clockwise or anticlockwise
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Geometrical Isomerism in Alkenes

Unsaturated compounds Your notes
In unsaturated compounds, the groups attached to the C=C carbons remain fixed in their position
This is because free rotation of the bonds about the C=C bond is not possible due to the presence of a
π bond
The presence of a π bond in unsaturated compounds restricts rotation about the C=C bond forcing the
groups to remain fixed in their position and giving rise to the formation of geometrical isomers
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Exam Tip Your notes

Geometrical isomerism is also possible in cyclic compounds because there is limited rotation about
C-C single bonds that make up the rings.Therefore, the substitutions in cyclic compounds are fixed in
their position (to stay either above or below the ring of carbon atoms).
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3.1.12 Chirality
Your notes
Chirality & Enantiomers
Chiral centres in non-cyclic molecules
A chiral centre in a molecule is a carbon atom that has four different atoms or group of atoms attached
This gives rise to two optical isomers which are also called enantiomers
The enantiomers are mirror images of each other and cannot be superimposed
The presence of the chiral centre in the molecule allows two enantiomers to exist which are
stereoisomers as the molecules have the same atoms bonded to each other, but they are differently
arranged in space
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When the molecule contains more than one chiral centre (asymmetric carbon) more than two optical
isomers will be formed Your notes
If there are two chiral centres, each chiral centre will rotate the plane of polarised light clockwise
and anticlockwise
There are four possible optical isomers
Each chiral centre gives rise to two optical isomers; therefore, the molecule has a total of four optical
isomers
Chiral centres in cyclic molecules
To determine the chiral centre in a cyclic molecule, the carbon bonded to four different atoms or
groups of atoms should be found
Eg. 1,2-aminocyclohexanol has two chiral centres so it can form four optical isomers
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Your notes
To decide where the chiral centres are in a cyclic molecule, the carbon atoms bonded to four different
atoms or atom groups should be found
Exam Tip
Use a molecular modelling kit and make the models of enantiomers to help you understand that the
two molecules are non-superimposable and therefore non-identical.
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Identifying Chirality & Geometrical Isomerism

Identify chirality Your notes
Identifying chiral centres in cyclic and non-cyclic compounds is very straightforward as it is the carbon
with four different atoms or atom groups in a molecule
This gives rise to two optical isomers
When more than two chiral centres are present, more than two optical isomers exist
The maximum number of stereoisomers that a molecule can have is 2n, where n is the number of
chiral centres
So, a molecule with three chiral centres will have 23 = eight optical isomers
A molecule containing chiral centres is called a chiral molecule
Identifying geometrical isomers
Molecules with restricted rotation about the C-C bond can have geometrical isomers
This includes unsaturated and cyclic compounds
Eg. alkenes and cyclopentane
When the groups are positioned on the same side of the C-C double bond, the compound is a cis
isomer
When the groups are positioned on opposite sides of the C-C double bond the compound is a trans
isomer
Worked example: Drawing optical isomers
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Your notes
Worked example: Drawing geometrical isomers
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Your notes
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Your notes
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3.1.13 Isomers of Organic Compounds

Your notes
Deducing Isomers of a Compound
You should be able to deduce all possible isomers for organic compounds knowing their molecular
formula
Worked example: Isomers of dibromopropane
Answer
Step 1: Draw the structural formula of the compound
Step 2: Determine whether it is a stereo or structural isomer

There is no restricted bond rotation around the C-C bond, so it is structural isomerism
Step 3: Determine whether it is a functional group, chain or positional isomerism
Functional group? No, as Br is the only functional group possible
Chain? No, as the longest chain can only be 3
Positional? Yes, as the two bromine atoms can be bonded to different carbon atoms
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Your notes
Worked example: Deducing isomers of C4H10
Step 1: Draw the structural formula of the compound
Step 2: Determine whether it is a stereo or structural isomer.

There is no restricted bond rotation around the C-C bond and there is no chiral centre so it is structural
isomerism
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Step 3: Determine whether it is a functional group, chain or positional isomerism

Functional group? No, as there are no functional groups
Positional? No, as there are no functional groups which can be positioned on different carbon Your notes
atoms
Chain? Yes!
Worked example: Deducing isomers of C2H2Cl2
Step 1: Draw the possible structural formula of the compound
Page 62 of 63
Your notes
Step 2: Determine whether it is a stereo or structural isomer

The compound has to be unsaturated for it to have molecular formula C2H2Cl2 ; Due to the double bond
there is restricted rotation about the C-C bond; This compound will therefore display geometrical
isomerism
Step 3: Determine whether it is optical or geometrical isomerism
Optical? No, as there are no chiral centres
Geometric? Yes!
Page 63 of 63

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CIE A Level Chemistry Your notes

3.1 An Introduction to AS Level Organic Chemistry

3.1.1 Hydrocarbons & Alkanes

The diagram shows examples of hydrocarbons

3.1.2 Functional Groups and their Formulae

Formulae of Organic Compounds

Worked example: Drawing skeletal formulae of molecules

Worked example: Drawing displayed formulae of molecules

3.1.3 Naming of Organic Compounds

Functional groups & their nomenclature table

Worked example: Naming organic molecules

3.1.4 Molecular & Empirical Formulae

3.1.5 Characteristic Organic Reactions

Ethanol and propanol belong to the same homologous series

The diagram shows the different stages of a radical chain reactions

A nucleophile ‘loves’ a positive charge and an electrophile ‘loves’ a negative charge

The different types of reactions in organic chemistry

3.1.6 Terminology Used in Reaction Mechanisms

Example of a free-radical substitution reaction to form chloromethane from methane

Example of an electrophilic addition reaction to form ethanol from ethene

The general nucleophilic substitution reaction mechanism

The general nucleophilic addition reaction mechanism

3.1.7 Shapes of Organic Molecules; Sigma & Pi Bonds

3.1.8 Hybridisation in Organic Molecules

Hybridised Atoms: σ and π Bonds in Molecules

Sigma orbitals can be formed from the end-on overlap of s or p orbitals

Pi (π) bonds are formed from the sideways overlap of p orbitals

π orbitals can be formed from the end-on overlap of p orbitals

In triple bonds, there is an additional overlap of p orbital

3.1.9 Planarity of Organic Molecules

Molecules which have all their atoms in the same plane

3.1.10 Structural Isomerism

There are three different types of structural isomerism:

Geometrical isomerism in unsaturated compounds

Geometrical isomerism in cyclic compounds

Geometrical Isomerism in Alkenes

Exam Tip Your notes

Identifying Chirality & Geometrical Isomerism

Worked example: Drawing geometrical isomers

3.1.13 Isomers of Organic Compounds

Step 2: Determine whether it is a stereo or structural isomer

Worked example: Deducing isomers of C4H10

Step 1: Draw the structural formula of the compound

Step 2: Determine whether it is a stereo or structural isomer.

Step 3: Determine whether it is a functional group, chain or positional isomerism

Worked example: Deducing isomers of C2H2Cl2

Step 1: Draw the possible structural formula of the compound

Step 2: Determine whether it is a stereo or structural isomer

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