AN INTRODUCTION TO

ORGANIC CHEMISTRY
A guide for A level students

KNOCKHARDY PUBLISHING
 KNOCKHARDY PUBLISHING

ORGANIC CHEMISTRY
INTRODUCTION
This Powerpoint show is one of several produced to help students understand
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ORGANIC CHEMISTRY
CONTENTS
• Scope of organic chemistry
• Special nature of carbon
• Types of formulae
• Homologous series
• Functional groups
• Nomenclature
• Investigating molecules
• Revision check list
 ORGANIC CHEMISTRY
Before you start it would be helpful to…

• Recall how covalent bonding arises

• Recall simple electron pair repulsion theory
 ORGANIC CHEMISTRY

Organic chemistry is the study of carbon compounds. It is such a complex branch of

chemistry because...

• CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER

• THE CARBON-CARBON BONDS CAN BE SINGLE, DOUBLE OR TRIPLE

• CARBON ATOMS CAN BE ARRANGED IN STRAIGHT CHAINS

BRANCHED CHAINS
and RINGS

• OTHER ATOMS/GROUPS OF ATOMS CAN BE PLACED ON THE CARBON ATOMS

• GROUPS CAN BE PLACED IN DIFFERENT POSITIONS ON A CARBON SKELETON

 SPECIAL NATURE OF CARBON - CATENATION
CATENATION is the ability to form bonds between atoms of the same element.
Carbon forms chains and rings, with single, double and triple covalent bonds, because it
is able to FORM STRONG COVALENT BONDS WITH OTHER CARBON ATOMS

Carbon forms a vast number of carbon compounds because of the strength of the C-C
covalent bond. Other Group IV elements can do it but their chemistry is limited due to the
weaker bond strength.

BOND ATOMIC RADIUS BOND ENTHALPY

C-C 0.077 nm +348 kJmol-1

Si-Si 0.117 nm +176 kJmol-1

The larger the atoms, the weaker the bond. Shielding due to filled inner orbitals and greater
distance from the nucleus means that the shared electron pair is held less strongly.
 THE SPECIAL NATURE OF CARBON

CHAINS AND RINGS

CARBON ATOMS CAN BE ARRANGED IN

STRAIGHT CHAINS

BRANCHED CHAINS

and RINGS

You can also get a combination of rings and chains

 THE SPECIAL NATURE OF CARBON

MULTIPLE BONDING AND SUBSTITUENTS

CARBON-CARBON COVALENT BONDS CAN BE SINGLE, DOUBLE OR TRIPLE

 THE SPECIAL NATURE OF CARBON

MULTIPLE BONDING AND SUBSTITUENTS

CARBON-CARBON COVALENT BONDS CAN BE SINGLE, DOUBLE OR TRIPLE

DIFFERENT ATOMS / GROUPS OF ATOMS CAN BE PLACED ON THE CARBONS

The basic atom is HYDROGEN but groups containing OXYGEN, NITROGEN,

HALOGENS and SULPHUR are very common.

CARBON SKELETON FUNCTIONAL CARBON SKELETON FUNCTIONAL

GROUP GROUP

The chemistry of an organic compound is determined by its FUNCTIONAL GROUP

 THE SPECIAL NATURE OF CARBON

MULTIPLE BONDING AND SUBSTITUENTS

ATOMS/GROUPS CAN BE PLACED IN DIFFERENT POSITIONS ON A CARBON SKELETON

THE C=C DOUBLE BOND IS IN A DIFFERENT POSITION

PENT-1-ENE PENT-2-ENE

THE CHLORINE ATOM IS IN A DIFFERENT POSITION

1-CHLOROBUTANE 2-CHLOROBUTANE
 TYPES OF FORMULAE - 1

MOLECULAR FORMULA C4H10

THE EXAMPLE BEING
The exact number of atoms of each
element present in the molecule USED IS... BUTANE

EMPIRICAL FORMULA C2H5

The simplest whole number ratio
of atoms in the molecule

STRUCTURAL FORMULA CH3CH2CH2CH3 CH3CH(CH3)CH3

The minimal detail using conventional
groups, for an unambiguous structure there are two possible structures

DISPLAYED FORMULA H H H H H H H
Shows both the relative placing of atoms H C C C C H H C C C H
and the number of bonds between them H H H H H H
H C H
H
 TYPES OF FORMULAE - 2

SKELETAL FORMULA
A skeletal formula is used to show a simplified organic formula by removing hydrogen
atoms from alkyl chains, leaving just a carbon skeleton and associated functional groups

CH2
CH2 CH2
for
CH2 CH2
CH2

CYCLOHEXANE THALIDOMIDE
 TYPES OF FORMULAE - 2

SKELETAL FORMULA
A skeletal formula is used to show a simplified organic formula by removing hydrogen
atoms from alkyl chains, leaving just a carbon skeleton and associated functional groups

CH2
CH2 CH2
for
CH2 CH2
CH2

CYCLOHEXANE THALIDOMIDE

GENERAL FORMULA
Represents any member of for alkanes it is... CnH2n+2
a homologous series possible formulae... CH4, C2H6 .... C99H200

The formula does not apply to cyclic compounds such as cyclohexane is C6H12
- by joining the atoms in a ring you need fewer H’s
 HOMOLOGOUS SERIES

A series of compounds of similar structure in which each member differs from the next
by a common repeating unit, CH2. Series members are called homologues and...

• all share the same general formula.

• formula of a homologue differs from its neighbour by CH2. (e.g. CH4, C2H6, ... etc )
• contain the same functional group
• have similar chemical properties.
• show a gradual change in physical properties as molar mass increases.
• can usually be prepared by similar methods.

ALCOHOLS - FIRST THREE MEMBERS OF THE SERIES

CH3OH C2H5OH C3H7OH

METHANOL ETHANOL PROPAN-1-OL
 FUNCTIONAL GROUPS

Organic chemistry is a vast subject so it is easier to split it into small sections for study.
This is done by studying compounds which behave in a similar way because they have
a particular atom, or group of atoms, FUNCTIONAL GROUP, in their structure.

Functional groups can consist of one atom, a group of atoms or multiple bonds between
carbon atoms.

Each functional group has its own distinctive properties which means that the
properties of a compound are governed by the functional group(s) in it.

H H H H H H H H H H
H C C C C C NH2 H C C C C C OH

H H H H H H H H H H
Carbon Functional Carbon Functional
skeleton Group = AMINE skeleton Group = ALCOHOL
 COMMON FUNCTIONAL GROUPS

GROUP ENDING GENERAL FORMULA EXAMPLE

ALKANE - ane RH C2H6 ethane

ALKENE - ene C2H4 ethene

ALKYNE - yne C2H2 ethyne

HALOALKANE halo - RX C2H5Cl chloroethane

ALCOHOL - ol ROH C2H5OH ethanol

ALDEHYDE -al RCHO CH3CHO ethanal

KETONE - one RCOR CH3COCH3 propanone

CARBOXYLIC ACID - oic acid RCOOH CH3COOH ethanoic acid

ACYL CHLORIDE - oyl chloride RCOCl CH3COCl ethanoyl chloride

AMIDE - amide RCONH2 CH3CONH2 ethanamide

ESTER - yl - oate RCOOR CH3COOCH3 methyl ethanoate

NITRILE - nitrile RCN CH3CN ethanenitrile

AMINE - amine RNH2 CH3NH2 methylamine

NITRO nitro- RNO2 CH3NO2 nitromethane

SULPHONIC ACID - sulphonic acid RSO3H C6H5SO3H benzene sulphonic acid

ETHER - oxy - ane ROR C2H5OC2H5 ethoxyethane

 COMMON FUNCTIONAL GROUPS

ALKANE CARBOXYLIC ACID

ALKENE

ALKYNE
ESTER
HALOALKANE

ACYL CHLORIDE
AMINE

NITRILE
AMIDE
ALCOHOL

ETHER
NITRO

ALDEHYDE

SULPHONIC ACID
KETONE
 HOW MANY STRUCTURES?

Draw legitimate structures for each molecular formula and classify each one according
to the functional group present. Not all the structures represent stable compounds.

carbon atoms have 4 covalent bonds surrounding them

oxygen atoms 2
nitrogen atoms 3
hydrogen 1
halogen atoms 1

C2H6 ONE

C3H7Br TWO

C4H8 FIVE - 3 with C=C and 2 ring compounds with all C-C’s

C2H6O TWO - 1 with C-O-C and 1 with C-O-H

C3H6O SIX - 2 with C=O, 2 with C=C and 2 with rings

C2H7N TWO

C2H4O2 SEVERAL - Only 2 are stable

C2H3N TWO
 HOW MANY STRUCTURES?

Draw legitimate structures for each molecular formula and classify each one according
to the functional group present. Not all the structures represent stable compounds.

carbon atoms have 4 covalent bonds surrounding them

oxygen atoms 2
nitrogen atoms 3
hydrogen 1
halogen atoms 1

C2H6 ONE

C3H7Br TWO

C4H8 FIVE - 3 with C=C and 2 ring compounds with all C-C’s

C2H6O TWO - 1 with C-O-C and 1 with C-O-H

C3H6O SIX - 2 with C=O, 2 with C=C and 2 with rings

C2H7N TWO

C2H4O2 SEVERAL - Only 2 are stable

C2H3N TWO
 NOMENCLATURE

Ideally a naming system should tell you everything about a structure without ambiguity.
There are two types of naming system commonly found in organic chemistry;

Trivial : based on some property or historical aspect;

the name tells you little about the structure
Systematic : based on an agreed set of rules (I.U.P.A.C);
exact structure can be found from the name (and vice-versa).

HOMOLOGOUS SERIES
trivial name systematic name example(s)
paraffin alkane methane, butane
olefin alkene ethene, butene
fatty acid alkanoic (carboxylic) acid ethanoic acid

INDIVIDUAL COMPOUNDS
trivial name derivation systematic name
methane methu = wine (Gk.) methane (CH4)
butane butyrum = butter (Lat.) butane (C4H10)
acetic acid acetum = vinegar (Lat.) ethanoic acid (CH3COOH)
 I.U.P.A.C. NOMENCLATURE
A systematic name has two main parts.

STEM number of carbon atoms in longest chain bearing the functional group +
a prefix showing the position and identity of any side-chain substituents.

Apart from the first four, which have trivial names, Prefix C atoms Alkane
the number of carbons atoms is indicated by a meth- 1 methane
prefix derived from the Greek numbering system. eth- 2 ethane
prop- 3 propane
but- 4 butane
The list of alkanes demonstrate the use of prefixes. pent- 5 pentane
hex- 6 hexane
The ending -ane is the same as they are all hept- 7 heptane
alkanes. oct- 8 octane
non- 9 nonane
dec- 10 decane

Working out which is the longest chain can pose a problem with larger molecules.
 I.U.P.A.C. NOMENCLATURE
How long is a chain?

Because organic molecules are three dimensional and paper is two dimensional it
can confusing when comparing molecules. This is because...

1. It is too complicated to draw molecules with the correct bond angles

2. Single covalent bonds are free to rotate

All the following written structures are of the same molecule - PENTANE C5H12

CH3
CH3 CH2 CH2 CH2 CH3
CH2 CH2 CH2 CH3
CH3
CH2 CH2 CH2 CH3 CH2 CH3
CH3 CH2 CH2

A simple way to check is to run a finger along the chain and see how many carbon
atoms can be covered without reversing direction or taking the finger off the page.
In all the above there are... FIVE CARBON ATOMS IN A LINE.
 I.U.P.A.C. NOMENCLATURE
How long is the longest chain?

Look at the structures and work out how many carbon atoms are in the longest chain.

CH3
THE ANSWERS ARE
CH2 ON THE NEXT SLIDE

CH3 CH CH2 CH3

CH3
CH3 CH2 CH2 CH2 CH CH3

CH3
CH3 CH2
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
How long is the longest chain?

Look at the structures and work out how many carbon atoms are in the longest chain.

CH3
CH2 LONGEST CHAIN = 5

CH3 CH CH2 CH3

CH3 LONGEST CHAIN = 6

CH3 CH2 CH2 CH2 CH CH3

CH3
CH3 CH2 LONGEST CHAIN = 6
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
A systematic name has two main parts.

SUFFIX An ending that tells you which functional group is present

See if any functional groups are present.

Add relevant ending to the basic stem. Functional group Suffix
ALKANE - ANE
ALKENE - ENE
In many cases the position of the functional
ALKYNE - YNE
group must be given to avoid any ambiguity
ALCOHOL - OL
ALDEHYDE - AL
KETONE - ONE
ACID - OIC ACID

1-CHLOROBUTANE 2-CHLOROBUTANE

SUBSTITUENTS Many compounds have substituents (additional atoms, or groups)

attached to the chain. Their position is numbered.
 I.U.P.A.C. NOMENCLATURE
SIDE-CHAIN carbon based substituents are named before the chain name.
they have the prefix -yl added to the basic stem (e.g. CH3 is methyl).

Alkyl radicals methyl CH3 - CH3

ethyl CH3- CH2- C2H5
propyl CH3- CH2- CH2- C3H7

Number the principal chain from one end to give the lowest numbers.
Side-chain names appear in alphabetical order butyl, ethyl, methyl, propyl
Each side-chain is given its own number.
If identical side-chains appear more than once, prefix with di, tri, tetra, penta, hexa
Numbers are separated from names by a HYPHEN e.g. 2-methylheptane
Numbers are separated from numbers by a COMMA e.g. 2,3-dimethylbutane
 I.U.P.A.C. NOMENCLATURE
SIDE-CHAIN carbon based substituents are named before the chain name.
they have the prefix -yl added to the basic stem (e.g. CH3 is methyl).

Alkyl radicals methyl CH3 - CH3

ethyl CH3- CH2- C2H5
propyl CH3- CH2- CH2- C3H7

Number the principal chain from one end to give the lowest numbers.
Side-chain names appear in alphabetical order butyl, ethyl, methyl, propyl
Each side-chain is given its own number.
If identical side-chains appear more than once, prefix with di, tri, tetra, penta, hexa
Numbers are separated from names by a HYPHEN e.g. 2-methylheptane
Numbers are separated from numbers by a COMMA e.g. 2,3-dimethylbutane

Example longest chain 8 (it is an octane)

CH3 CH3
3,4,6 are the numbers NOT 3,5,6
order is ethyl, methyl, propyl CH3 CH2 CH2 CH CH2
3-ethyl-5-methyl-4-propyloctane CH3 CH2 CH2 CH CH CH2 CH3
 I.U.P.A.C. NOMENCLATURE
Apply the rules and name these alkanes
THE ANSWERS ARE ON THE NEXT SLIDE

CH3
CH2
CH3 CH CH2 CH3

CH3
CH3 CH2 CH2 CH2 CH CH3

CH3
CH3 CH2
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
Apply the rules and name these alkanes

CH3
CH2
CH3 CH CH2 CH3

CH3
CH3 CH2 CH2 CH2 CH CH3

CH3
CH3 CH2
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
Apply the rules and name these alkanes

Longest chain = 5 so it is a pentane

CH3
A CH3, methyl, group is attached to the
CH2 third carbon from one end...
CH3 CH CH2 CH3 3-methylpentane

CH3
CH3 CH2 CH2 CH2 CH CH3

CH3
CH3 CH2
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
Apply the rules and name these alkanes

Longest chain = 5 so it is a pentane

CH3
A CH3, methyl, group is attached to the
CH2 third carbon from one end...
CH3 CH CH2 CH3 3-methylpentane

Longest chain = 6 so it is a hexane

CH3
A CH3, methyl, group is attached to the
CH3 CH2 CH2 CH2 CH CH3 second carbon from one end...
2-methylhexane

CH3
CH3 CH2
CH3 CH2 CH CH CH3
 I.U.P.A.C. NOMENCLATURE
Apply the rules and name these alkanes

Longest chain = 5 so it is a pentane

CH3
A CH3, methyl, group is attached to the
CH2 third carbon from one end...
CH3 CH CH2 CH3 3-methylpentane

Longest chain = 6 so it is a hexane

CH3
A CH3, methyl, group is attached to the
CH3 CH2 CH2 CH2 CH CH3 second carbon from one end...
2-methylhexane

Longest chain = 6 so it is a hexane

CH3
CH3, methyl, groups are attached to the
CH3 CH2 third and fourth carbon atoms
(whichever end you count from).
CH3 CH2 CH CH CH3
3,4-dimethylhexane
 NAMING ALKENES

Length In alkenes the principal chain is not always the longest chain
It must contain the double bond
the name ends in -ENE

Position Count from one end as with alkanes.

Indicated by the lower numbered carbon atom on one end of the C=C bond

5 4 3 2 1
CH3CH2CH=CHCH3 is pent-2-ene (NOT pent-3-ene)

Side-chain Similar to alkanes

position is based on the number allocated to the double bond

1 2 3 4 1 2 3 4
CH2 = CH(CH3)CH2CH3 CH2 = CHCH(CH3)CH3
2-methylbut-1-ene 3-methylbut-1-ene
 WHICH COMPOUND IS IT?

Elucidation of the structures of organic compounds - a brief summary

Organic chemistry is so vast that the identification of a compound can be involved. The
characterisation takes place in a series of stages (see below). Relatively large amounts
of substance were required to elucidate the structure but, with modern technology and
the use of electronic instrumentation, very small amounts are now required.

Elemental composition
One assumes that organic compounds contain carbon and hydrogen but it can be
proved by letting the compound undergo combustion. Carbon is converted to carbon
dioxide and hydrogen is converted to water.

Percentage composition by mass

Found by dividing the mass of an element present by the mass of the compound
present, then multiplying by 100. Elemental mass of C and H can be found by allowing
the substance to undergo complete combustion. From this one can find...

mass of carbon = 12/44 of the mass of CO2 produced

mass of hydrogen = 2/18 of the mass of H2O produced
 INVESTIGATING MOLECULES
Empirical formula
The simplest ratio of elements present in the substance. It is calculated by dividing the
mass or percentage mass of each element by its molar mass and finding the simplest
ratio between the answers. Empirical formula is converted to the molecular formula
using molecular mass.
 INVESTIGATING MOLECULES
Empirical formula
The simplest ratio of elements present in the substance. It is calculated by dividing the
mass or percentage mass of each element by its molar mass and finding the simplest
ratio between the answers. Empirical formula is converted to the molecular formula
using molecular mass.

Molecular mass
Traditionally found out using a variety of techniques such as ... volumetric analysis or
molar volume methods (Dumas, Victor-Meyer or gas syringe experiments). Mass
spectrometry is now used. The m/z value of the molecular ion and gives the molecular
mass. The fragmentation pattern gives information about the compound.
 INVESTIGATING MOLECULES
Empirical formula
The simplest ratio of elements present in the substance. It is calculated by dividing the
mass or percentage mass of each element by its molar mass and finding the simplest
ratio between the answers. Empirical formula is converted to the molecular formula
using molecular mass.

Molecular mass
Traditionally found out using a variety of techniques such as ... volumetric analysis or
molar volume methods (Dumas, Victor-Meyer or gas syringe experiments). Mass
spectrometry is now used. The m/z value of the molecular ion and gives the molecular
mass. The fragmentation pattern gives information about the compound.

Molecular formula
The molecular formula is an exact multiple of the empirical formula. Comparing the
molecular mass with the empirical mass allows one to find the true formula. e.g.
if the empirical formula is CH (relative mass = 13) and the molecular mass is 78
the molecular formula will be 78/13 or 6 times the empirical formula i.e. C6H6 .
 INVESTIGATING MOLECULES
Empirical formula
The simplest ratio of elements present in the substance. It is calculated by dividing the
mass or percentage mass of each element by its molar mass and finding the simplest
ratio between the answers. Empirical formula is converted to the molecular formula
using molecular mass.

Molecular mass
Traditionally found out using a variety of techniques such as ... volumetric analysis or
molar volume methods (Dumas, Victor-Meyer or gas syringe experiments). Mass
spectrometry is now used. The m/z value of the molecular ion and gives the molecular
mass. The fragmentation pattern gives information about the compound.

Molecular formula
The molecular formula is an exact multiple of the empirical formula. Comparing the
molecular mass with the empirical mass allows one to find the true formula. e.g.
if the empirical formula is CH (relative mass = 13) and the molecular mass is 78
the molecular formula will be 78/13 or 6 times the empirical formula i.e. C6H6 .

Structural formula
Because of the complexity of organic molecules, there can be more than one structure
for a given molecular formula. To work out the structure, different tests are carried out.
 INVESTIGATING MOLECULES
Empirical formula
The simplest ratio of elements present in the substance. It is calculated by dividing the
mass or percentage mass of each element by its molar mass and finding the simplest
ratio between the answers. Empirical formula is converted to the molecular formula
using molecular mass.

Molecular mass
Traditionally found out using a variety of techniques such as ... volumetric analysis or
molar volume methods (Dumas, Victor-Meyer or gas syringe experiments). Mass
spectrometry is now used. The m/z value of the molecular ion and gives the molecular
mass. The fragmentation pattern gives information about the compound.

Molecular formula
The molecular formula is an exact multiple of the empirical formula. Comparing the
molecular mass with the empirical mass allows one to find the true formula. e.g.
if the empirical formula is CH (relative mass = 13) and the molecular mass is 78
the molecular formula will be 78/13 or 6 times the empirical formula i.e. C6H6 .

Structural formula
Because of the complexity of organic molecules, there can be more than one structure
for a given molecular formula. To work out the structure, different tests are carried out.
 INVESTIGATING MOLECULES
Chemical Chemical reactions can identify the functional group(s) present.

Spectroscopy IR detects bond types due to absorbance of i.r. radiation

NMR gives information about the position and relative

numbers of hydrogen atoms present in a molecule

Confirmation By comparison of IR or NMR spectra and

mass spectrometry
 REVISION CHECK
What should you be able to do?

Recall and explain the reasons for the large number of carbon based compounds
Be able to write out possible structures for a given molecular formula
Recognize the presence of a particular functional group in a structure
Know the IUPAC rules for naming alkanes and alkenes
Be able to name given alkanes and alkenes when given the structure
Be able to write out the structure of an alkane or alkene when given its name
Recall the methods used to characterise organic molecules

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 AN INTRODUCTION TO
ORGANIC CHEMISTRY
THE END

© 2003 JONATHAN HOPTON & KNOCKHARDY PUBLISHING