CLASS 10 IGCSE ORGANIC CHEMISTRY

Topic 1 – ORGANIC CHEMISTRY 1

Important Concepts Definitions and Formulae [CDF] material

Introduction
 Organic Chemistry is the scientific study of the structure,
properties, and reactions of organic compounds. Organic
compounds are those which contain carbon
 For conventional reasons metal carbonates, carbon dioxide and
carbon monoxide are not included in organic compound.

Definition of a hydrocarbon
 A compound that contains only hydrogen and carbon atoms
Combustion of hydrocarbons
 These compounds undergo complete and incomplete

combustion
 Complete combustion occurs when there is excess oxygen so

water and carbon dioxide form e.g:

CH4+ 2O2→CO2+ 2H2O
Read as “one mole of methane reacts with two moles of oxygen gas to form
one mole of carbon-dioxide and two moles of water”
 Incomplete combustion occurs when there is insufficient

oxygen to burn so either carbon monoxide and water or carbon

and water form e.g:
2CH4+ 3O2→ 2CO + 4H2O
CH4+ O2→ C + 2H2O
Names of compounds
 The names of organic compounds have two parts: the prefix or

stem and the end part (or suffix)

 The prefix tells you how many carbon atoms are present in the

longest continuous chain in the compound

 The suffix tells you what functional group is on the compound
Structures

Further rules for naming compounds

 When there is more than one carbon atom where a functional

group can be located it is important to distinguish exactly which

carbon the functional group is on
 Each carbon is numbered and these numbers are used to

describe where the functional group is

 When 2 functional groups are present di- is used as a prefix to

the second part of the name

 Branching also needs to be considered, the carbon atoms with

the branches are described by their number

 When the location of functional groups and branches needs to

be described the functional group takes precedence so the

functional group has the lowest number
Examples of branched molecules

Structures & Formulae of Alkanes

Formula: CnH2n+2 , n – number of carbons.
Alkenes
Formula: CnH2n

Alcohols “Hydrocabons
Hydrocabons having –OH group”
Formula: R-OH , where ‘R’ is an alkyl group.
Carboxylic acids- “Hydrocarbons
Hydrocarbons having –COOH group”
Formula: R-COOH.

Esters-“Hydrocarbons
Hydrocarbons having -COOR’ group”
Characteristics, Formula & Structural Isomerism
Functional group
 This is a group of atoms which are bonded in a specific

arrangement that is responsible for the characteristic reactions

of each member of a homologous series
series.
Names and structures of the functional groups

Structural isomers
 Compounds that have the same molecular formula but different

structural formulae
 This is due to the different arrangement of their atoms in space

 There are two types: chain and position

 In chain isomerism the structure of the carbon chain differs

 In position isomerism, the position of the functional group

differs
Example of chain isomerism

Example of position isomerism

The OH group position changes from 1 to 2

Position isomers of propanol: 1-propanol

1 or propan-1-ol
ol on the left and
propan-2-ol on the right.
Alkanes: Properties & Bonding
 A homologous series of hydrocarbon compounds with

only single carbon bonds, there are no C=C bonds present

 General formula of alkan
alkanes:
General Formula: CnH2n+2
 Alkanes are classified as saturated hydrocarbons as all the bonds

in alkanes are single bonds

 They are colourless compounds which have a gradual change in

their physical properties as the number of carbon atoms in the

chain increases
 Alkanes aree generally unreactive compounds but they do
undergo combustion reactions, can be cracked into smaller
molecules and react with halogens in the presence of light
 Methane is an alkane and is the major component of natural gas

 Methane undergoes complete comb combustion

ustion forming carbon
dioxide and water:
CH4 + 2O2 → CO2 + 2H2O
Substitution Reaction of Alkanes with Halogens
 In a substitution reaction, one atom is swapped with another

atom
 Alkanes undergo a substitution reaction with halogens in the

presence of ultraviolet radiation

Methane reacts with bromine gas to form bromo-methane

methane and hydrogen bromide

In the presence of ultraviolet (UV) radiation, methane reacts with bromine in

a substitution reaction.
Methane + Bromine → Bromomethane + Hydrogen Bromide
i.e. CH4 + Br2 → CH3Br + HBr
Alkenes: Catalytic Cracking & Distinguishing from Alkanes
 A homologous series of hydrocarbon compounds with carbon-
carbon
carbon double bonds (C = C)
 General formula:la:
General Formula: CnH2n
 All alkenes contain a double carbon bond, which is shown as

two lines between two of the carbon atoms

  This is the alkene functional group and is what allows alkenes to
react in ways that alkanes cannot
 Compounds that have a C=C double bond are also

called unsaturated compounds

The first three alkenes

Manufacture of alkenes and hydrogen

 Although there is use for each fraction obtained from the

fractional distillation of crude oil, the amount of longer chain

hydrocarbons produced is far greater than needed
 These long chain hydrocarbon molecules are further processed

to produce other products

 A process called catalytic cracking is used to convert longer-

chain molecules into short-chain and more useful hydrocarbons

 Alkenes and hydrogen are produced from the cracking of

alkanes
 Kerosene and diesel oil are often cracked to produce petrol,

other alkenes and hydrogen

Catalytic cracking explanation:
 Cracking allows large hydrocarbon molecules to be broken down

into smaller, more useful hydrocarbon molecules

 Fractions containing large hydrocarbon molecules are heated at

600 – 700°C to vaporise them

  Vapours will then pass over a hot catalyst of silica or alumina
 This process breaks covalent bonds in the molecules, causing
thermal decomposition reactions
 As a result, cracking produces smaller alkanes and alkenes. The
molecules are broken up in a random way which produce a
mixture of alkanes and alkenes
 Hydrogen and a higher proportion of alkenes are formed at
temperatures
atures of above 700ºC and higher pressure

The 10 carbon molecule decane is catalytically cracked to produce octane for petrol and ethene for ethanol

Distinguishing between alkanes and alkenes

 Alkanes and alkenes have different molecular structures

 All alkanes are saturated and alkenes are unsaturated

 The presence of the C=C double bond allows alkenes to react in

ways that alkanes cannot

 This allows us to tell alkenes apart from alkanes using a simple

chemical test:
Confirmation test for Alkene.
Alkene. Bromine water gets decolourised when
subjected to alkenes.

Test for Alkenes

Explanation:
 Bromine water is an orange coloured solution of bromine

 When bromine water is shaken with an Alkane, it will remain as

an orange solution as alkanes do not have double carbon bonds

(C=C) so the bromine remains in solution
 But when bromine water is shaken
shaken with an alkene, the alkene
will decolourise the bromine water and turn colourless as
alkenes do have double carbon bonds (C=C)
 The bromine atoms add across the C=C double bond hence the

solution no longer contains the orange coloured bromine

 This reaction
on between alkenes and bromine is called an addition
reaction
Addition Polymerisation
 Addition polymers are formed by the joining up of many small

molecules called monomers

 Addition polymerisation only occurs in monomers that contain

C=C bonds
 One of the bonds in each double bond breaks and forms a bond

with the adjacent monomer

 There are many types of polymers that are synthesized from

alkene monomers
 A common example is poly-ethene (polythene) which is the

addition of many ethene monomers

Polymerisation of ethene monomers to produce polythene

Further Addition Reactions

 Alkenes undergo additi
addition
on reactions in which atoms of a simple
molecule add across the C=C double bond
 The reaction between bromine and ethene is an example of an

addition reaction
 Bromine atoms add across the C=C in the addition reaction of ethene and bromine

 Alkenes also undergo addition reactions with hydrogen in which

an alkane is formed
 These are hydrogenation reactions and occur at 150ºC using
a nickel catalyst
 Hydrogenation reactions are used to change vegetable oils into
margarine to be sold in supermarkets

Hydrogen atoms add across the C=C in the hydrogenation of ethene to produce an alkane

 Alkenes also undergo addition reactions with steam in which

an alcohol is formed. SiSince
nce water is being added to the molecule
it is also called a hydration reaction
 The reaction is very important industrially for the production of
alcohols and it occurs using the following conditions:
o Temperature of around 330ºC

o Pressure of 60 – 70 atm

o Concentrated
centrated phosphoric acid catalyst
 A water molecule adds across the C=C in the hydration of ethene to produce ethanol

Alcohols
 Family of organic compounds that all contain the -OH functional
group
 This is the group of atoms responsible for their chemical
properties and reactions

Diagram showing the first three alcohols

Ethanol
Ethanol (C2H5OH) is one of the most important alcohols


 It is the type of alcohol found in alcoholic drinks such as wine

and beer
 It is also used as fuel for cars and as a solvent

 Alcohols burn in excess oxygen and produce CO2 and H2O

 Ethanol undergoes combustion:

CH3CH2OH + 3O2 → 2CO2 + 3H2O

The manufacture of ethanol
 There are two methods used to manufacture ethanol:

o The hydration of ethene with steam

o The fermentation of glucose

 Both methods have advantages and disadvantages which are
considered
Hydration of ethene
 A mixture of ethene and steam is passed over a hot catalyst

of phosphoric acid at a temperature of 330°C

 The pressure is used 60-70 atmosphere

 The gaseous ethanol is then condensed into a liquid for use

A water molecule adds across the C=C in the hydration of ethene to produce ethanol

Fermentation of glucose
 Sugar or starch is dissolved in water and yeast is added

 The mixture is then fermented between 15 and 35°C with

the absence of oxygen for a few days

 Yeast contains enzymes that break down starch or sugar to

glucose
 If the temperature is too low the reaction rate will be too slow

and if it is too high the enzymes will become denatured

 The yeast respire anaerobically using the glucose to form

ethanol and carbon dioxide:

C6H12O6 + Enzymes → 2CO2 + 2C2H5OH
 The yeast are killed off once the concentration of alcohol

reaches around 15%, hence the reaction vessel is emptied and

the process is started again
 This is the reason that ethanol production by fermentation is a

batch process