ORGANIC CHEMISTRY

Carbon: Organic Chemistry

• Carbon is an unusual atom in that it is able to
form very strong covalent bonds with other
carbon atoms.
• When we then include it’s ability to also bond
with other elements we open up the possibility
of the highly diverse and complex molecules
(like DNA) that have led to the possibility of life.
• Because of this, the chemistry of carbon
containing compounds is often called organic
chemistry.
Organic chemistry is the chemistry of carbon
containing compounds.
 Terms in organic chemistry
Hydrocarbon – a chemical that contains carbon
and hydrogen only
Homologous series – a group of chemicals that
have similar chemical properties.
Functional group – a bond or group of chemicals
that result in the similar properties in a
homologous series.
Representing Organic Compounds
There are 3 ways of representing organic
compounds
Chemical formula – very similar to inorganic
compounds but the functional group is often
written at the end and it can be written to
show bonding of each carbon
e.g. C2 H6 and C2 H5 OH and CH3 CH2 CH3
Dot-cross diagrams

H H

H
H
Structural formula – this shows the chemical
symbol of each atom in the chemical with its
bonding with other atoms.
If the atoms share a single electron there is one
line shown between them and if they share
two electrons there is a double line shown
between them.
 Methane, CH4
In the formula displayed we show these bonds as a
single line.
Each line is really a pair of shared electrons

H H
H

H C H C

H
H
H H

C C

H H
 Formula
• The carbon atoms are joined together by a
double bond.
• Its displayed formula may be drawn in slightly
different forms but should always clearly show
the double bond.

H H
H H
C C or
C C
H H
H H
 Naming Organic Compounds
Organic compounds are named in two parts.
The first part is named according to the number
of carbons in the longest chain of carbons.
The second part is named according to the
functional group.
 First part
One carbon – meth
Two carbons – eth
Three carbons – prop
Four carbons – but
Five - pent
The next five are named in the same way as
geometrical shapes
Six carbons – hex
Seven carbons – hept
Eight carbons – oct
Nine carbons – non
Ten carbons - dec
 Second part
Each homologous series is named according to
the functional group and the second part of
the name comes from this name.
Alkanes - are hydrocarbons with only single
bonds between carbons
Alkenes – are hydrocarbons with at least one
double bond between carbons.
Alkanols – have one of the hydrogen replaced by
the – OH group
Alkanoic acids have the following structure at
the end of each chain
O
-C
O H
Alkyl halides – at least one of the halogens is
replaced by a halogen
When naming an organic compound the alk-
part of the name of the homologous series is
replaced by the name relating to the number
of carbons.
ALKANES
These are hydrocarbons with single bonds.
Because each carbon has 4 single bonds and
cannot bond with anything else, alkanes are
known as saturated compounds.
The alkane with one carbon
Methane (CH4 )
The alkane with 2 carbons is
Ethane (C2 H 6 )
The alkane with 3 carbons is
Propane (C3 H8 )
The alkane with 4 carbons is known as
Butane (C4 H10 )
The alkane with 5 carbons is known as
Pentane (C5 H12 )
 Example of alkanes

Alkane with one carbon is methane

CH4

H H
H

H C H C

H
H
 Alkanes: Ethane, C2H6

• Ethane is the simplest alkane containing a C-

C single covalent bond.

H H

H H

H C C H H C C H

H H

H H
Activity

• Complete the diagram below including it’s electrons.

Carbon electron Hydrogen electron

H H H

H C C C H

H H H
 Alkanes
• The simplest hydrocarbons form a series of
compounds known as alkanes.
• These all consist of carbon and hydrogen only and
every carbon has four single covalent bonds.
Hydrocarbon Formula Structure

Methane CH4
hydrogen

Ethane C2H6 carbon

Propane C3H8

Butane C4H10
 Names of Alkanes
• The names of the 4 simplest alkanes are methane,
ethane, propane and butane.
• After that the names are systematic (like the words
used to describe geometric shapes.) E.g.
– 5 carbons = pentane C5H12
– 6 carbons = hexane C6H14
– 7 carbons = heptane C7H16
– 8 carbons = octane C8H18
– 9 carbons = nonane C9H20
– 10 carbons = decane C10H22
hydrogen
pentane
carbon
Each alkane has a CH3 at each end and an
increasing number of CH2 between them’
The relative atomic mass increases by 14
between successive alkanes
The general formula of alkanes is
Cn H2n+2
Activity

• What will be the formula for alkanes

containing the following numbers of
carbons?

Number of carbons Formula

12 C12H26

16 C16H34

31 C31H64

19 C19H40
 Formulae and Models of Alkanes
• Although normal chemical formula - like C5H12 -
are used to describe alkanes they do not convey
which atom is joined to which other atom.
• To get around this we often used displayed
formula to describe organic molecules.
• Displayed formula show which 4 atoms each
carbon is bonded to but even these do not show
the actual 3D shapes. For that we use models.
H

methane, CH4 H C H

H
Alkanes
H

H C H methane, CH4

H H

H C C H ethane, C2H6

H H

H H H

H C C C H propane, C3H8

H H H
 butane, C4H10

H H H H

H C C C C H

H H H H

pentane, C5H12

H H H H H

H C C C C C H

H H H H H
 H H H H H H
hexane, C6H14

H C C C C C C H

H H H H H H

Notice
the carbon chain
is not really
straight

and so on…………
 Physical Properties of Alkanes
1. They do not conduct electricity
2. They are not soluble in water
3. Their density, melting points and boiling
points increase as the size and molar mass of
the molecules increases.
At room temperature
Methane – gas
Ethane – gas
Propane – gas
Butane – gas
Pentane –liquid
Candelwax (C25 H52 ) - solid
Chemical reactions of alkanes
1. They are generally unreactive except for
combustion or burning.
When there is sufficient oxygen you have the
complete combustion of alkanes to give
carbon dioxide and water
e.g. CH4 + 3O2  CO2 + 2H2 O
2C2 H6 + 7O2  4CO2 + 6H2 O
When there is insufficient oxygen you get
incomplete combustion and get carbon and
carbon monoxide formed as well.
Incomplete Combustion of Alkanes

• In the absence of an adequate

supply of air, alkanes may react
to form carbon monoxide and
water.
• Carbon monoxide is highly
poisonous and this is one
reason why gas boilers must be
serviced regularly. A carbon
monoxide
detector

Methane + oxygen  water + carbon monoxide

2CH4 + 3O2  4H2O + 2CO

2. They also have substitution reactions where
one or more of the hydrogen is replaced by
another chemical. These reactions are
usually slow and need lots of energy added.
E.g. CH4 + Br2  CH3 Br + H Br
Alkenes
Alkenes have double bonds between at least
two carbon atoms. Because one of these
bonds can be broken and allow the carbon
atoms to join with something else alkenes are
known as unsaturated compounds.
An alkene with one carbon atom is
Impossible
An alkene with 2 carbon atoms is
Ethene (C2 H4 )
An alkene with 3 carbon atoms is
Propene (C3 H6 )
An alkene with 4 carbon atoms is
Butene (C4 H8 )
An alkene with 5 carbon atoms is
Pentene (C5H10 )
 Ethene - formula
• The simplest alkene is ethene.
• It has the formula C2H4
• The carbon atoms are joined together by a
double bond.
• Its displayed formula may be drawn in slightly
different forms but should always clearly show
the double bond.
H H
H H
C C or
C C
H H
H H
Activity

• Displayed formula for propene and butene are

shown.

H H H H
H C H C
C C H H C H
C C H
H H H H
 H H
H C
H C H
H H
C C H
H H
Pentene has formula C5 H10
The general formula for ethenes is
Cn H2n
Activity

• What will be the formula for alkenes

containing the following numbers of
carbons?

Number of carbons Formula

11 C11H22

13 C13H26

32 C32H64

21 C21H42
 Physical Properties of alkenes
1. They do not conduct electricity
2. They do not dissolve in water
3. Their density, melting point and boiling point
increase as the size and molar mass of the
molecules increases
At room temperature
Ethene – gas
Propene – gas
Butene - gas
Chemical properties of alkenes
Alkenes are far more reactive.
They take place in combustion and addition
reactions
(a) Combustion
Alkenes burn in sufficient oxygen to form
carbon dioxide and water only.
e.g. C2 H4 + 3O2  2CO2 + 2H2 O
2C3 H6 +9O2  6CO2 + 6H2 O
In insufficient oxygen they burn to form carbon
monoxide and carbon (soot) as well.
Alkenes are not usually used as fuels.
(b) Addition reactions
The main reaction of alkenes is the addition
reaction.
In the addition reaction two or more molecules
add together to form a single product.
In organic chemistry at least one of the reacting
molecules must be unsaturated and the
product is always saturated.
 TEST FOR SATURATED AND UNSATURATED
COMPOUNDS
1. Add bromine water to the compound
2. If the compound is unsaturated the bromine
water rapidly changes colour from brown to
colourless.
3. If the compound is saturated the bromine
water remains brown.
 Saturated or Unsaturated?
• Saturated means “full up”.
• Alkanes are saturated.
• Every carbon atom has already used all four of it’s
bonds to join to four other atoms. No other atoms
can be added.
• Alkenes are unsaturated.

• They have a double bond that could instead

become two single bonds. This means that other
atoms can be added. It is not “full up”.
• Alkenes are unsaturated and so extra atoms
can be added to alkene molecules.
• This forms the basis of a test to distinguish
between alkanes and alkenes.
• When bromine water is added to an alkane
nothing happens but when bromine is added
to an alkene the red colour of the bromine
disappears.

H H Br Br
C C + Br2  H C C H
H H H H
Bromine
loses this Gas red colourless
red colour
2. Addition reaction with hydrogen
This converts the alkene to the alkane

CH4 + H2  CH6
3. Addition with steam (N.B.)
This leads to the manufacture of an alkanol
C2 H4 + H2 O  C2 H5 OH
4. Polymerisation N.B.
In this process many small alkenes join
together to make a long chain alkane.
The small alkene is known as the monomer
The long alkane is known as the polymer
Polymers are commonly known as plastics
 Poly(e)thene
• One important reaction of alkenes involves the
joining together of alkene molecules.
H H H H H H H H H H
H H And
H C C C C C C C C C C lots
C C
H H H H H H H H H H more..
H H
1 2 3 4 5 thousands
This is called addition polymerisation and is written as:

H H Pressure H H poly(e)thene

n C C C C
high
H H temperature H H n
ethene catalyst
 Polypropene
• Ethene is only one alkene. Other unsaturated
molecules such as propene, vinyl chloride and
styrene can also be polymerised to produce a
range of plastics. E.g. propene

H H H CH3
n H C Poly(propene)
C C H C C
H H H H n
propene
 PTFE
• Tetrafluoroethane is another alkene that is made
into an important plastic used to coat non-stick
pans: polytetrafluoroethane or PTFE.

F F
F F
n C C C C
F F F F n

tetrafluoroethene Poly(tetrafluoroethane)
or PTFE
Activity

• Fill in the products that will be obtained from

vinyl chloride

H Cl
n
H Cl C C
C C H H
H H n

pvc
Vinyl chloride
 Some uses of plastics

Poly(e)thene Polypropene Polystyrene

Shopping bags Milk crates packing
Bottles Rope insulation
Buckets Carpet fibres Ball pens
Washing up bowls
Alkenes are very useful as they are used as the
starting product of many chemicals including
polymers (plastics) and alcohols.
 Catalytic Cracking
One of the main methods of obtaining alkenes is
by catalytic cracking.
Catalytic cracking is the breaking of large alkane
molecules into one or more alkenes and a
smaller alkane by heat and in the presence of
a catalyst.
 Alkenes Sources
• Crude oil contains many large molecules.
• If these are to be used as fuels or feedstock for
the chemical industry then they have to be broken
down (or cracked) into smaller molecules.
Small molecules

Big molecules
Medium
molecules

Fuel gas Petrol

Naphtha Kerosine
Diesel Fuel Oil and bitumen
 Catalytic Cracking
• Large hydrocarbons are broken into smaller
molecules using heat and a catalyst.
• This process is known as catalytic cracking.
• The small molecules produced are then separated
by distillation.
Distillation
tower
pressure

Smaller molecules
Catalytic
Heat to cracker
Big Molecules
vaporise
Molecules break
up
 Catalytic Cracking
• In the catalytic cracker long chain molecules are
split apart or ‘cracked’. An example of such a
reaction is:
H H H H H H H H Octane
H C C C C C C C C H
H H H H H H H H
Heat
hexane catalyst
pressure

H H H H H H H H ethene
H C C C C C C H + C C
Ethene
H H
Used as a H H H H H H is used
fuel to make
C8H18  C6H14 + C2H4 plastics
C8 H18  C6 H14 + C2 H4
Activity

• Draw out displayed formulae of a pair of products

formed by cracking decane
H H H H H H H H H H
decane
H C C C C C C C C C C H

H H H H H H H H H H

Heat
catalyst
pressure

H H H H H H H H H H
H C C C C C C C C H + C C
H H H H
H H
H H H H
ethene
octane
C10 H22  C8 H18 + C2 H4
Activity

• Copy the Table and complete the empty boxes.

Number Name Alkane or Formula

of alkene
carbons
5 pentene alkene C5H10

8 octane alkane C8H18

4 butene alkene C4 H 8

10 decane alkane C10H22

Which of these is an alkane?
A. C6H14
B. C4H8
C. C12H24
D. C102H204
Which of these is a true statement about
alkenes?

A. They turn bromine water from colourless to

red
B. They contain a double bond
C. The smallest alkene has 1 carbon atom
D. They have names that end in “ane.”
Which of these is a true statement about
cracking?

A. it is the separation of molecules into

fractions of different sizes.
B. it is carried out at low temperatures
C. it uses a catalyst.
D. It produces polymers
Which of these is a true statement about
polymerisation?

A.it is the joining together of many small

molecules.
B. it is the thermal decomposition of plastics
C.it is carried out using saturated molecules
D.it is a multiplication reaction
Which of these is an addition polymer?

A. styrene
B. ethene
C. p.v.c.
D. propane
How might you test to see if polystyrene still
contained some unsaturated monomer (styrene)?

A. Crush it up and burn it.

B. Crush it up and add it to bromine water
C. Crush it up and dissolve it in petrol
D. Crush it up and add hydrochloric acid
Alkanols - the OH group is always written at the end of
the chemical formula but could occur on any carbon.
Methanol – CH3 OH
Ethanol - C2 H5 OH
Propanol - C3 H7 OH
Butanol - C4 H 9 OH
Pentanol - C5 H9 OH
 Methanol

H C OH

H
 Ethanol

H OH

H C C H

H H
 Propanol

H H OH

H C C C H

H H H
 Properties of alkanols
Alkanols are liquids at room temperature.
All alkanols will burn in oxygen to produce
carbon dioxide and water.
All alkanols can be used as a solvent for covalent
compounds.
However the alkanol you need to know is
ethanol
 Ethanol
Ethanol (C2 H5 OH) is a very useful chemical.
It can be used
1 . As a fuel (e.g. in blend petrol etc)
2. As a solvent (used in some medications etc)
3. In alcoholic beverages.
It can be manufactured industrially in two ways
- By fermentation
- By addition reaction of steam and ethene
Fermentation This is the anaerobic (no oxygen
present) breakdown of sugar by yeast.
You need a source of sugar (sugar cane, grapes
etc) and yeast in a sealed container so air
cannot enter.
The temperature must be controlled as if it is
too low the reaction is too slow and if it is too
high the yeast is killed (denatured)
Once the process is complete pure alcohol is
obtained by fractional distillation.
Addition reaction of ethene and steam
Steam and ethene are mixed at a high pressure
and temperature in the presence of the
catalyst Phosphoric acid.
C2 H4 + H2 O (g)  C2 H5 OH
As not all the steam is used up the pure alcohol
is obtained by fractional distillation,.
Alcohols can be oxidised to become alkanoic
acids.
Ethanol becomes ethanoic acid (vinegar)
C2 H5 OH + O2  CH3 COOH + H2 O
 Alkanoic acids
Alkanoic acids are weak acids that have the same
properties as all acids.
1. They have a pH of less than 7
2. They react with reactive metals to give a salt and
hydrogen only
3. They react with bases or alkalis to give a salt and
water only.
4. They react with carbonated to give a salt, water
and carbon dioxide.
In alkanoic acids the H of the COOH part of the
chemical is ionically bonded to the rest of the
chemical which is covalently bonded. This H is
the one that breaks off and forms the H+ ion
of the acid and is replaced in reactions.
C2 H 5 COOH + NaOH  C2 H5 COONa + H2 O
The alkanoic acids have – COOH at end. NB Be
careful to count the C in COOH when naming
the compound.
Methanoic acid HCOOH
Ethanoic acid CH3 COOH
Propanoic acid C2 H5 COOH
Butanoic acid C3 H7 COOH
Methanoic Acid

H C

0 H
 Ethanoic Acid

H 0

H C C

H O H
Alkyl halides
The number of carbons determines what replaces
the alk
e.g. Methyl chloride – CH3 Cl
Propyl bromide C3 H7 Br
Pentyl iodide C5 H11 I
 ETHYL CHLORIDE

H Cl

H C C H

H H
A fuel is a substance that burns in oxygen to give
energy.
Coal, natural gas and petroleum are all fuels
Natural gas is obtained from under ground.
Its main constituent is methane
Petroleum is a mixture of hydrocarbons and is
also obtained from underground.
It is separated into useful fractions by fractional
distillation.
(Petroleum is sometimes referred to as crude
oil)
The importance of oil

• These hydrocarbons are vital

to our way of life.
• We use them as highly
portable fuels for many forms
of transport.
• We also use them as raw
materials from which a huge
range of useful everyday
substances are made.
Making oil useful

• Although we can get useful substances from oil,

crude oil itself has no uses.
• In order to make crude oil into useful substances we
first have to separate the mixture into molecules of
similar size.
• This is done in an oil refinery.
Fractional Distillation

c
• Crude oil is split into fractions o
containing similar sized molecules o
using fractional distillation. l
• The oil is heated until it vaporises.
• It then passes up a tall tower that is
hot at the bottom but cool at the top.
• As the vapour passes up this tower
the molecules cool and condense
back to liquid. h
o
t
The boiling points of molecules

We have already said that, in general, the bigger

the molecule the higher the boiling point.
350
300
250 
200 B.Pt
(oC)
150
100
50 No. Carbon atoms 

0
0 5 10 15 20
Here are the boiling ranges of some fractions
obtained from distillation of petroleum

Fraction Boiling Number of

Range carbons
(oC)
Fuel gas Below 40 1-5
Petrol 40 - 175 5-10
Kerosine 150 - 240
9-14
Diesel 220 - 275
13-17
The flammability of molecules

• When hydrocarbons burn they are reacting

with oxygen in the air.

• In general, the smaller the molecule the

better it will mix and then react with the air.
• Flash points are (roughly) the temperature below
which you cannot ignite the substance.
• Here is some flash points data for oil fractions.
Link the molecule to the flash point.

Substance Flash Point

Kerosine <23
Petrol 85 - 150
Fuel Oil 23 - 61
The viscosity of molecules

• When we pour a liquid the molecules have to

pass each other. The easier they do this, the
runnier the liquid is.

• The molecules in fuel oil and bitumen may

contain up to 400 carbon atoms in long chain
structures.

• These chains easily become entangled

reducing the runniness of the liquid and so
those made up of big molecules tend to be
viscous (treacly) not runny.
Here are the viscosities of 5 hydrocarbons.
The higher the value the less runny the hydrocarbon is.
Draw arrows joining the hydrocarbon with the
appropriate value.

Hydrocarbon Viscosity (cP)

Pentane - C5H12 0.40
Hexane - C6H12 0.52
Heptane - C7H16 0.24
Octane - C8H18 0.92
Decane - C10H22 0.70
The colour of molecules
• Small hydrocarbon molecules are gases or
transparent liquids.
• As the molecules get larger the colour becomes
increasingly yellow through to the brown/black
colour of bitumen used on roads and roof repairs.

Increasing size of molecules 

The composition of fractions?

• We already know that each petroleum fraction consist

of hydrocarbon molecules falling within a particular
size range.

• The proportions of the different hydrocarbons present

in oil can vary greatly across the world.

• It is therefore not surprising that the exact nature of

the fractions collected will vary both in amount and
detailed composition.

• Nonetheless most crude oil will give rise to some

quantity of each type of fraction.
Uses of each fraction

Burned in the refinery to fuel the distillation

Fuel gas
process, sold as LPG, purified and sold as bottled
camping gas
Petrol
/ gasoline Fuel for cars and motorcycles, also used to make
chemicals.
Naphtha Used to make chemicals.
Paraffin /
Fuel for greenhouse heaters and jet engines,
Kerosine
manufacture of chemicals.
Diesel fuel Fuel for lorries, trains.
Fuel and
lubricating Fuel for the heating systems of large buildings, fuel
oil for ships, lubricating oil.

Bitumen Roofing, and road surfaces.

Which is a correct statement about crude oil?

A. A mixture of carbohydrates.
B. Formed by the decay of dead sea
creatures.
C. Consist of a mixture of very large
molecules.
D. Is purified in an oil rig.
Fuel gas is known as refinery gas.
Which is a correct statement about fractional
distillation?
A. Oil is separated into fractions with the same
size molecule.
B. Oil is separated into fractions with the same
density.
C. Oil is separated into fractions with similar
size molecules.
D. Oil is separated into alkanes and alkenes.
Which is a correct order for these fractions
working down from the top of the column?

A. Fuel gas, kerosine, petrol, diesel, bitumen.

B. Fuel gas, diesel, kerosine, petrol, bitumen.
C. Fuel gas, petrol, diesel, kerosine, bitumen.
D. Fuel gas, petrol, kerosine, diesel, bitumen.
Which of these is a true statement about the
changes that occur as hydrocarbon molecules
get larger?

A.Boiling point decreases.

B.Viscosity increases.
C.Flammability increases.
D.Transparency increases.
 ISOMERS
Isomers are organic chemicals that have the
same chemical formula but different structural
formula.
 Isomerism
Alkanes of the same formula can have different
arrangements of atoms. Such different arrangments are
known as isomers.
Two isomers of C4H10 are shown
H H H

H H H H H C C C H

H C C C C H H H

H H H H H C H

Isomers of butane
H