ORGANIC CHEMISTRY

Organic chemistry is the chemistry of the compounds of carbon found in plants and animals
e.g. fats, oils, proteins etc.
HYDROCARBONS
Hydrocarbons are compounds containing hydrogen and carbon and no other element. CxHy.
The hydrocarbons are themselves classified into several types according to their structure.
ALKANES
The members of this group of hydrocarbons are distinguished by:
 Possessing the general molecular formula CnH2n+2
 All members ending with -ane
 All members differing from the next by CH2
 Physical properties of members changing (increasing) gradually as you go down the
group.
The following table gives the molecular formula and names of the alkanes.

Name Molecular Structural formula Condensed formula

formula
1 Metha CH4 H CH4
ne H C H
H
2 Ethane C2H6 H H CH3CH3
H C C H
H H
3 Propan C3H8 H H H CH3CH2CH3
e H C C C H
H H H
4 Butane C4H10 H H H H CH3CH2CH2CH3
H C C C C H
H H H H
5 Pentan C5H12 H H H H H CH3(CH2)3CH3
e H C C C C C H
H H H H H
6 Hexan C6H14
e
7 Heptan C7H16
e
8 Octane C8H18

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9 Nonan C9H20
e
10 Decan C10H22
e

NAMING ALKANES
1. Choose the longest continuous chain in the compound. This may not necessarily be
that part written horizontally. The compound as a whole is named after the parent
on branched alkane having the same number of carbon atoms as the longest
continuous chain chosen
2. Number the carbon atoms of the longest continuous chain such that the carbon
atoms containing constituents have small numbers as much as possible.
3. Name the constituents and indicate its position with the number of the carbon atom
to which it is attached. If the same substituent appears more than once add the
prefix di, tri, tetra…
4. Write the name of the compound as one word separate numbers from each other by
a comma and a number from a word by a hyphen.
HOMOLOGOUS SERIES
A homologous series is a group of compounds of similar structure in which each member
differs from the next by the presence of an additional –CH2 group. E.g. alkanes
1. All members conform to a general molecular formula e.g. for alkanes CnH2n+2,
alkenes CnH2n, alkanols CnH2n+1OH and alkanoic acids CnH2n+1CO2H.
2. Each member differs in molecular formula from the next by CH2 e.g. alkanes are:
CH4, C2H6, C3H8…
3. All members show similar chemical reactions though varying in vigor. e.g. all
alkanes burns in air and give substitution reactions with chlorine.
4. The physical properties of members change gradually in the same direction along
the series e.g. in alkanes boiling and freezing points rise (CH4, a gas, C5H12, a
liquid, C20H42 a solid at r.t.p.). also densities increase and solubility in water
decreases as the number of carbon atoms per molecule increases.
5. General methods of preparation are known which can be applied to any member of
the series.

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ISOMERISM
Isomerism is the occurrence of two or more compounds with the same molecular
formula, but different structural formula.
Isomers of the same formula have different physical and chemical properties
because of structural differences.

Isomers of molecular formula C4H10

H H H H H H H
H C C C C H H C C C H
H H H H H H
H C H
H
Properties and reactions of Methane
Physical properties
Methane is a colourless gas with no smell. It is almost insoluble in water and much
less dense than air in the same conditions.
Chemical reactions
1. Combustion . methane burns (or explodes) in air on the application of a
flame. It produces carbon dioxide and steam.
CH4(g) + 2O2(g) CO2(g) + 2H2O(g) ∆H = -890 Kj mol-1
Methane is the important constituent of natural gas which usually accompanies
Petroleum deposits. Natural gas is non-poisonous and has no smell.
2. Chlorine
A mixture of methane and chlorine explodes when placed in bright
sunlight.
CH4(g) + 2Cl2(g) CH3Cl(g) + HCl(g)
H H

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H C H + Cl- Cl H C Cl + H Cl
(monochloromethane)
H H
CH3Cl2(l) + Cl2(g) HCl(g) + CH2Cl2(l) (dichloromethane)
CH2Cl2(l) + Cl2(g) HCl(g) + CHCl3 (trichloromethane)
HCl3(l) + Cl2(g) HCl(g) + CCl4(l) (tetrachloromethane)
These are called substitution reactions because chlorine successively
replaces hydrogen in the methane molecule.
Cracking
When an alkane is heated with a catalyst, its molecule breaks into two
smaller molecules. One of these is a molecule of an alkane. The other
molecule has a double bond and is called an alkane.
e.g. C12H26(g) C10H22(g) + C2H4(g)
dodecane decane ethane
Cracking is very useful. It converts larger molecules from heavier, less
useful fractions into smaller molecules that are useful as gasoline. It also
produces alkenes which are very useful for making Petrochemicals.
THE ALKENES
The alkenes are another homologous series of general formula CnH2n e.g.
ethene C2H4 which is a gas at room temperature and pressure.
The alkanes have only single bonds in their molecules alkenes have a
double bond in their molecules and have names ending in -ene.
Alkanes are said to be saturated because no further atoms can be added.
Alkenes are unsaturated compounds because it is possible to break the
double bond and add extra atoms to the molecule.

Name Molecular Molecular structure Condensed formula

formula

1Ethene C2H4 H H CH2 CH2

C C
H H

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2Propene C3H6 H H H CH2 CHCH3
C C C H
H H

3Butene C4H8 H H H H CH2 CHCH2CH3

C C C C H
H H H

Industrial production of ethene

In industrial, ethene is produced by cracking the gas oil fraction from
distillation of petroleum. At 12 atm. Pressure and 5200C, alkanes in the
petrol range C5H12 – C9H20 are produced, together with ethene and possibly
other alkenes e.g.
C17H36(g) C8H18(g) + 3C2H4(g) + C3H6(g)
Properties and reactions of ethene
Physical properties
Ethene is gaseous at r.t.p., colourless, almost insoluble in water and slightly
less dense than air.
Chemical reactions
1. Combustion. Ethene burns in air if a light is applied with smoky
flame from unburnt carbon.
C2H4(g) + 3O2(g) 2CO2(g) + 2H2O(g)
It also burns in chlorine with a reddish flame, forming carbon.
C2H4(g) + 2Cl(g) 2C(s) + 4HCl(g)
2. Addition reaction: The double bond makes alkenes much more
reactive than alkanes, it tends to break open and join on to other
atoms. This kind of reaction is called an addition reaction. As a
result the ethene loses its double bond and becomes saturated.
a) Hydrogen. Ethene and hydrogen combine when passed over
a catalyst of heated nickel or platinum.
H H catalyst H H

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 C C + H2 H C C H
H H Ni or Pt H H
Margarine making. Addition reactions are used to make margarine
from vegetable oil. Vegetable oils are unsaturated with several
double bonds in their molecules. By reacting them with hydrogen
and a catalyst, they are made more saturated. This raises the boiling
point so the liquid oil becomes a solid fat margarine.
b) Chlorine or bromine. When chlorine at ordinary
temperature combines rapidly (in sunlight) to give an oily
liquid 1,2-dichloroethane.
H H H H
C C + Cl Cl H C C H
H H Cl Cl
The similar reaction with bromine vapour rapidly destroys
the reddish-brown colour of the vapour. This acts as a
distinguishing test between ethene and gaseous alkanes.
c) Potassium manganate(vii). Ethane reacts rapidly if shaken
with acidified potassium manganate(vii) solution. The
solution is decolorized being reduced to the manganate(ii)
salt. The ethene is converted to ethane-1,2-diol by water and
oxygen from the potassium manganate(vii).
H H H H
C C + H2O + [O] H C C H
H H O O
H H
d) Steam
Ethene + steam ethanol

Acid catalyst
H H H H
C C + HOH H C C H
H H H OH
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Polyethene
Polymers are organic chemicals with large molecules. They are made by joining together
(polymerizing) many small molecules called monomers.
Polythene is a simple example of a polymer. It is made by polymerizing ethene.

Monomer: H H H H H H H H
ethene C C + C C + C C + C C
H H H H H H H H
Polymer : H H H H H H H H
polyethene C C C C C C C C
H H H H H H H H
If ethene with a trace of oxygen present is pressurized to about 100 atmospheres and heated to
start the reaction it is polymerized to form polyethene. The polyethene produced by this
method is a low-density material which softens at around 1200C.
Polyethene is very resistant to the common types of chemical action and can be moulded into
a great variety of domestic and scientific article – buckets, bowls, bags, flexible containers,
funnels, wash bottles…
Polyethene is an addition polymer. There is only one monomer molecule and only one
product.
Plastics and fibres
Plastics such as polythene and PVC are synthetic polymers so are synthetic fibres such as
polyesters and nylon. The monomers in these synthetic polymers are made from crude oil.
Plastics and synthetic polymers are gradually replacing traditional materials like wood, metal
and natural fibres.
Synthetic polymers are cheaper and they can be made lighter and stronger and coloured.
Unlike natural materials they do not rot or get broken down by bacteria. They are not
biodegradable. This makes plastics a serious litter and waste product problem.
Another problem with plastics is that they usually burn quite easily. This makes them a fire
hazard. Some burning plastics give off poisonous fumes, which is an extra danger.
Disposal of plastics

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In the recent past much of plastic waste has been used to landfill disused quarries.
Incineration- schemes have been developed to use the heat generated for heating purposes.
Recycling- large quantities of black bags and sheeting are produced for resale.
Biodegradable plastics, as well as those polymers that degrade in sunlight (photodegradable)
have been developed.

THE ALKANOLS (ALCOHOLS)

The alkanols form a homologous series of general molecular formula CnH2n+1OH. The
hydroxyl group –OH, is the characteristic functional group of the alkanols.

Name Molecular formula Structural formula

1 Methanol CH3OH H
H C O H
H

2 Ethanol C2H5OH H H
H C C O H
H H

3 Propanol C3H7OH H H H
H C C C O H
H H H

4 Butanol C4H9OH H H H H
H C C C C O H
H H H H

Isomerism
Like other series alkanols exhibit Isomerism e.g. propanol, C3H7OH can have two structural
formulae.
H H H H H H
H C C C O H H C C C H
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 H H H H O H
H
Manufacture of Ethanol
1.By fermentation. The source of ethanol is starch e.g. sweet potatoes. They are cooked to
release the starch granules and then treated with malt (partially sprouting maize) for an hour at
600C. malt supplies an enzyme i.e. diastase. In these conditions, the starch is hydrolysed to a
sugar, maltose.
At room temperature, yeast is added. One of its enzymes maltose, catalyses the hydrolysis of
maltose to glucose.

Another enzyme of yeast, zymase catalyses the decomposition of glucose to ethanol and
carbon dioxide.
2.Hyration of Ethene. Ethene reacts with steam and a catalyst to produce ethanol.
C2H4 + H2O H3PO4 C2H5OH
Most Ethanol for industrial use and for fuel is made this way.
Uses of ethanol
1.As a solvent. Many things dissolve in ethanol. It is used as a solvent in perfumes to dissolve
fragrant oils, some paints and vanishes also contain ethanol. Many stains will dissolve in
ethanol.
2.As a fuel. Ethanol burns with a clean, hot flame. It is used a in sprit burners. Ethanol for this
purpose is sold a methylated spirits. Ethanol can be used to replace petrol as a fuel for motor
vehicles.
3.In alcoholic drinks. Beer, wine and spirits contain ethanol in varying amounts. Beer 4%,
wine 10%, spirit 40%.
4.Ethanol is a drug. In small quantities it makes people feel happy and sociable. In large
quantities it makes people drunk and unable to do things properly. It is a dangerous drug for
people who are driving motor vehicles.
5.As a preservative. Brandy can be added to cakes to prevent them rotting.
Properties of alkanols
Physical properties. Methanol and ethanol are liquids at room temperature and pressure,
volatile, colourless, possess a characteristic smell and a burning taste. They mix with water in
all proportions.

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Chemical reactions. Ethanol burns with a blue flame. If wine or beer is opened and left for a
few days, it turns to vinegar. The ethanol is oxidized to ethanoic acid. It is this acid that gives
vinegar its sharp taste.

THE ALKANOIC (CARBOXYLIC) ACIDS

O
The characteristics functional group is C O H
Alkanoic acids are named as if they are derived from alkane by replacement of one hydrogen
atom by the COOH group.

Methanoic acid HCOOH O

H C O H

Ethanol acid CH3COOH H O

H C C O H
H

Propanoic acid CH3CH2COOH H H O

H C C C O H
H H

Laboratory preparation of ethanoic acid

sodium dichromate
out

in

ethanol

water bath

CH3CH2OH + 2O CH3COOH + H2O

Ethanol from ethanoic acid

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 Dichromate
The above diagram is a reflux condenser because vapours from the flask condense and run
back into the flask.
Physical properties of ethanoic acid.
Ethanoic acid is a colourless liquid with a strong irritating smell. It is soluble in water and has
a sour taste. It burns and blisters the skin and remove warts. It is a weak acid.
Ester formation
CH3COOH(l) + C2H5OH(l) CH3COOC2H5(l) + H2O(l)
Ethanoic acid ethanol ethyl ethanoate water
A mixture of ethanoic acid and alkanol (ethanol) is boiled under reflux with a little
concentrated Sulphuric acid as a catalyst, produces an ester with water. This reaction is called
esterification.
The esters have a pleasant fruity smell and are used as food flavouring materials and in
perfumes. Some esters occur naturally and these are also sweet smelling. They include:
(a). Vegetable oils, palm oil, groundnut oil, cashew nut…
(b). animal fats. Hydrolysis
CH3COOC2H5(l) + H2O(l) CH3COOH(l) + C2H5OH(l)
The reaction can be reversed to recover the acid and alkanol again by hydrolysis.
Acid hydrolysis
In the acid hydrolysis case the products are the alkanol and acid from which the ester was
derived.
CH3COOC2H5(l) + H2O(l) CH3COOH(aq) + C2H5OH(aq)
Alkaline hydrolysis
In the alkaline case, the above reaction occurs and is then followed by the production of the
Sodium (or Potassium) salt of acid e.g. sodium ethanoate.
CH3COOH(aq) + NaOH(aq) CH3COONa(aq) + H2O(l)
The production of soap by boiling a fat or oil with aqueous Sodium hydroxide is alkaline
hydrolysis of an ester. The hydrolysis of any ester is called Saponification.
e.g. Fat Sodium hydroxide soap + glycerol
glycerol stearate sodium stearate
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H35C17 COOCH2 HO CH2
H35C17 COOCH + 3NaOH 3C17H35COO- Na+ + HO CH
H35C17 COOCH2 HO CH2
SYNTHETIC POLYMERS (Artificial)
Condensation polymers
Nylon is made by reacting two different chemicals together, unlike polyethene which is made
only from monomer units of ethene.
e.g. 1,6-diaminohexane + hexanedioic acid
H2N(CH2)6NH2 HOOC(CH2)4COOH
H2N(CH2)6NHOC(CH2)4COOH + H2O
Amide link

O
C N

Each time a reaction takes place a molecule of water is lost and because of this it is called
condensation polymerization. Because an amide link is formed during the polymerization,
nylon is known as a polyamide.
We can obtain different polymers with different properties if we carry out condensation
polymerization reactions between other monomer molecules.
e.g. ethane-1,2-diol + benzene -1,4-dicarboxylic acid
HO(CH2)2OH HOOC(C6H4)COOH + H2O
Terylene: HO(CH2)2OCO(C6H4)COOH + H2O
Ester link
O
C O
Terylene can be turned in yarn which can then be woven. Terylene clothing is generally softer
than nylon. Because an ester link is formed during the polymerization. Terylene is known as a
polyester.

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NATURAL POLYMERS
Carbohydrates
A starch molecule is produced by the combination of many molecules of glucose, C6H12O6,
with elimination of water molecules. Since this splitting out of water molecules is classed as
condensation and many molecule of glucose are involved, starch can be called a condensation
polymer of glucose. For this purpose, glucose can be written as HOC6H10O4OH. Letting
C6H10O4 be equal to
HO OH + HO OH + HO OH
O O O HO OH
Starch glucose
PETROLEUM
Petroleum (natural gas + crude oil) is the largest source of organic compounds. It is used
either as a fuel (source of energy) or for the synthesis of organic chemicals. Compounds
which contain carbon and hydrogen are called hydrocarbons.
Crude oil is separated into fractions before it can be useful. The separation of crude oil is done
by fractional distillation.
refined gas
steel fractionating
column gasoline

kerosene

heated crude oil diesel oil

residue (bitumen)

Fractions collected in an oil refined

Fraction Boiling range Carbon atoms uses

Refined gas Below room temp 1-4 Gaseous fuel, chemical

manufacture

Gasoline (petrol) 30 – 1600C 5 - 10 Motor car fuel, chemical

manufacture

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Kerosene (paraffin) 160-2500C 11 - 12 Heating fuel, jet fuel

Diesel oil 220 – 3500C 13 - 25 Diesel engine fuel for lorries,

trains etc.

Residue Above 3500C Over 25 Fuel for power stations, ships

etc. distilled further to give
lubricating oil, waxes, bitumen.

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