s.3 Chemistry Notes Organic Chem Continuation
s.3 Chemistry Notes Organic Chem Continuation
2. It can form a ring of carbon atoms. The compounds that form rings of carbon atoms
are alicyclic compounds.
Because of these two unique behaviours, carbon can form very many and complex
compounds which has made it necessary for its study under a separate branch called
organic chemistry. However, for historical and conventional reasons some simpler
compounds such as carbon dioxide (CO2 ) and sodium carbonate (Na2CO3 ) are usually studied
under non-carbon compound in inorganic chemistry.
Functional groups are groups of atoms that are common to a given homologous series and
are responsible for chemical reactions. Examples of functional groups include:
Homologous series
This is a series of organic compounds related to each other by the same functional group.
Characteristics of homologous series include:
i) All members conform to a general molecular formula e.g.
CnH 2n+2 for alkanes. If n=2, C2 H 6 (ethane); if n=4, C4 H 10 (butane)
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iii) The physical properties of the members change gradually with increase in molecular
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mass. E.g. boiling point, melting point and density increase with increase in molecular mass;
there is a gradual change in state down the group (methane is a gas, pentane is a liquid and
decane is a solid); solubility decreases down the group as molecular mass increases.
iv) Members in each homologous series differ from the next by –CH 2 group (methylene
group).
v) Members have the same general method of preparation
Hydrocarbons
These are compounds consisting of only hydrogen and carbon atoms. They have a general
formula of CxH y where x and y can be any numerical whole numbers.
Hydrocarbons are classified into three main groups as alkanes, alkenes and alkynes.
These three are differentiated by the following functional groups.
Alkanes
These are saturated hydrocarbons with the general formula of CnH 2n+2 . Where n is the
number of carbon atoms. Alkane members are referred to as the paraffin i.e. they have little
affinity to react.
Sources of alkanes
The main sources of alkanes include:
i) Natural gas. This contains mainly methane with small amounts of other gases like propane
and butane. Methane is formed by anaerobic decomposition of organic matter and it is
found in swamps, stagnant ponds and marshes.
ii) Petroleum. This contains a wide range of alkanes ranging from molecular gases to high
molecular waxy solids (C2 -C40 ). Petroleum is formed by anaerobic decomposition of sea
plants and animals. The components of petroleum are separated by fractional distillation, a
process known as refining.
Nomenclature of alkanes
According to IUPAC (International Union of Pure and Applied Chemistry), all members of
alkanes have their names ending with the suffix –ane.
Value of n Formula Name
1 CH 4 Methane
2 C2 H 6 Ethane
3 C3 H 8 Propane
4 C4 H 10 Butane
5 C5 H 12 Pentane
Straight chain alkanes have a prefix n before the normal name e.g.
CH 3 CH 2 CH2CH3 n-butane
In branched
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ONa hydrocarbon or other atoms like chlorine, and
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bromine.
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The hydrocarbon side chains have one hydrogen less the parent alkanes and are generally
referred to as alkyl groups. The alkyl groups derive their names from respective parent
alkanes e.g.-CH 3 (methyl); -CH 2 CH 3 (ethyl); -CH 2CH2 CH 3 (propyl); - CH 2 CH 2 CH2CH3 (butyl).
i) Name the longest unbranched carbon chain .i.e. the longest carbon chain consists of
5-carbon atoms, it is therefore a derivative of pentane
ii) Give the number showing position of the branch. Count from the side that will give
the branch the lowest possible number. E.g. the branch is on the 2nd carbon atom
(the branch replaces hydrogen on the 2nd carbon)
So, write the name of the alkane starting with the carbon position on which the branch is
located (2); put a dash (-); write the name of the branch/substituent group (methyl)
followed by the name of the longest straight carbon chain.
iv) If the branches of side chains are more than one and are similar, di, tri, etc are used.
CH 3 CH 3
2,2-dimethylpentane
3,3-dimethyl hexane
v)If the side chains are different, naming follows alphabetical order
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Note: the longest unbranched chain has 6-C
atoms;it istherefore a derivative of hexane.
3-chloro, 3-methylhexane
Structural formula (graphical formula) shows the arrangement of atoms in one molecule of
a compound.
Alkanes like other hydrocarbons and other organic compounds have covalent bonds
between the atoms. In alkanes, the carbon atoms use all the four outer most electrons to
form covalent bonds by sharing with other carbon atoms and hydrogen atoms. Because all
the electrons are used up in the formation of covalent bonds, they are called saturated
hydrocarbons.
Ethane C2 H 6
Propane C3 H 8
Butane C4 H 10
Isomerism
This is the existence of a compound with the same molecular formula but different
structural formulae.
Isomers are compounds with the same molecular formula but different structural
formulae.
All hydrocarbons with four or more carbon atoms per molecule possess isomers. E.g.
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butane (C4 H 10 )
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2-methyl
propane
n-butane
2-methylpentane
n-hexane
3-methylpentane
2,2 -dimethyl butane
Properties of alkanes
Alkanes are not so reactive and undergo combustion and chlorination reactions only.
1. Combustion
Alkanes undergo complete combustion in plenty of oxygen to form carbon dioxide and
water vapour. For example, methane explodes in air/ oxygen on application of flame
The combustion of alkanes produces considerable amount of heat. This explains why they
are used as fuel for domestic and industrial uses.
The in complete combustion of carbon occurs in cylinders of petrol engines that results in
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to release of poisonous carbon monoxide and sometimes even carbon. It is therefore
dangerous to run a car engine in a garage where there is no free air circulation.
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2. Chlorination
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Alkanes undergo substitution reaction with halogens. A substitution reaction is reaction in
which an atom or a group of atoms in a compound is/are replaced by other atoms.
For the case of alkanes, this is only possible with halogens, e.g. when sunlight shines on a
mixture of methane and chlorine, the chlorine replaces hydrogen in a chain reaction i.e.
substitution reaction occurs as follows:
Refining fuel
The different alkanes that make up petrol can be separated by fractional distillation.
This is based on the boiling points of the different components.
After the removal of impurities mainly sulphur compounds, it is heated until when most of
it vaporizes. The vapour is passed into the bottom of a tall fractionating tower. The
fractionating tower is divided into several compartments each cooler than the one below it.
During fractional distillation, the fraction of petroleum that is most volatile settles at the
top, the non-volatile heavy oil runs out, and the bottom of the column.
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Fractionating tower
Cracking is the breaking down of large complex hydrocarbons into smaller molecules (of
short carbon chain) by use of heat or catalyst. Heavy alkanes are cracked to produce
useful alkenes and fuel of high quality (relatively smaller alkanes). E.g.
C10 H 22 C7 H 16 + C3 H 6
Cracking can be classified in to:
i)
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break them into smaller molecules.
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ii) Catalytic cracking: this involves the use of a catalyst to break down large
andcomplex hydrocarbons in to simpler ones. Catalysts commonly used are silicon
(IV) oxide and aluminium oxide. Catalytic cracking takes place at a relatively low
temperature and pressure.
ALKENES
Alkenes are unsaturated hydrocarbons with a general formula of CnH 2n. where n=2 or more.
They are characterized by possession of a double bond between carbon atoms.
or CH 2 =CHCH3
4 C4 H 8 Butene
or CH 2 =CHCH2CH 3
Isomerism
Isomerism in alkenes begins when n=4i.e from butene. Isomers of butane are:
Ethene
This is the simplest alkene with molecular formula, C2 H 4.
Laboratory preparation
Ethene is prepared by dehydration of ethanol using excess concentrated sulphuric acid.
Set up
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Procedure
- To 50cm3 of ethanol, add 100cm3 of concentrated Sulphuric acid slowly while shaking
under a tap
- The apparatus is set as above and the mixture heated with care to 180˚C. Ethene is
evolved and is collected over water.
NB. The wash bottle of alkali solution removes sulphur dioxide produced in small quantity as
ethanol reduces sulphuric acid slightly. The alkali also removes fumes of the acid.
Ethene can also be prepared by catalytic dehydration of ethanol. Here, ethanol vapour is
passed over a heated catalyst to produce ethane.
Properties of ethene
Physical properties
- Is a colorless gas with a faint sweet smell
- It is insoluble in water but soluble in organic solvents eg benzene and methylbenzene
- It is slightly less dense than air
Chemical properties
Alkenes are generally more reactive than corresponding alkanes. They undergo the
following reactions
a) Combustion
Ethene burns in excess oxygen with a smoky flame since it contains a relatively high
percentage of carbon forming carbon dioxide and water vapour
C2 H4 (g) + 3O2 (g) 2CO2 (g) +2H2 O (g) ( ()
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double bond or triple bond
Examples;
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i)When ethene gas is bubbled through bromine water, bromine water changes from red
brown to colourless i.e. the red brown color of bromine is discharged
When chlorine gas is mixed with ethane and the mixture left in sunlight, the two combine
forming a colorless oily liquid called 1,2-dichloroethane
When the liquid formed above is boiled with water, ethanol is produced
e) Polymerization
Ethene under a very high pressure becomes a liquid. When this liquid is strongly heated to
about 200°C in the presences of a little oxygen catalyst, a white waxy solid (Polyethene) is
obtained.
nCH 2 =CH 2 - CH 2 CH 2 n
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Uses of ethene
- it is used in the manufacture of ethanol
- it is used in the ripening of fruits
- it is used in the manufacture of plastics (synthetic polymers e.g. polythene)
- it is also used in preparing other solvents
Polymerization
Is the combination of many molecules of the same compound with relatively small
molecular masses to form one complex molecule with very large molecular mass.
The complex molecule with a large molecular mass formed by the combination of many
molecules of relatively small molecular masses is called the polymer. The small molecules
from which a polymer is built are called monomers
Types of polymerization
These are mainly two i.e. addition and condensation
Addition polymerization
This is a combination of many small but unsaturated molecules to form a large molecule
without any other product. In this case, the polymer possess the same empirical formula
as the monomer. E.g. in the formation of Polyethene
nCH 2 =CH 2 -(CH2 -CH 2 ) n -
(Monomer-ethene) (Polymer-Polyethene)
Condensation polymerization
In the condensation polymerization, two different molecules combine to form one large
molecule with consequent loss of simple molecules like water, hydrogen chloride etc. so
the empirical formula of the monomer and the polymer are not the same e.g. formation of
starch from glucose and formation nylon 6,6
Types of polymers
Polymers can broadly be divided into two groups namely natural polymers and synthetic
polymers
Natural polymers
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Polymer Monomer Use
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Polyethene ethene -Making containers, eg plastics bowls
and dust bins
-used as wrapping materials
Plastics
A plastic is a substance, which when soft can be formed into different shapes
Plastics are minor products formed by cracking of crude oil eg poly ethene. Polyvinyl
chloride. Melamine
All synthetic polymers are plastics in nature
Advantages of plastics
-They are good thermal and electrical insulators
- They can easily be shaped and molded (they are ductile)
- They resistant to acids and alkalis and they do not rust
-plastics can be coloured when they are being manufactured and they do not need
repainting
- They are light and therefore
portable -They are cheap
Disadvantages
- Produce poisonous fumes when they are burnt
- They are non-biodegradablei.e they do not decay naturally
- Where serious fire hazards occur, molten plastics can inflict very severe burn
Types of plastics
Plastics can be put into two types depending on their behavior upon heating i.e thermo-
softening plastics and thermo-setting plastics
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The long polymer chains in thermoplastics lie alongside each other. They may be entwined
on each other but the polymer chains are not linked (not bonded to each other). When
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heated, the chains slide over each other making them soft and runny.
Examples of thermoplastics
1. Polythene
Polythene is a polymer of ethene. There are two types of polythene i.e. low-
densityPolyethene and high-density polythene.
i) Low density polythene
This is made by polymerizing ethene at a high pressure of 1000-2000 atmospheres and
temperature of 200˚C. Oxygen is used as a catalyst. It has a lower softening temperature
of 105˚C-120˚C. The low density is due to poor packing of the branched polymer chains.
The low-density polythene is soft, light and flexible
Uses:
For making polythene bags; insulation of electric cables because they can withstand bad
weather conditions; making of squeeze bottles such as wash bottles; making plastic bags.
Disadvantage:
At boiling water temperature, they become soft so much that they become flappy and lose
shape.
Uses
For making crates e.g. of beer and sodas, bowls, toys, buckets, food boxes, etc.
PVC are more rigid than Polyethene and are used for making water pipes, light switches
and sockets, insulation for electric cables,, carpets, plastic rain coats etc.
3. Polypropene
This is made by polymerizing propene at a high pressure in the presence of a Ziegler
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catalyst.
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Advantages of synthetic/artificial
polymers
- Relatively low production cost compared to the cost of extracting
natural
- polymers
.
- They are usually stronger and more resistant to corrosive substances like
acids compared to natural polymers.
They can easily be modified depending on the purpose for which the polymer
is required unlike natural polymers, which are hard to modify. As well, their
Disadvantages of synthetic
quality can easily be improved in terms of appearance, strength etc.
polymers
- Many are non-biodegradable causing pollution to the environment.
- When burnt, they produce toxic gases like hydrogen cyanide (from
polypropenenitrile) thus endangering lives of the people working in the
factories.
Alcohols/Alkanols
These are organic compounds with hydroxyl (-OH) group attached to the
hydrocarbon. Alcohols have a general formula of CnH2n+1OH.
Members of the
series
n Molecular formula Structural formula Name
1 Methanol
2 Ethanol
3 Propanol
Fermentatio
n
This is a process in which carbohydrates like starch and sugars are converted
to alcohol by enzymes. The enzymatic break down of glucose yields simple compounds
like ethanol and carbon dioxide. Some heat is as well generated. Fermentation takes
place in the absence of oxygen (anaerobic process).
Preparation from starch
Starch is heated with malt at a temperature of 60˚C. Malt contains an
enzyme diastase, which hydrolyses starch to maltose.