W EEK7/8 ORGANIC CHEMISTRY

Originally, the term organic chemistry applied only to the study of substances of
plants and animals origin i.e substances formed only by living organisms.
Nowadays, many other similar compounds which do not have any connections
with living organisms are also known.

Organic chemistry is now defined as the carbon compounds. Apart from a few
compounds such as the oxides, the trioxocarbonate (IV) and the metallic
carbides, which are conventionally regarded as inorganic, all other carbon
compounds are grouped together in the separate branch of chemistry.

The presence of numerous organic compounds is due to the following properties

of carbon.

(a) The exceptional ability of carbon atoms to catenate i.e to combine with one
another to form straight chains, branched chains or ring compounds
containing many carbon atoms.
(b) The ease with which carbon combines with hydrogen, oxygen, nitrogen and
the halogens
(c) The ability of carbon atoms to form single, double or triple covalent bonds
(d) The bond energy for carbon to carbon single bond is high
C-C = 846; N-N =163; O-O 146; Si- Si =175

STRUCTURE AND VALENCY OF CARBON

Carbon is a non-metal known to people for a long time under the names charcoal,
soot and diamond. Carbon belongs to group 4 on the Periodic table. it is
tetravalent i.e. it has four valence election and they tend to form covalent
compounds.

Carbon exhibits two oxidation states of +2 and +4. The stability of the +2 state
compounds increases and that of the +4 state compounds decreases on going
down the group.

Carbon
2,4 2p
2S 2
 1S2
Carbon has the above electronic configuration; it has only two unpaired electrons
available for bond formation in its valance shell. For carbon to exhibit a valency of
Four (4), at excited state, on of the 2s electrons is “promoted” to occupy the
empty 2pz orbital, creating four unpaired electrons (one S and three P) in its
valence shell as shown below
1S2 2S1 2p1x 2p1y 2p1z

1S2 2S1 2Px 2Py 2Pz

SOURCES OF HYDROCARBON
The natural sources of hydrocarbon are coal, natural gas and petroleum. These
are often known as fossil fuels because they are
- the remains of plants and animals that died millions of years ago, and
- used mainly as fuels, that is burnt to release heat or other forms of energy
Coal is a solid fuel, petroleum is a dark viscous liquid fuel and natural gas is a
gaseous fuel

CLASSIFICATION OF ORGANIC COMPOUNDS

Organic compounds can be classified into aliphatic and aromatic compounds
according to their molecular structures i.e the arrangement of atoms in the
molecules.
(1) Aliphatic Compound
These are composed of carbon chains in acyclic compounds, the carbon
chains are straight or branched. the important families that belong to this
group are the alkancs, alkenes and alkynes

Sometimes, the end carbon atoms of an open aliphatic chain can also join
together to form a closed system or ring as in cyclopropane and cyclohexane.
Such compounds are known as CYCLIC COMPOUNDS.

(2) Aromatic Compound

Aromatic compounds are a special class of compounds whose structures are
based on the structure of benzene, C6H6
Organic (Hydrocarbon)

Aliphatic Aromatic
e.g Benzene
 Acyclic Cyclic (Cycloalkanes e.t.c.)

Alkanes Alkenes Alkynes

e.g e.g e.g
Methane Ethene Ethyne

TERMS IN ORGANIC CEMISTRY

Homologous Series
The numerous organic compounds can be grouped into a comparatively small
number of series or compounds known as HOMOLOGOUS SERIES. The simplest
series of compounds in organic chemistry is the alkanes.

The alkanes are a series of hydrocarbons with a general molecular formula of

cnH2n+2; where n is whole number with a value of one or more.

A homologous series is a family of organic compounds which follows a regular

structural pattern in which each successive member differs in its molecular
formula by a – CH2- group.

Other homologous series include the alkene, C nH2n, the alkanols, CnH2n+1OH and
the carboxylic acids, CnH2n+1COOH
Homologous series have the following common characteristics

(a) General molecular formula – all members share a general molecular

formula e.g CnH2n+2 for alkanes, CnH2n for alkenes etc.

(b) Difference between successive homologous – each successive member

in such a series differs in its molecular formula by the addition of – CH 2-
group and in its relative molecular mass by an increase of 14

(c) Physical properties – The physical properties of members change gradually

as the number of carbon atoms per molecule increases. For example, the
boiling points of alkanes increase down the series as the molecular weights
increase. Similarly, the melting points and densities of the alkanes also
increase while their solubility in water decreases down the series
(d) Chemical properties – members show similar chemical properties. For
examples, the alkanes are fairly unreactive under ordinary conditions. They
burn in air, forming carbon (IV) oxide and water

(e) General methods of preparation – all members can usually be prepared

by using the same general methods

ALKYL GROUPS

Many homologous series can be regarded as being derived from the alkanes by
the substitution of one or more of the hydrogen atoms by other elements or
group. The univalent groups which is formed from an alkane by the loss of a
hydrogen atom is known as the ALKYL GROUP

Alkyl groups have a general formula of C nH2n+1. They are named after the parent
alkanes by replacing the ending –ane by –yl

Alkyl groups are given the general symbol, R. Sometime, R may stand for more
complex groups than just simple alkyl groups

FUNCTIONAL GROUPS

A functional group is an atom, a radical (group of atoms) or a bond common to a

homologous series and which determines the main chemical properties of the
series. Examples are hydroxyl group, -OH; amino group, -NH 2, Carboxyl group, -
COOH, -ane,-ene

When two or more functional groups occur in one molecule, the properties of one
are often modified or influenced by the presence of the other.

The functional group determines the basic chemistry of a compound while the
alkyl group affects the physical properties of a compound.

SATURATED AND UNSATURATED COMPOUNDS

If an organic compound contains atoms joined only by single covalent bonds, the
compound is said to be saturated. The alkanes are said to be saturated
hydrocarbon. For example
 H H H H H

H–C -C–H and H–C–C–C–

H H H H H

ethane propane

If an organic compound contains carbon atoms joined by double or triple covalent

bonds, the compound is said to be unsaturated. Examples are ethene and ethyne

H H

C=C and H C C-H

H H

FORMULAE OF ORGANIC COMPOUNDS

Empirical Formula: This is the simplest formula of a compound. It indicates the

relative number of each kind of atom in a molecule of a substance. It is found by
determining the percentage composition of the substance by quantitative
analysis.

Molecular Formula: This indicates the actual numbers of each kind of atoms in
a molecule of a substance. The molecular formula is deduced from the relative
molecular mass of the substance and its empirical formula

Structural Formula: In organic chemistry, it is possible that a molecular formula

may represent more than one substance. A more informative formula called the
structural formula is often used to represent a particular organic substance. Such
a formula indicates how the atoms are arranged within the molecule of a
substance

For example, the structural formula of ethanoic acid can be represented as shown
below

H O

H C C
 H O H

but can also be written in a condensed form such as CH 3COOH. This form is
usually preferred because it indicates clearly the functional groups present in the
substance.

The structural formula is usually shown as planar for convenience and does not
imply a flat molecule

ISOMERISM

Isomerism is the existence of two or more compounds (known as isomers) with

the same molecular formula but different molecular structures.

As the number of carbon atoms in a molecule increases, the number of isomers

also increases. For example, pentane has Three possible isomers

H H H H H H H H H

H–C–C–C–C–C–H H–C–C–C–C–H

H H H H H H H H H

-C–

CH3(CH2)3CH3 H CH3CH2CH(CH3)CH3

n – pentane H–C–H 2 – methylbutane

H H

H–C C C–H

H H

H–C–H

C(CH3)4

2,2 – dimethyl propane

Furthermore, it is also possible to have isomers with the same molecular formula
but belonging to different homologous series. For example, both ethanol and
methoxymethane (dimethyl ether) have the molecular formula of C 2H6O but
belong to the alkanol and ether series respectively with different physical and
chemical properties because of their different structural formulae and functional
groups respectively.

Ethanol is a liquid at room temperature and it reacts readily with phosphorus (V)
chloride due to the presence of the hydroxyl group, -OH.

Methoxymethane, which has a lower boiling point, exists as a vapour at room

temperature and does not react with PCl 5 due to the absence of the hydroxyl
group

H H H H

H- C–C–O–H H–C–O–C–H

H H H H

CH3CH2OH CH3OCH2

Ethanol Methoxymethane

GEOMETRIC ISOMERISM

Geometric Isomerism is the existence of compounds with the same molecular

formula but are not identical because of different spatial arrangement of the
compound atoms.

In single bond, butane for instance, only one form of butane exists because there
is free rotation about the C – C single bond. The situation differs if double bonds
are present in which free rotation is hindered by the double bond.

Geometric Isomerism is common among alkenes where each carbon atom joined
by a double bond is attached to two different atoms or groups can exist in the Cis
and trans form CH3 CH3 CH3 H

C=C C=C

H H H H
 Cis – but – 2 – ene trans – but – 2 – ene
Cl Cl H Cl
C=C and C=C
H H Cl H
Cis – 1, 2 – dichloroethene trans – 1, 2 - dichloroethene

OPTICAL ISOMERISM

Optical Isomerism is The existence of two or more compounds with the same
molecular formula but with different configurations

For a compound to be optically active; it must have a carbon atom which is

substituted by four

different groups e.g lactic acid

H H

CH3 - C - COOH HOOC – C - H3C

OH HO

Minor

Lactic Acid

WEEK 9
ALKANES

The alkanes are aliphatic hydrocarbons. They form a homologous series of

saturated hydrocarbons, which can be represented by the general molecular
formula, CnH2n+2

In each alkane member, all the carbon atoms are tetrahedrally bonded to the
hydrogen and other carbon atoms.

Some members of alkane group are Methane, Ethane, propane, Butane, Pentane,
Hexane etc
 METHANE

Methane is the first member and the simplest compound in the Alkane series with
the molecular formula of CH4 .Besides being a component of petroleum gas, it is a
major constituent of natural gas which issues from the ground in great quantities
in certain parts of the world

Methane is produced during the decomposition of plant matter in the absence of

air. It is given off from swamps and is often known as marsh gas

Methane is also found in poorly ventilated coal mines as the dreaded fire damp,
which is the main cause of explosions in these mines

LABORATORY PREPARATION

Methane is usually prepared by heating anhydrous sodium ethanoate with an

alkali, usually soda – lime. Soda lime is quick-lime slaked with a concentrated
solution of sodium hydroxide

It is used in preference to caustic soda because it is not deliquescent and does

not attack glass so readily

Anhydrous sodium ethanoate is ground with an equal mass of soda – lime and
then heated in a hard glass test – tube. Methane is given off and can be collected
over water.

CH3COONa(s) + NaOH(s) Na2CO3(s) + CH4(g)

From soda-lime

(2) Action of Water on Aluminum Carbide

Al4C3(s) + 12H2O(c) 4Al(OH)3(s) + 3CH4(g)

PHYSICAL PROPERTIES
1. Methane is a colourless and odourless gas
2. It is only slightly soluble in water
3. It is less dense than air
4. It has no action on litmus

CHEMICAL PROPERTIES
Combustion

The general equation for combustion of alkanes can be represented as follows

CxHy + (x + y/4) O2(g) y/4 H2O(g) + xCO2(g)

Methane, for example, burns in air or oxygen with a pale non-luminous flame to
produce steam, Carbon (IV) oxide and a lot of heat

CH4(g) + 2O2(g) 2H2O(g) + CO2(g)

Chlorination

Methane reacts with chlorine in the presence of ultra-violet light (which acts as a
catalyst) to yield a mixture of products. These products are formed by the
successive replacement or displacement of the hydrogen atoms in the methane
molecule by the chlorine atoms. This process is called SUBSTITUTION REACTION

The hydrogen is not released as free hydrogen but in combination with chlorine
as hydrogen chloride. The steps of the chlorination are as follow

CH4(g) + Cl2(g) HCl(g) + CH3Cl(g) (chloromethane)

CH3Cl(g) + Cl2(g) HCl(g) + CH2Cl2(g) (dichloromethane)

CH2Cl2(g) + Cl2(g) HCl(g) + CHCl3(g) (trichloromethane)

CHCl3(g) + Cl2(g) HCl(g) + CCl4(g) (tetrachloromethane)

This type of reaction is called SUBSTITUTION REACTION and is a characteristic of

all saturated compounds

USES

1. Methane is mainly used as a fuel, either by itself or mixed with other gases
2. It is used for making hydrogen, Carbon black, Carbon (IV) sulphide, alkynes
3. It is used for making
- tri chloromethane (chloroform); an anesthetic used in surgical operations
- tetra chloromethane (carbon tetrachloride); an important organic solvent

ASSIGNMENT

Draw a well labelled diagram for the Laboratory preparation of Methane

WEEK :10
ALKENES

The alkenes are a homologous series with a general molecular formula of C nH2n,
where n is a positive whole number which is equal to or greater than 2.

Alkenes contain two hydrogen atoms less than the alkanes. This is because,
unlike the alkanes which are saturated compounds, the alkenes are unsaturated
compounds which contain a carbon-carbon double bond in their molecular
structures.

Ethene, propene, but-1-ene and but-2-ene are colourless gases at ordinary

temperatures and pressures, the next Thirteen members of the series are liquids
while the higher members are solids
Alkenes tend to burn with a more luminous and smoky flame than the
corresponding alkanes, since they contain a greater percentage of carbon. The
availability of electrons in the double bonds also makes them chemically more
reactive than the alkanes

Examples are
Molecular formulae Structural formula LUPAC name Common name

C2H4 CH2 = CH2 Ethene Ethylene

C3H6 CH2 = CHCH3 Propane Propylene

C4H8 CH2 = CHCH2CH3 But-1-ene 1-Butylene

C4H8 CH3CH = CHCH3 But-2-ene 2-BUtylene

C5H10 CH2 = CH(CH2)2CH3 Pent-1-ene Pentylene

ETHENE

Ethene is the most important alkene. It is one of the main products obtained
during the cracking of the gas oil fraction of petroleum

LABORATORY PREPARATION

Ethene is prepared by heating ethanol with excess concentrated tetraoxosulphate

(VI) acid at 170oC. The reaction occurs in two stages. On mixing the ethanol and
the acid in a volume ratio of 1:2 respectively, the ester, ethylhydrogen
tetraoxosulphate (VI), is formed

C2H5OH(aq) + H2SO4(aq) C2H5HSO4(g) + H2O(c)

On heating, the ethyl hydrogen tetraoxosulphate (VI) decomposes in the

presence of excess tetraoxosulphate (VI) acid to produce ethene

C2H5HSO4(aq) C2H4(g) + H2SO4(aq)

The overall reaction can be regarded as a dehydration of ethanol by hot

concentrated tetraoxosulphate (VI) acid because the overall change is the
removal of one molecule of water from ethanol

C2H5OH(aq) Con.c H2SO4

C2H4(g)
-H O
2
PHYSICAL PROPERTIES

1. Ethene is a colourless gas with a faint sweetish smell

2. It is only sparingly soluble in water
3. It is slightly less dense than air
4. It has no action on litmus
5.

CHEMICAL PROPERTIES

Combustion

Ethene burns readily in air or oxygen with a smoky and luminous flame because
of its high proportion by mass of carbon. It oxidizes completely to form water and
carbon (IV) oxide

C2H4(g) + 3O2(g) 2H2O(c) + 2CO2(g)

Addition Reaction

Ethene undergoes addition reactions with hydrogen, halogens, hydrogen halides

and many other compounds. Addition reactions are characteristic of all
unsaturated compounds

(a) With hydrogen – if a mixture of hydrogen and ethene is passed over a

finely divided nickel, platinum or palladium catalyst, ethane is formed as an
addition compound
H2C = CH2(g) + H2(g) CH3CH3 or C2H6

This reaction, which is also known as HYDROGENATION, is very important in the

hardening of oils

(b) With the halogens – Chlorine and bromine add on to ethene readily at
room temperature to form the halogenated products 1, 2 – dichloroethene
and 1, 2 – dibromoethene respectively
CH2 = CH2(g) + Cl2(g) CH2ClCH2Cl or C2H4Cl2(c)
CH2 = CH2(g) + Br2(c) CH2BrCH2Br or C2H4Br2(c)

Similarly, with iodine solution (iodine dissolved in ethanol), 1,2–diiodoethene

is formed at room temperature
(c) With chlorine and bromine water – chlorine water, which contains
oxochlorate (I) acid, HOCl, combines with ethene to give 2-chloroethanol
H H
C=C + HOCl(aq)
H H(g)

H H

H C C H 2-chloroethenol

HO Cl

or CH2OHCH2Cl(aq)

(d) With tetraoxosulphate(VI) acid – H2SO4 readily absorbs ethene at room

temperature to form ethyl hydrogentetraoxosulphate (VI)

H H

C=C + H2SO4(aq)

H H(g)

H H

H- C - C - H- + H2O(ag) H – C – C – H + H2SO4(ag)

OSO2OH H OH
ethanol

(e) With tetraoxomanganate(VII) – When bubbled through a dilute solution of

potassium tetraoxomanganate (VII) , ethene is oxidized rapidly to ethane – 1,
2 – diol (ethylene glycol)

CH2 = CH2(g) + H2O(l) + (O) CH2OHCH2OH(aq)

from tetraoxo
manganate(VII)
In the process, the purple potassium tetraoxomanganate(VII) solution is reduced to
- a green solution of potassium tetraoxomanganate (VI) if the solution is
alkaline, or
- a colourless solution of a manganese (II) salt if the solution is acidic.

POLYMERIZATION
This is a process whereby Two or more simple molecules are linked to form a
much larger molecule. Ethene and its derivatives undergo polymerization to form
important compounds such as poly(ethene) and poly (chloroethene)

2nCH2 = CH2 (CH2 – CH2 – CH2 – CH2) (Polymerisation)

Ethene pressure + Polyethene
catalyst

SPACE FOR DIAGRAM

USES

(1) Ethene is the main source of many important organic compounds such as
ethane, ethanol, ethanoic acid, epoxyethane, ethane – 1, 2 – diol, tetraethyl
lead (IV).
(2) Ethene is the raw material used for making many important plastics such as
– Poly (ethene)
 – Poly (chloroethene), also known as polyvinyl chloride (PVC)
(3) It is used to produce synthetic rubber such as styrene – butadiene rubber
(SBR), Thiokol.
(4) A derivative of ethene, 1,2 – dibromoethene is used as a petrol additive.
(5) In agriculture, low concentrations of ethene are used to hasten the ripening
of fruits.

ASSIGNMENT

List five (5) plastic products made from ethene.

Draw diagram for the laboratory preparation of Alkenes in the space provided
above

WEEK 11
ALKYNES
Alkynes are the homologous series of unsaturated hydrocarbons with a general
molecular formula of CnH2n-2 where n is a positive whole number which is equal to
or greater than 2.
Alkyne molecule contains a carbon-carbon triple bond (- C C -) by the sharing of
Three pairs of elections. The names of all the alkynes end with –yne. Examples of
alkyne members are
Molecular formula structural formula IUPAC name
C2H2 CH CH Ethyne
C3H4 CH CCH3 Propyne
C4H6 CH CCH2CH3 But-l-yne
C4H6 CH3C CCH3 But-2-yne
C5H8 CH C(CH2)2 CH3 Pent-1-yne

EHTYNE
Ethyne is the first member of the alkyne series. It has a molecular formula C 2H2
and a structural formula, CH CH

PREPARATION
Ethyne is usually prepared in the laboratory by the action of cold water on
calcium carbide. The gas evolved is first through an acidified copper (II) tetra
oxosulphate (VI) solution to remove any passed PH 3, present as an impurity and
then collected over water. The process is accompanied by the released of a large
amount of heat so the reaction is performed on a heap of sand inside the flask to
prevent the latter from cracking
CaC2(s) + 2H2O(c) Ca(OH)2(aq) + C2 H2(g)

PHYSICAL PROPERTIES
1. Ethyne is a colourless gas with a characteristic sweet smell when pure
2. It is only sparingly soluble in water
3. It is slightly less dense than air
4. It is unstable and may explode4 on compression to a liquid. For storage
purposes, it is usually dissolved in prop none (acetone) and kept in steel
cylinders at about 12Atm pressure

CHEMICAL PROPERTIES
Combustion
Ethyne burns in air to give a very smoky and luminous flame due to high carbon
content.
2C2H2(g) + 5O2(g) 2H2O(g) + 4 CO2(g)

Addition Reactions
(a) With hydrogen Ethyne reacts with hydrogen in the presence of nickel
catalyst at about 200 C to form first ethene and then ethane
o

+H2 H H +H2 H H
H–C C–H C =C H–C–C–H
H H H H

(b)With the halogens reacts with chlorine & bromine in the presence of a
metallic halide catalyst at room temperature to yield halogenated compounds
+Cl2
H–C C–H Cl – C = C – Cl
1,2 - dichloroethene

+Cl2 Cl Cl
Cl – C = C – Cl
Cl Cl
1,1, 2,2-tetra chloroethane
(c) With Water - If ethyne is passed through dilute H 2SO4 acid, at about 60oC,
with Mercury (II) tetra oxosulohate (VI) as a catalust, addition of water takes
place as shown forming ethanol
+H2O
H–C C–H H–C=C–H
ethyne H OH ethanol
Br2 Br
H–C–C–H
H O 2-bromoethanal
Ethenol & ethanol are isomers

SUBSTITUTION REACTION
If ethyne is passed through ammoniacal solutions of copper (I) chloride and silver
trioxonitrate (V) at room temperature, precipitates of copper (I) dicarbide (reddish
brown) and silver dicarbide (whitish yellow) will be formed respectively

C2H2 (g) + 2CuCl(aq) Cu2C2(g) + 2HCl(aq)

C2H2 (g) + 2AgNO3(aq) Ag2C2(s) + 2HNO3(aq)

Both the dicarbides are explosive when dry and both give ethyne if warmed with
a dilute acid. These reactions distinguish ethyne from ethane which does not
form these metallic derivatives.
Cu2C2(s) + H2SO4(aq) Cu2SO4(aq) + C2H2(g)

POLYMERIZATION
Ethyne polymerizes to form the aromatic hydrocarbon, benzene, when it is
passed through a hot tube containing a complex organo-nickel catalyst
3C2H2(g) C6H6(l)

TEST FOR UNSATURATION

Unsaturated compounds are best recognized by their addition reactions. The
most convenient test is the reaction with bromine or bromine water (reddish-
brown) since these reagents become colourless on reacting with unsaturated
compounds.

USES
1. Ethyne is sometimes used as fuel in lamps such as miners’ lamps. The ethyne
lamp can be very bright if there is a sufficient supply of air
2. Ethyne is mixed with oxygen to produce a very hot and easily controllable
flame, known as the oxy-ethyne flame, which is used for cutting and welding
metals
3. Ethyne is a source of ethanal and the solvents, 1,1,2-trichloroethene and
1,1,2,2-tetrachloroethane, which are extensively used in industry and in dry
cleaning for dissolving grease
4. Polymerization of ethyne and its derivatives leads to the synthesis of products
such as
- Poly (chloroethene), a plastic
- Poly (propenonitrile), a synthetic fibre, and
- Neoprene, an artificial rubber

ASSIGNMENT
1. Distinguish between the followings
(a) Ethyne and Ethane
(b)Alkenes and Alkynes
2. Give the IUPAC names of the following organic compounds
(a) CH3Cl (b) C2H4Cl2 (c) CCl4 (d)C3H7I
Write the formulae of the following organic compounds
(a) 2-methyl-2-hydroxyl propane
(b)3-methypentene

BENZENE
Aromatic compounds are benzene and compounds that resemble benzene in
chemical behaviour. Benzene is obtained from the destructive distillation of coal.
It is also produced naphtha which is obtained from one of the light petroleum
fractions

STRUCTURE
The structure of benzene remained a mystery until 1865 when August kekule
proposed his structure for benzene. He suggested that since the molecular
formula of benzene was found to be C 6H6, the most logical structure would be for
the six carbon atoms to form a ring as represented below

H
C
H C C H
 H C C H
C
H

According to kekule there should be three alternate carbon-carbon double bonds

in the benzene are found to be equal and intermediate in length
H
C C
C C H C C H
C C H C C H
C C
H

In 1945, the concept of resonance was used to explain the structure of benzene.
Resonance occurs when two equivalent forms of a compound are in equilibrium.
The real structure of benzene is represented as a hexagon with a ring in it,
indicating that the double bonds are shifting at all times.

Some common aromatic compounds are phenol, toluene and xylene. These
compounds are obtained by substituting the hydrogen atoms in the benzene ring
with the appropriate atom(s) or group(s)

OH CH3 CH3

CH3

Phenol toluene xylene

PHYSICAL PROPERTIES
1. Benzene is a colourless liquid with a sweet smell
2. It is insoluble in water
3. It has a boiling point of 80oC

CHEMICAL PROPERTIES
Benzene undergoes substitution reactions e.g chlorobenzene is formed when
benzene reacts with chlorine
Cl
Fe
(l) + Cl 2(g) (l) + HCl(g)
FeCl3

Benzene also undergoes addition reactions e.g cyclohexane is formed when a

mixture of benzene vapour and hydrogen are passed over nickel catalyst nat
180oC
H2
C
Ni H2C CH2
(l)+ 3H2(g) 180 C
o

H2C CH2 (g)

C

H2
Cyclohexane

USES
1. Benzene can be converted to styrene which is used in the manufacture of
synthetic fibres like nylon
2. Benzene is an important source of phenols, aniline and chemicals which are
used as pesticides and detergents
3. Many derivatives of benzene are useful
- Toluene is used in making explosives
- Phenol is used as a disinfectant and as a raw material for making plastics
- Aniline and aniline-type compounds are used for making dyes and drugs
WEEK 12
ALKANOLS
Aliphatic alkanols are compounds in which hydroxyl groups are linked to alkyl
groups. They can be considered as being derived from the corresponding alkanes
by replacing the hydrogen atoms with hydroxyl groups. This group is the
functional group of the alkanols as it is responsible for their characteristic
chemical properties. The monohydric alkanols form a homologous series with the
general molecular formula CnH2n+1OH (or CnH2n+2O)

The simplest member of the series is methanol, CH 3OH, sometimes known as

wood spirit, because it was produced by the destructive distillation of wood in the
early days. It is poisonous and can cause blindness
The IUPAC name of the First few members of alkanols are
Molecular formula Structural formula IUPAC
name
CH4O CH3OH Methanol
C2H6O CH3CH2OH Ethanol
C3H8O CH3(CH2)2OH Propan-1-ol
C3H8O CH3CHOHCH3 Propan-2-ol
C4H10O CH3(CH2)3OH Butan-1-ol

TYPES OF ALCOHOLS
Primary Alcohol – this has only one alkyl group attached to the carbon atom
that carries the hydroxyl group.

Secondary Alcohol – has two alkyl groups attached to the carbon atom that
carries the hydroxyl group

Tertiary Alcohol – Has three alkyl groups

1o H CH3 H

R C OH H2C C C OH

H H H

2-methylpropan-l-ol

2o R CH3

R C OH H5C2 C OH

H H2

Butan-2-ol

3o R’ CH3

R C OH H3C C OH

R’’ CH3

2-methylpropan-2-ol
Examples of polyhydric alkanols are ethane 1, 2-diol (ethylene glycol) which is a
dihydric alkanol and propane. 1,2,3-triol (glycerol) which is a trihydric alkanol

ETHANOL

Ethanol has the molecular formula C2H5OH and the structure of

H H

H C C OH

H H

It is a very important compound because it has more uses than almost any other
organic compound. It is the essential ingredient in alcoholic drinks and is well
known for its intoxicating effect on consumers

PREPARATION

Ethanol can be prepared in the laboratory by several methods e.g

- Hydrolyzing iodoethane with an alkalis
- Hydrolyzing ethyl esters with a hot alkali
- Reducing ethanol with nascent hydrogen
Commercially, ethanol is usually prepared from
- Ethene and
- By fermentation

From Ethene

Ethene is obtained in large quantities by the cracking of petroleum. It is first

absorbed in 95% tetraoxosulphate (VI) acid at 80oC and 30 Atm to form ethyl
hydrogen tetraoxosulphate (VI). This is then hydrolyzed by boiling with water

C2H4(g) + H2SO4(aq) C2H5HSO4(aq)

C2H5HSO4(aq) + H2O(c) C2H5OH(aq) + H2SO4(aq)

The ethanol formed is distilled off, leaving the acid which can concentrated and
used again

By Fermentation
Fermentation is the slow decomposition by micro-organisms of large organic
molecules (such as starch) into smaller molecules (such as ethanol)

Starchy foodstuff like potatoes and cereals are the main source of ethanol in
many countries. The starch granules are first extracted by crushing and pressure
cooking the material. They are then treated with malt at 50 oC to 60oC for an hour.
Malt is partially germinated barley, which contains the enzyme diastase. The
starch is converted by this enzyme into maltose
2(C6H10O5)n(s) + nH2O(c) diastase 2C12H22O11(aq)
Starch

Yeast is then added at room temperature. Yeast contains two enzymes, namely
maltase which converts the maltase to glucose and zymase which then
decomposes the glucose into ethanol and carbon (IV) oxide
C12H22O11(aq) Maltase 2C6H12O6(aq)
Maltase Glucose

C6H12O6(aq) Zymase
2C2H5OH(aq) + 2CO2(g)
glucose ethanol

PHYSICAL PROPERTIES
1. Ethanol is a colourless volatile liquid with a characteristic taste and smell
2. It is readily soluble in water in all proportions (due to the presence of the
hydroxyl groups)
3. It has a boiling point of 78oC
4. It has no action on litmus

CHEMICAL PROPERTIES
Combustion
Ethanol readily burns in air or oxygen with a pale blue flame, yielding water and
carbon (IV) oxide
C2H5OH(aq) + 3O2(g) 3H2O(c) +2CO2(g)

Reaction with Sodium and Potassium

Metallic sodium added to come ethanol at room temp hydrogen gas is liberated
2C2H5OH(aq) + 2Na(s) 2C2H5ONa(aq) + H2(g)
` ethanol sodium ethoxide

Sodium ethoxide (white deliquescent solid) is rapidly hydrolysed by cold water,

giving an alkaline solution
C2H5ONa(g) + H2O(l) C2H5OH(aq) + NaOH(aq)

Reactions with The Chlorides To Phosphorus

Ethanol reacts vigorously with phosphorus(V) chloride in the cold, liberating
steamy fumes of hydrogen chloride and chloroethane vapour
C2H5OH(aq) + PCl5(s) C2H5Cl(g) + POCl3(c) + HCl(g)
Phosphorus (III) chloride gives similar but less vigorous reaction
3C2H5OH(aq) + PCL3(l) 3C2H5Cl(g) + H3PO4(aq)

Oxidation

Ethanol is readily oxidized to ethanal by warming with potassium

heptaoxodichromate (VI) solution which is acidified with dilute H 2SO4
C2H5OH(aq) [0] CH3CHO(g) + H2O(l)
from pota hepto

On further oxidation in the presence of excess H 2SO4, the ethanol is converted to

ethanoic acid

CH3 CHO(g) [o]

CH3COOH(aq)

Note

Wine sometimes becomes sour on prolonged exposure to air because of the

bacterial oxidation of ethanol to ethanoic acid.

Esterification

Ethanol reacts reversibly with acids forming ethyl esters. This process is known as
esterification. For example, ethanol and ethanoic acid react to give ethyl
ethanoate

CH3COOH(aq) + C2H5OH(aq) CH3COOC2H5(c) + H2O(l)

ethanoic acid ethyl ethanoate

USES
1. Ethanol is used to dissolve resins, varnishes, larquer, soaps, perfumes, dyes,
drugs and flavouring extracts.
2. It is the raw material in the manufacture of many important compounds e.g
ethanal, ethylester, halides, ethoxyethane and trichloro ethanal
3. It is used as fuel, either by itself or mixed with petrol, in racing car and in
rockets
4. It is sometimes used as an antifreeze in anti mobile radiators
5. Ethanol is present in many alcoholic beverages such as beers, wines and
spirits (e.g whisky, gin, brandy, rum etc)