SS3 FIRST TERM NOTE INTRODUCTION

Organic chemistry is the study of compounds of carbon occurring naturally excluding oxides and
trioxocarbonate (IV) which have inorganic origin. Today we have over two million known organic
compounds. Many are yet to be discovered.
UNIQUENESS OF CARBON
1. Carbon forms single, double or triple bonds between its own atoms. This is known as
CATENATION. i.e. C-C, C=C, C≡C.
2. It uses 4-valence electrons to form covalent bonds with Halogens, Nitrogen, sulphur and
oxygen and ionic bonds between a number of metals.
3. Atoms within a molecule can be rearranged in two or more different forms. This is called
ISOMERISM. And the different forms are ISOMERS
4. It can form a continuous chain, branched or rings. Infect, the number of carbon atoms in a
molecule of organic compound ranges from one as in methane to over 1000 atoms that are
covalently continuously bonded as in polymer. Generally, carbon is the most important element
in the study of organic chemistry.
NATURAL SOURCES OF ORGANIC COMPOUNDS
In plants- Carbohydrates, Vegetable oil etc.
In animals- Oils, fats, protein etc.
In minerals- Crude oil and coal.
In fungi and micro-organism- Enzymes.
IMPORTANCE OF ORGANIC CHEMISTRY
It helps us to know how organic compounds are developed and manufactured as our daily needs-
soap, tooth paste and brush, plastic, kerosene, candle sticks, insecticides.
Household materials: Chairs, table spoons, carpets, mattresses, pillows and rugs.
Clothing materials: Man made (artificial textiles, fibers, polyesters, nylon silk, nylon, dyes, buttons
etc.
Drugs: Panadol, Aspirin, Cough Syrup and blood tonic and capsule.
 CLASSIFICATION OF ORGANIC COMPOUNDS
ORGANIC COMPOUNDS

Hydrocarbon Non- Hydrocarbon

Aliphatic Aromatic Acidic Basic Neutral

Open Branch Cyclic

Hydrocarbons are organic compounds containing Hydrogen and Carbon only.

ALIPHATIC HYDROCARBONS: These are hydrocarbons that have open chains, branched
chains or cyclic chains.
AROMATIC HYDROCARBONS: These are hydrocarbons that have Benzene ring as its basis.
That is, they are benzene derivatives e.g. Benzenol (phenol), methyl benzenol (Toluene), Amide
Benzenol (Anilene).
NON- HYDROCARBONS: These are derived from hydrocarbons by replacing one of the
Hydrogen atoms with halogens (F, Cl, Br, I) or Heteroatoms: -CN, -OH, -COOH, -NH2.
HOMOLOGOUS SERIES AND FUNCTIONAL GROUPS
A family of organic compounds with the same functional group is termed homologous series.
Functional groups: This is a covalent bond or heteroatoms that is common to a group of organic
molecules which determines their physical and chemical properties (of the molecules/ organic
compounds).
CHARACTERISTICS OF HOMOLOGOUS SERIES
i. They conform to a general chemical formula
ii. They differ from one another by constant -CH2 or 14 atomic mass.
iii. They have the same method of preparation
iv. They contain the same functional group
v. There is a gradual change from one physical state to another. E.g. boiling point, melting point,
density and viscosity as the relative molecular mass increases. vi. They have similar
chemical and physical properties. E.g. solubility.
 MAJOR HOMOLOGUES SERIES

Exercise
i. What will be the formula of the third member of the alkane if the formula of the second? ii.
What will be the relative molecular mass of the second number if the first member is 16? iii.
Find the value of x and y in the following alkanes – CxH12, C4Hy.
 ALKANES
Alkanes are hydrocarbons which conform to a general chemical formula CnH2n+2 where n is a
positive integer starting from 1. It is otherwise called paraffins. It has in each molecule carbon to
carbon (C-C) single bonds, hence it is said to be saturated.
N Name Formula Structure Structural
formula
1 METHANE CH4 H CH4
H-C-H
H
2 ETHANE C 2 H6 HH CH3CH3
H-C-C-H
HH
3 PROPANE C3H8 HH H CH3CH2CH3
H-C-C-C-H
HH H

4 BUTANE C4H10 HH HH CH3(CH2)2CH3

H-C-C-C-C-H
HH HH

5 PENTANE C5H12 HH HHH CH3(CH2)3CH3

H-C-C-C-C-C-H
HH HHH

6 HEXANE C6H14 HH HHHH CH3(CH2)4CH3

H-C-C-C-C-C-C-H
HH HHHH

7 HEPTANE C7H16 HH HHHHH CH3(CH2)5CH3

H-C-C-C-C-C-C-C-H
HH HHHHH

8 OCTANE C8H18 HH HHHHHH CH3(CH2)6CH3

H-C-C-C-C-C-C-C-C-H
HH HHHHHH

9 NONANE C9H20 HH HHHHHHH CH3(CH2)7CH3

H-C-C-C-C-C-C-C-C-C-H
HH HHHHHHH
 10 DECANE C10H22 CH3(CH2)8CH3
HH HHHHHHHH
H-C-C-C-C-C-C-C-C-C-C-H
HH HHHHHHHH

GENERAL PHYSICAL PROPERTIES OF ALKANES

1. i. C1-C4 – Colourless, odourless gases ii. C5-C16 – Colorless
liquids (oil) iii. C17- above – Waxy solids
2. Boiling point, melting point and density increases with increase in
molar mass. The reason being that the Vander Waal’s attraction
force between each molecule
PREPARATION OF ALKANES- METHANES
Methane is prepared in the laboratory by the addition of sodium hydroxide (NaOH) to aqueous
solution of sodium ethanoate CH3COOH with little amount of calcium hydroxide to avoid/ prevent
damaging the apparatus. See the equation for reaction below:

CH3COONa(aq) + NaOH(aq) → CH4(g) + Na2CO3(aq)

Sodium ethanoate Sodium hydroxide Methane Sodium trioxocarbonate (IV)
The gas is collected by upward delivery or downward displacement of air because it is lighter than
air. It is a colourless, odourless gas insoluble in water and burns in oxygen with blue flame. It has
no effect on litmus papers, bromine water and potassium tetraoxomanganate (VII) solution because
it is saturated.

RCOONa + NaOH → Na2CO3 +RH

REACTIONS OF METHANE (ALKANES)

 Methane undergoes the following reaction:
1. Burning in the presence of oxygen (combination reaction)

CH4(g) + 2O2(g) → CO2(g) + 2H2O(g) (Pale blue flame)

The products are carbon (iv) oxide and water
The general formula for balancing combustion reaction involves any member of the alkane
homologues: -

CxHy + (𝑥+ 𝑦)O2 → xCO2 + 𝑦 H2O

4 2

(N/B) Insufficient O2 produces lampblack and carbon II oxide.

Exercise
Using the above formula, balance the following equations

C5H12(g) + O2(g) → CO2(g) + 2H2O(g) (x=5, y=12)

C3H6(g) + 2O2(g) → CO2(g) + 2H2O(g) (x=3, y=6)

USES OF METHANE
i. It is used for heating the blast furnace
ii. It is used in producing Carbonblack.
2. Substitution reactions with halogens-(x)
Alkanes can only undergo substitution reaction with any member of the halogens to yield
Halogenated alkane and Hydrogen Halides.
𝑢𝑣
CH4 + Cl2 → CH3Cl + HCl (Methane monochloride)
𝑢𝑣
CH3Cl + Cl2 → CH2Cl2 + HCl (Methane dichloride)
𝑢𝑣
CH2Cl2 + Cl2 → CHCl3+ HCl (Methane trichloride)
𝑢𝑣
CHCl3 + Cl2 → CCl4(g) + HCl (Methane tetrachloride)
𝑢𝑣
Net equation CH4 + 4Cl2 → CCl4(g) + 4HCl
Can also be called Carbon tetrachloride – It is used as an organic solvent e.g. paper liquid.
USES OF ALKANES
i. It is used as fuel C1= -390KJ, C2= -1555KJ, C3= -2215KJ
ii. It is used for producing lampblack, typist ink, pigments in black paint, cooking gas,
production of ethene by a process called cracking.
 ALKENE (OLEFFINS)
This is another hydrocarbon with carbon to carbon double bonds C=C. the double bond can be
more than one in a molecule i.e. diene, triene etc. the double bond makes Alkenes unsaturated.
General chemical formula is CnH2n – where n=2,3,4,5… The naming of each member is done by
replacing the a in alkane with e as in ethene derived from ethane. However, the position of the
double bond is always indicated – making use of the smallest possible number. This applies to
alkenes that have at least 4 carbon atoms in the longest chain. Examples

a b

a
and b are called butene. But you can discover that the double bond is not in the same position in
each case. Thus, “a” is but-2-ene while “b” is but-1-ene.
n NAME FORMULA STRUCTURE
2 Ethene C2H4 H–C=C–H
H H
3 Propene C3H6 H HC=
C–C–H H
H H
4 Butene C4H8 H H
H–C–C=C–C–H
H H H H
5 Pentene C5H10 H H H H H
H–C–C–C–C=C
H H H H H
6 Hexene C6H12 H H H H
H–C–C–C–C–C=C–H
H H H H H H
7 Heptene C7H14
8 Octene C8H16
9 Nonene C9H18
10 Decene C10H20
NOMENCLATURE/ISOMERISM IN ALKENE H HH–C–C=C–C–H
H Cl Cl H
This is but-2-ene, because of the chlorine atoms attached. Therefore, the IUPAC name for the
structure is 2,3-dichloro-but-2-ene.
Note the longest chain, the position of the double bond was indicated last while the substituent
atoms and their positions indicated if there are more than one substituent atom from different
elements, those elements are arranged in alphabetical order. Br, Cl, F, and I.
GEOMETRIC ISOMERS

CIS but-2-ene Trans- but-2-ene

For Cis – the same substitutes are on the same side of the double bond.
For Trans – the same substitutes are on the opposite side of the double bond.
PREPARATIONS OF ALKENES
1. Dehydration of alkanols
Alkenes are prepared in the laboratory by dehydrating saturated alkanol using excess concentrated
tetraoxosulphate (VI) acid. Dehydration involves the elimination of water molecule from alkanol.
The two adjacent carbon atoms that bear the OH and His removed respectively resulting to the
formation of a double bond.
Ethanol dehydrates to give ethene

Propanol Propene
2. Dehydrohalogenation of Haloalkanes (Alkyl-halides, Rx)
This is the removal of hydrogen halide from the Haloalkanes. When a haloalkane is heated with
alcoholic solution of potassium hydroxide (KOH), the corresponding alkene is formed eg

Dehydrohalogenation of 2-bromopropane
H Br H
𝐾𝑂𝐻/𝐸𝑡ℎ𝑎𝑛𝑜𝑙
H–C–C–C–H→ CH3 – C = C – H + HCl
H H H H H
2- Bromopropane Propene
However, when 2-bromobutane is dehydrohalogenated, different molecules are formed. This is
because the adjacent hydrogen atom can be removed either from C1 or C3.
H Br H H H H H
𝐾𝑂𝐻/𝐸𝑡ℎ𝑎𝑛𝑜𝑙
H–C–C–C–C–H→ H–C–C–C=C–H or H – C – C = C – C – C – H
H H H H H H H H H H H H
But-1-ene But-2-ene
3. Industrial preparation of alkenes: the alkenes are produced commercially by cracking higher
alkanes. This is the breaking down of large alkane molecules in the petroleum fractions in the
pressure of a catalyst or heat.

Propane → Ethene and Methane

C3H8 → C2H4 + CH4

Decane → butane + Propene

C10H22 → C4H10 + 2C3H6

REACTIONS OF ALKENES
Alkenes have carbon to carbon covalent double bond this makes them very reactive. They usually
undergo addition reaction combustion, polymerization and substitution reactions.
1. Combustion: Alkenes burn with yellow luminous flame. This is because the proportion of
carbon to hydrogen is higher in alkenes than in alkanes.

C2H4 + 3O2 → 2CO2(g) + 2H2O

The general equation: CnH2n + 3(𝑛)O2 → nCO2 + nH2O

2

The reaction above is highly exothermic

Exercise : Balance C5H10 + O2 → CO2 + H2O
2. Addition reactions
a. Addition of Hydrogen gives a corresponding saturated (Alkane) hydrocarbon. Eg
𝐻2
Ethene → Ethane
𝐻2
Propene → Propane
CH2=CH2 +H2 → CH3CH3 Ethane
CH3CH=CH2 +H2 → CH3CH2CH3 Propane
b. Halogenation (Addition of halogen): This is the addition of halogens. The result becomes
halogenated alkanes or haloalkane.
X X
H – C = C – H + X2 → H – C – C – H where X= F2, Cl2, Br2, I2

H H H H
Ethene + Cl → 1,2-dichloroethane
 Alkene + Halogen → Halogenated Alkane
c. Addition of Hydrogen halides i.e. HCl, HBr, HI or HF H2C=CH2
+ HBr → H3C-CH2Br

Ethene + Hydrogen Bromide → MonoBromoethane

CH3-CH=CH2 + HBr→ CH3CHBrCH3 + CH3CH2CH2Br

2-bromopropane 1-bromopropane
The predominant product will be 2-bromopropane because the positive addendum is added to the
carbon atom that has a greater number of hydrogen atom. Hence, H atom is added to the terminal
carbon. This is Markownikoff’s rule- It states that the positive addendum is added to the carbon
atom that bears the greater number of hydrogen atoms. d. Reaction with bromine water
Alkenes decolorize the brown colour of bromine water by forming a colourless compound
(2bromoethanol) Halo alkanol.

H2C=CH2 + HOBr → CH2OH-CH2Br

e. Reaction with acidified KMnO4
Alkenes react with acidified KMnO4 to form a diol

Ethene + Acidified KMnO4 → 1,2-ethanediol or Ethan-1,2-diol f.

Reaction with water in the presence of H2SO4.
This reaction is known as hydrolysis of alkene. When alkenes are hydrolyzed, alkanols are
produced.
H H
𝐻−𝑂𝐻
H–C=C–H+→ H–C–C–H
𝐻2𝑆𝑂4

H H H H

Ethene + H2O → Ethanol

g. Hydrolysis of alkene in the presence of H3PO4 yields alkanol
H H
𝐻−𝑂𝐻 𝐻3𝑃𝑂4
H–C=C–H→ H–C–C–H
𝑠𝑡𝑒𝑎𝑚
 H H OH H
h. Reaction with O3 ionized water gives a mixture of alkanol. e.g.
H O O
𝑂3
H – C – C = C – H + H – OH → CH3CH + H – C – H
H H H Ethanal Methanal

Propene + steam → ethanol + methanol

3. Polymerization Reaction
This is the joining of small organic molecules (monomer) in a regular fashion to form a large
molecule called polymer.

Ethene +ethene → polyethene

Ethene polymerizes to yield polyethylene or polyethene
Alkenes can undergo substitution reactions to yield substituted alkenes egg with halogens to form
substituted Haloalkenes.
H H H H

C = C + 2Cl2 → C = C + 2HCl
H H Cl Cl

Ethene + Chlorine → 1,2-dichloroethene

ALKANOLS
Alkanols are a group of organic molecules with OH as their functional group. They conform to a
general formula CnH2n+1OH where n=1,2,3,4…. They can be represented as R-OH where R is
CnH2n+1 i.e. Alkyl radical.
They are derived from alkanes by dropping e and replacing it with ol. E.g.
Methane – Methanol – CH3OH
Ethane – Ethanol – C2H5OH
Propane – Propanol – C3H7OH
Butane – Butanol – C4H9OH
Pentane – Pentanol – C5H11OH
Hexane – Hexanol – C6H13OH
Heptane – Heptanol – C7H15OH
 CLASSIFICATION OF ALKANOLS
Alkanols can be classified according to the number of -OH group p per molecule i.e. 1,2,3, or 4 as
mono-ol, diol, triol and poly-ol respectively.
H H
eg H – C – C – OH ethanol i.e mono-ol
H H
H H
HO – C – C – OH ethan 1,2-diol or glycol
H H
OH OH OH
H–C–C–C–H propan-1,2,3-triol or glycerol/glycerine
H H H
OH OH OH OH
H–C–C–C–C–H butan-1,2,3,4-polyol.

H H H H
b. Another classification is based on the carbon atom that bears the OH-group. i.e. primary,
secondary or tertiary (alkanol-carbon)
i. The carbon atom at the terminals are called primary carbon. Hence, OH attached to such
carbon atom is called primary alkanol.
ii. The carbon atom attached directly to two other carbon atoms is called secondary carbon.
Thus, if the OH group is attached to such carbon atom, the alkanol is described as secondary
alkanol.
iii. The carbon atom that is directly attached to 3 other carbon atoms is known as tertiary carbon.
Therefore, if it bears OH group, the alkanol becomes tertiary alkanol.
Eg H H
H – C – C – OH primary ethanol
H H
H H H H
HO – C – C – C – C – H Primary butan-1-ol
H H H H
 H OH H
H–C–C–C–H Propan-2-ol secondary.
H H H
H OH H
H– C– C– C–H 2-methylpropan-2-ol.
H H–C–H H
H H
NOMENCLATURE IN ALKANOLS
The name of an alkanol is obtained by replacing the terminal e in the corresponding parent
hydrocarbon with -ol.
Procedure for IUPAC naming
The parent structure is the longest continuous chain of carbon atoms, which must include the
carbon at that bears the OH group. The number of carbon atom determines the parent name e.g.
2,3,4,5-ethanol, propanol, butanol or pentanol respectively.
The parent chain is numbered such that the carbon atom that bears the OH group has the lowest
possible number. The position of the functional group has preference over the position of multiple
bonds or substituents.
In naming, the position of functional group and substituents are specific e.g.
H OH H H OH H
H–C–C–C–H H–C–C–C–H
H H H H CH3 H
2-propanol or propan-2-ol 2- Methyl propan-2-ol
CH3 CH3 OH
CH3 – C – C – C – CH3
H CH3 H
3,4- dimethyl pentan-2-ol

H (CH2 – CH3)
C = C – CH2 – OH
H
2-ethyl prop-2en-1-ol
CH3 OH H
HO – C – CH2 – C – C – OH
H H H
Pentan-1,2,4-triol
ISOMERISM IN ALKANOLS
Isomerism occurs in alkanol which has at least three carbon atoms, unlike in alkanes, it starts from
at least 4 membered carbon
H H H H H H
H – C – C – C – OH H – C – C – C – OH
H H H H OH H
Propan-1-ol Propan-2-ol
H H H H H H H H
H – C – C – C – C – OH H–C–C–C–C–H
H H H H H H H H
ai. Butan-1-ol aii. Butan-2-ol

H CH3 H H CH3 H
H – C – C – C – OH
H–C–C–C–H
H H H
H OH H aiv. 2-
aiii. 2-Methyl propan-1-ol Methyl propan-2-ol
OPTICAL ISOMERS

Optical isomers have a particular way of reflecting light. Those that reflect it to the right are called
+ or d or dexorotatary while those that reflect to the left side are called lavo-rotatory.
 GENERAL PROPERTIES OF ETHANOL(ALKANOL)
1. Solubility decreases as the molecular mass increases. Lower members of alkanol dissolves in
water at all proportions but decreases with increase in carbon chain. i.e. Methanol > Ethanol >
Propanol > Butanol > Pentanol.
2. Boiling point of alkanol is higher than those of hydrocarbons because of inter-molecular
hydrogen bonding. Boiling point decreases as the branching increases because of crowding and
less inter-molecular hydrogen bond.
3. Boiling point increases as the molecular mass increases due to increased Vander Waal’s forces
between the molecules.
4. The straight chain alkanols have higher boiling points than their branched chain counter part
because, there is decrease in the hydrogen bonding in the branched chain due to crowding. i.e.
primary > secondary > tertiary

PREPARATION OF ALKANOL (ETHANOL)

1. Alkanol is prepared in the laboratory by hydration of alkene, using tetraoxosulphate VI acid
conc. as catalyst.
𝑐𝑜𝑛𝑐 𝐻2𝑆𝑂4
C2H4 + H2O → C2H5OH
Reaction mechanism
𝑐𝑜𝑛𝑐 𝐻2𝑆𝑂4
CH2=CH2 → CH3 – CH2 – OSO3 – H
CH3 – CH2 – OSO3 – H + H – O – H → CH3CH2OH + H2SO4
2. From Glucose (Fermentation): this is the breaking down of carbohydrates by the activity of
enzymes to produce ethanol and carbon IV oxide.
Enzymes: is a natural organic catalyst secreted by living cells
𝑧𝑦𝑚𝑎𝑠𝑒
C6H12O6→ 2C2H5OH + 2CO2 + heat
3. From Haloalkanes: React any haloalkane with an alkali a corresponding alkanol and metallic
halide will be obtained.

RX + NaOH → ROH + NaX

PROPERTIES OF ETHANOL – PHYSICAL
1. It is soluble in water because of hydrogen bonding
2. It has a pleasant odour with a burning taste or sensation
3. It is a liquid at room temperature. Its boiling point is at 78⁰C and freezes at -118⁰C 4. Its
solution in water is neutral and does not conduct electricity because there are no ions.
CHEMICAL PROPERTIES OF ETHANOL
1. It burns with blue flames producing carbon IV oxide and water

C2H5OH + 3O2 → 2CO2 +3H2O + heat

2. Ethanol reacts with alkali metals to liberate Hydrogen to form metallic alkoxide. It reacts with
metals in groups I, and II of the periodic table.
2C2H5OH + 2Na → 2C2H5ONa + 2H2
When any of the metals in groups I or II is dropped into a beaker containing ethanol, there is
effervescence, colourless, odourless, neutral gas is evolved, which burn in oxygen with pop sound.
The gas is Hydrogen.
In this reaction, ethanol behaves as an acid. It can be compared with the reaction of sodium with
cold water.
TEST FOR THE PRESENCE OF -OH groups
An organic molecule that reacts with alkali metal to liberate Hydrogen gas or with PCl 5 or SOCl2
to liberate HCl gas containing -OH group as in alkanol.

3. C2H5OH + SOCl2 → C2H5Cl(l) + SO2(g) + HCl(g)

Thionyl chloride (sulphur oxochloride)
4. Dehydration of Ethanol
Generally, an alkanol is dehydrated to give a corresponding alkene.
Dehydration of butan-2-ol gives a mixture of but-2-ene and but-1-ene. The reason is that one
molecule of water can be removed from two different positions.
5. Oxidation of ethanol
Primary alkanols are oxidized to alkanal first and finally to alkanoic acid. This occurs when an

alkanol is treated with acidified KMnO4 or K2Cr2O7. The oxygen supplied by the oxidizing agent

is written as [O].
Generally, primary Alkanols are oxidized to their corresponding alkanoic acids.

Secondary alkanols are oxidized to alkanones (ketones)

6. (IODOFORM) Triiodomethane Reaction

When iodine is dissolved in Sodium hydroxide solution, a characteristic yellow precipitate of

triiodomethane (iodoform) is obtained.

7. Formation of ether:

When an alkanol is treated with concentrated H2SO4 in the excess of the alkanol, an ether is formed

𝐻2𝑆𝑂4
e.g. C2H5OH + C2H5OH → C2H5OC2H5 + H2O 140℃

ROH + ROH → ROR + H2O

This is a dehydration reaction where the molecule of water is removed from two molecules of

ethanol. In this case, one of the molecules acts as an acid while the other acts as a base.

8. Esterification: This is a type of reaction between ethanol and carboxylic acid. The reaction is

usually catalyzed by a mineral acid. The reaction is reversible. The backward reaction is

hydrolysis.
 ATMOSPHERIC OXIDATION OF ETHANOL
Ethanol on exposure to the atmosphere, is slowly oxidized to ethanoic acid by the atmospheric
oxygen in the presence of bacteria. The sour taste of fruit juice, wine and beer is as a result of
atmospheric oxidation of these liquids when exposed, to ethanoic acid.
USES OF ETHANOL
1. It is used as an organic solvent
2. It is used in the production of moisturizing cream, soaps and drugs.
3. It is used as preservative in blood syrup/tonic.
4. For sterilizing surgical instruments
5. As fuel in racing cars
6. Alcoholic beverages
7. Thermometric liquid
8. Anti-freeze in car radiators
9. It is medicinal- being hypnotic
 DANGER IN ALCOHOLISM
If taken in strong doses, it leads to (loss of consciousness) dizziness followed by coma. Habitual
drinkers lose their value/respect.
1. It acts on the brain and nervous system
2. It can lead to Parkinson disease
3. It leads to loss of appetite, consequently loss of weight.
ALKYNES
Alkynes have general formula CnH2n-2 where n= 2.3. 4.. They are named by changing the -ane of
the alkane with -yne i.e C2H2 ethyne
C3H4 propyne C4H6
butyne
C5H8 pentyne
C6H10 hexyne
C7H12 heptyne
C8H14 octyne
C9H16 nonyne
C10H18 decyne
The first member is ethyne and it is prepared by reacting Calcium Carbide with cold water. CaC 2

+2H2O → C2H2 + Ca (OH)2

Ethyne is as dense as air. It is colourless and tasteless.
H-C≡C-H
It undergoes (1) Combustion (2) Addition (3) Polymerization reaction.
USES
1. It is used in welding of metals
2. It is used in the production of Benzene.
3. Test to distinguish classes of Alkanols
4. Lucas Reagent – Conc HCl and ZnCl2

TEST OBSERVATION INFERENCE

Tertiary alkanol + Lucas Immediate turbidity appears Presence of tertiary alkanol
reagent 2methylpropan-2-ol
Secondary alkanol + Lucas Turbidity appears five Presence of 2nd
reagent minutes after mixing alkanol- propan-2-ol
Primary alkanol + lucas No visible reaction Presence of 1⁰ alkanol
reagent (methanol)

Exercise:
1. State 2 similarities between the reaction of sodium with cold water and the reaction of
sodium with ethanol
2. Give the reagent and the reaction condition for the conversion of ethanol to ethyl ethanoate
3. Write an equation for the above conversion
CRUDE OIL
Summary of the chemical reactions of ethanol

POLYMERIZATION

Introduction

Polymerization is the process whereby small molecules of an organic compound combine

repeatedly, in a regular fashion, to form a long-chain molecule. The small molecules are called
monomers, while the product of polymerization is called polymer. A polymer is, therefore, a
longchain molecule obtained when monomers combine repeatedly. Polymers have high relative
molecular masses; hence, they are called macromolecules or giant molecules.

Polymerization takes place at high temperatures and pressures, and in the presence of catalysts.

Types of Polymerization Processes There

are two main types of polymerization:

a. Addition; b. Condensation.

Addition polymerization is treated in this section.

Addition Polymerization

Addition polymerization occurs in organic molecules containing carbon-carbon double covalent

bonds, as in alkenes, and those with triple covalent bonds, such as alkynes. In addition,
polymerization reactions, numerous monomers link in a highly regular fashion, to form a polymer
without a gain or loss of material. Under this condition, the monomer and the corres- ponding
polymer have the same empirical formula. For instance:

1. Polymerization of Ethene: Molecules of ethene polymerizes at high temperature and

pressure, and in the presence of a peroxide catalyst, to form polyethene (polythene):

The n molecules of ethene, nC2H4 and its polymer product - called polyethene, (C2H4)n have the
same empirical formula of CH2.

2. Polymerization of Ethyne: Three molecules of ethyne, C₂H₂ polymerizes in a cyclic

fashion, to give benzene, C6H6. Ethyne and benzene have the same empirical formula of CH.
Benzene is not a true polymer pro- duct, because n is too small:

Alkenes and their derivatives are raw materials for the production of plastics. In fact, ethene is the
major raw material in the plastics industry. Common examples of monomers, their addition
polymers, and general uses are listed in the table above. They are synthetic polymers (man-made).

PLASTICS AND NATURAL RUBBER

Nature of Plastics

Plastics are polymers whose molecules can slide over one another when stretched, with the
molecules remaining in their new positions when the stretching force is removed, i.e. for the
material to become deformed.

Plastics of all kinds are synthetic polymers. They are light, soft or hard, flexible, tough, and with
great tensile strengths. They are water proof, resist- ant to chemicals and heat. Plastics are
nonbiodegradable; hence, plastic wastes usually accumulate in the soil, and pollute the
environment.

Types of Plastics

Plastics are of two types: a. Thermoplastics; b. Thermosets. Thermoplastics Thermoplastics are

polymers that can be softened or melted when subjected to heat or pressure, and be remolded into
any shape. For such polymers, their plasticity (plastic property) increases as the heat or pressure
applied increases. Polyethene, polypropene and polystyrene are thermoplastics. Thermosets

Thermosets are polymers that cannot be softened or melted by heat or pressure. Once formed, they
become set (rigid), and cannot be remolded again. An example is polychloroethene (PVC).

NATURAL RUBBER

Introduction

Rubber-tree plantations are found in the southern part of Nigeria. When tapped, rubber trees give
a naturally occurring milky and sticky fluid - called latex. When latex is coagulated or smoked by
the use of methanoic or ethanoic acid, it gives raw rubber, which is tough, hard, and elastic. This
raw rubber can be masticated to give soft thread-like materials that can be molded into various
shapes. It is thermoplastic. Latex is an addition polymer of 2-methylbutadi- ene (isoprene); it is a
conjugated diene. Hence, the general molecular formula of latex is (C5H8)n. Other examples of
naturally occurring rubber are: cotton, wool, wood, and starch.

Synthetic Rubbers

Synthetic or artificial rubbers are obtained from 3-butadiene, and substituted 1,3-butadiene, e. g.
1. Chloroprene

Chloroprene, i.e. 2-chlorobutadiene polymerizes in the presence of sodium, to give a synthetic

rubber called neoprene
2. Buna-S

Buna-S is a synthetic rubber obtained by the co-polymerization of 1,3-butadiene and phenylethe-

ne (styrene).

Co-polymerization is a polymerization process involving two different monomers.

3. Buna-N

Buna-N is a synthetic rubber obtained by the co- polymerization of 1,3-butadiene 4 and

propenonitrile. Generally, synthetic rubbers are used in the pro- duction of motor tyres of all kinds.

VULCANIZATION OF RUBBER

Natural and synthetic rubbers are made harder, tougher and stronger by the process of
vulcanization.

In this process, a calculated quantity of sulphur is heated with raw rubber under pressure, so that
the sulphur atoms react with the carbon-carbon double bonds within the polymer chains; thereby,
forming cross-links of saturated sulphur-carbon bonds between the polymer chains - as shown
below.

Vulcanization is the process whereby natural rubber is heated with sulphur under pressure, in order
to obtain a harder, tougher and more elastic rubber.
The sulphur-carbon cross-links are responsible for the toughness, hardness, increased tensile
strength and elastic properties of rubber. They make vulcanized rubbers to be thermosetting
plastics.

The sulphur-carbon cross-links are responsible for the toughness, hardness, increased tensile
strength and elastic properties of rubber. They make vulcanized rubbers to be thermosetting
plastics. The quantity of sulphur used during vulcanization determines the elasticity of the rubber.
If a large excess of sulphur is added to the raw rubber, too many cross-links of sulphur-carbon
bonds are formed; they make the rubber to become an inelastic, but tough and hard solid called
ebonite, which is used in making motor tyres.

Petrochemicals

Petrochemicals are obtained from petroleum products as the starting raw materials. They are never
produced directly from petroleum or crude oil. For instance:
Ethanol is a petrochemical. It is obtained as shown in the following conversion scheme:

Petrochemicals serve as the raw materials for the production of plastics, artificial rubber, soaps,
per- fumes, nylon, Terylene, dyes, drugs, etc.

PETROLEUM PRODUCTS (FRACTIONS)

Petroleum products are the fractions obtained directly from the fractionating tower where the crude
oil has been refined by fractional distillation. The separation of petroleum fractions is based on the
differences in their boiling points. The main products or fractions are as listed in the table below.
 Uses of Petroleum Products (Fractions)

1. Petroleum (Refinery) gas

Petroleum (Refinery) gas is a mixture of methane, ethane, propane and butane.

Methane is used in the production of hydrogen.

Methane and ethane are used as industrial fuels.

A mixture of liquefied propane and butane is used in the laboratory, and as a household cooking
gas. It is sold as bottled gases under trade names Such as Nidogas, Eaglegas, and Sungas. All
gaseous alkanes are useful sources of heat, and raw materials for production of petrochemicals.

2. Gasoline (Petrol) or Petroleum ether

Petrol is a mixture of alkanes with chain-lengths of 5-10 carbon atoms.

• Used as fuel in vehicles and electric generators.

• As solvents for fats and oils. The fraction is sometimes called petroleum ether.

3. Paraffin Oil (Kerosene)

Kerosene is a mixture of alkanes with 11-15 car- bon atoms. It is much safer to use than petrol.

• It is the main fuel used in wick lamps (Lantern) for lighting purposes, and in cooking stoves.

• It is used as aviation fuels for aircrafts.

4. Gas Oil (Diesel Oil) or Fuel Oil Diesel oil or gas oil is a mixture of alkanes with chain-lengths
of 16 - 20 carbon atoms.

• Used as fuel in the engines of buses, trains, boats, tankers, ships, tractors and electric generators.
This fraction is sometimes called fuel oil.

5. Lubricating Oil

Lubricating oil is a mixture of alkanes with 20-30 carbon atoms; it is highly viscous.

• When redistilled, it produces greases (for engines and gearboxes), petroleum jelly (Vaseline),
engine oil, liquid paraffin, and wax - for candle making.

6. Residue (Bitumen) The black sticky residue left after the refining of crude oil is called bitumen
or asphalt.

• It is used in pitch or tar for roofing; as coatings for pipes; and when mixed with crushed rock
(coal tar), it is used for road surfacing.

Generally, petroleum products are the raw materials for the industrial production of many organic
chemicals; hence, the name petrochemicals. Ethan- ol, methanol, ethanediol, and ethanoic acid are
few.

CRACKING OF PETROLEUM PRODUCTS

What is cracking?
The quantity of petrol obtained from the fractional distillation of crude oil is about 20% by volume.
Cracking is employed as a source of alkenes, and to provide more petrol, since its demand is high.
Cracking is the process whereby large molecules of heavy oils are broken into smaller molecules
(light oils) at high temperatures and pressures, and in the presence of catalysts. Usually, petroleum
fractions with more than eleven carbon atoms in their molecules can be cracked. During cracking,
ethene, C₂H₄, the major raw material in the petrochemical industry, is produced.

Cracking Techniques

The three cracking processes are thermal cracking, catalytic cracking, and hydrocracking.

1. Thermal Cracking

Thermal cracking involves heating heavy oils, such as lubricating oil, diesel oil and kerosene, to
about 600 °C under pressure, for decomposition, and the formation of a mixture of more volatile
alkanes, alkenes and hydrogen. The mixture is then separated by fractional distillation, e.g.

2. Catalytic Cracking

In catalytic cracking, the heavy oil is heated to about 500 °C under reduced pressure, and in the
presence of natural clay [a mixture of SiO2 and AlO3] as the catalyst. Under these conditions, a
mixture of alkanes and alkenes, which can be separated by fractional distillation is obtained, e.g.

Note: The products of cracking depend on the starting materials, and the reaction condition.

3. Hydrocracking

In hydrocracking, hydrogen is passed into the mix- ture during the cracking process. Under this
condi- tion, only the lower saturated alkanes are obtained.

REFORMING TECHNIQUE

During reforming, straight-chain alkanes are converted catalytically, into branched-chain isomers,
cycloalkanes and benzene. The purpose is to convert low-grade petrol to higher grades, i.e. improve
the quality of petrol. Reforming technique includes isomerisation, cyclization and aromatization.
 CRACKING VERSUS REFORMING

1. Cracking involves breaking large molecules of petroleum fractions into smaller molecules, while
reforming involves rearrangement of atoms in the molecules of petroleum fraction to obtain
branched and cyclic hydrocarbons.

2. Cracking is achieved thermally or catalytically, while reforming is in the presence of a catalyst.

3. Cracking occurs at a temperature higher than that of reforming.

4. Cracking is employed to increase the quantity of petrol, while reforming is to improve its quality.

OCTANE NUMBER (OR RATING)

Each grade of gasoline (petrol) is rated according to the term octane number. Octane number or
rating is a value that indicates how smoothly a gasoline (petrol) burns in the engine of a vehicle.

Octane numbers are based on a scale on which 2,2,4-trimethylpentane (isooctane) is 100 (highest
grade petrol) and heptane is 0 (lowest grade petrol). Generally, branched-chain alkanes give higher
octane numbers than the straight-chain isomers. The percentage, in volume of
2,2,4trimethylpentane in a petrol determines its octane number. A 50:50 (or 1:1) mixture of heptane
and 2,2,4-tri- methylpentane gives petrol an octane number of 50 (medium grade). An increase in
the octane number of petrol leads to an increase in its energy value.

When petrol with a high proportion of heptane (low-grade) is used in the engine of a vehicle, the
combustion will not be smooth, and can knock (damage) the engine, while petrol with a high
proportion of the 2,2,4-trimethylpentane burns smoothly, and does not cause knocking. The higher
the octane number of petrol, the lower the knocking tendency.

In order to increase the octane number of a low- grade petrol and reduce engine wear, an additive,
tetraethyl lead (IV), Pb(C2H5)4 called antiknock together with calculated amounts of cycloalkanes
and benzene are added to petrol. However, the presence of antiknock in petrol is responsible for
the pollution of the atmosphere by lead compounds from the exhaust fumes of motor vehicles.

FATS AND OIL

Fats and oil are chemically similar except that oil is liquid at room temperature due to unsaturation
while fats are solid at room temperature because there is no double bond (it is saturated).
Oil is converted to margarine by boiling it up to 180oc in the presence of Nickel catalyst and
Hydrogen added at a presence of 5atm. This is called hardening of oil. Vitamins ADEK are added
to improve its nutritional value. Margarine is used in eating bread, white yam, rice, potatoes.
Vegetable oil + hot conc alkaline solution gives soap and glycerol.
Soap production: this is the alkaline hydrolysis of vegetable oil or saponification.

SOAP
To 50g of vegetable oil, add 20cm3 of 5molar sodium hydroxide solution, a few drops at a time.
Heat the mixture up to 90oc or 95oc with stirring vigorously during the process of saponification.
Continue stirring with glass rod until the whole solution has been emulsified into one layer. You
must have heated up to 15 minutes. Saponification is complete as soon as the mixture sticks to the
glass rod when withdrawn.
Transfer the content to a bigger container and add a solution of sodium chloride to enhance
precipitation of soap while boiling for 3 minutes to salt out. Cool the mixture and filter off the solid
transparent soap curd.
conclusion: Saponification of fats and oil followed by salting out process gives soap.
ACTION OF SOAP AS AN EMULSIFYING AGENT
If some cooking oil is poured into a beaker containing water, the oil will float on the water surface
as a separate layer. If the oil water mixture is shaken vigorously, the oil will be suspended as tiny
droplets in aqueous layer. This is called an oil-water emulsion.
The emulsion is unstable because the droplets coalesce to form the oil layer again on standing. If
the soap solution is added the soap molecules will crowd round the oil droplets. They are
hydrocarbon chain dissolves in the oil, while the ionic heads project into the surrounding water.
The electrostatic repulsion prevents the coalesce of the droplets into larger droplets, thus forming
a stable emulsion of the oil in water. Soap acts as an emulsifying agent.
 CYCLIC ALIPHATIC HYDROCARBON
These are compounds in which atoms of carbon are bonded together in a cyclic fashion – They are
called cycloalkanes if only saturated carbon atoms form the ring and cycloalkenes if there is at
least a carbon to carbon double bond within the ring of the carbon atoms. Monocycloalkanes have
the same general formula with the open-chain alkenes CnH2n. nevertheless n starts from 3. This
shows that monocycloalkanes have 2 hydrogen atoms less than the corresponding open chain
alkanes.
DETERMINATION OF OXIDATION NUMBER
Determination of oxidation number of each carbon in the following a) CH4 b) CH3Cl c) CH3OH
Inorganic reactions, oxidation is the addition of oxygen to or removal of Hydrogen from an organic
compound, while reduction is removal of O2 or addition of Hydrogen.
H= +1, O=-2, Halogen=-1, N=-3
CH4 (ON) C + 4(1)H = 0
(ON) C = -4
CH3Cl (ON) C + 3(1)H + (-1)Cl = 0
(ON) C + 3- 1 = 0
(ON) C + 2 = 0
C = -2
CH3OH (ON) C + 4(1)H + (-2)O = 0
(ON) C + 2 = 0
C = -2
a) CH2=CH2 b) CH3COOH
The 2C are equal
2(ON)c + 4(ON)H = O
2(ON)c + (ON)c-c + 2(ON)o = 0
C+ 0 + 2(-2) + 1 = 0
(ON)c -4 + 1 = 0
-3 = 0
:.(ON)c = +3
 HARD WATER AND SOAP
Hard water contains dissolved salts of magnesium and calcium or iron III. These ions in hard wate
react with soap to form grey insoluble salt called scum.

Ca2+ + 2(CH3(CH2)16COO- → [CH3(CH2)16COO-]2Ca(s)

In hard water in soap calcium octadecanoate
The formation of scum between soap and calcium ions is a limitation to the use of soap with hard
water. This prevents the soap from forming foam. Hence, hard water wastes soap, since a large
quantity of the soap must be used before lather is produced.
ACIDIC WATER AND SOAP
Soap RCOONa+ is a salt of weak acid. In an aidic water, the anion RCOO-, combines with H+ from
the acid water to form RCOOH; hence, reduces the concentration of RCOO- in the H2O reducing
the cleansing power of soap.
DETERGENT – SOAPLESS
These are cleansing agents like soap. They are sodium or potassium salt of long-chain alkyl
hydrogen tetraoxosulphate (VI). R-OSO3H. they are synthesized by sulphonating alkene and fatty
acids.
Stage 1- An alkul that has C16 or C18 is treated with conc tetraoxosulphate (VI) obtained from
cracking of petroleum fraction or dehydrating long-chain alkanols.
R – CH = CH2 + HOSO3H → RCH – CH3 (addition reaction)
OSO3H
Stage II- The sulphonated long-chain alkene is qualitatively treated with sodium/ potassium
hydroxide in order to obtain a sulphonated salt of long-chain alkyl Hydrogen tetraoxosulphate (VI)
H
R – C – CH2 + NaOH(aq) → RCH – CH3 + H2O
OSO3H OSO3-Na+
SOAP DETERGENT
Is the sodium salt of long-chain carboxylic acid Is sodium/potassium salt of a long-chain alkyl
represented as RCOO-Na+ hydrogen tetraoxosulphate (VI) represented as
ROSO3-Na+
Produces an insoluble grey salt with hard Produces soluble salt of magnesium or calcium
water even when used with hard water
 ALKANOIC ACIDS
These are inorganic compound with functional group in which an hydroxyl group -OH, is bonded
to carbon atom of the carbonyl group to give – C = O

OH
The functional group is called carboxylic group, usually written as -COOH or CO2H.
Organic acids with one carboxylic group per molecule are called monocarboxylic acids. The
structure is represented as R-COOH for saturated aliphatic monocarboxylic acid.
HOMOLOGOUS SERIES IN ALKANOIC ACIDS
CnH2n+1COOH where n= 0,1,2,3,4, etc.
In the 1st homologue, n= 0, since one carbon atom is in the functional group, the formula will be
HCOOH.
O
H – C – OH

Second member is where n=1→ CH3COOH. The third member corresponds to n=2,
CH3CH2COOH or C2H5COOH. They are named after the corresponding alkane by dropping the e
in the parent alkane and replacing with oic acid. Hence, the first member is methanoic acid, 2nd
member is ethanoic acid and so on and so forth.
Exercise
Find the molecular mass of an organic acid whose formula is CH2O2
a) 60 b) 45 c) 38 d) 73 e) 50
IUPAC Nomenclature
The parent name is derived from the longest continuous chain of carbon including the carbon atom
in the functional group.
Numbering starts from the parent chain, the carbon in the carboxylic group. Hence, no need
indicating the number of positions of the functional group in the nae assigned. e.g.
CH3CH – CH2COOH 3-Methylbutanoic acid

CH3

CH3C(CH3)2COOH 2,2-dimethylpropanoic acid

H H
C=C
CH3 COOH

CH3
CH3 – C = C – CH – COOH 3-Chloro 2-ethyl 4-methyl 3 pentenoic acid
Cl C2H5
O O

HO – C – C – OH Ehanedioic acid C2H2O4

H3C COOH
C=C
HOOC CH3
Exercise
1i. Write the IUPAC name for CH3CHCH3CO2H ii.
Give its molecular formula
iii. Calculate the % of O2 by mass in the compound
[H= 1, C= 12, O= 16]
2i. An alkanoic acid contains 48.7% carbon,8.11% hydrogen.
ii. Calculate its empirical formula iii. If its relative molecular mass is 64, determine its molecular
formula and write its IUPAC name.