CHEMISTRY 5072/02 SYLLABUS

ORGANIC CHEMISTRY

11.1 Fuels and crude oil

Source of energy
 Natural Gas (mainly methane)
 Petroleum- A mixture of hydrocarbons

It is separated into the following useful fractions:

Fractions Uses
Petrol (Gasoline) Fuel in cars
Naphtha Feedstock for the chemistry industry
Paraffin (Kerosene) Fuel for heating and cooking and for
aircraft engines
Diesel Diesel engines
Lubricating Oil Source of polishes and waxes
Bitumen Making road surfaces

Naphtha is the main source of hydrocarbons used for the production of a wide range of organic
compounds.

Given the finite quantity of fossil fuels, there are competing uses of crude oil as an energy source as
well as a chemical feedstock.

11.2 Alkanes

 Alkanes are a homologous series as a group of compounds with a general formula, similar
chemical properties and showing a gradation in physical properties as a result of increase in
the size and mass of the molecules.
 An homologous series of saturated hydrocarbons with the general formula C nH2n+2

Name of Formula Structure of branched Structure of unbranched alkanes

Alkane of Alkane alkanes
Methane CH4 None
H
H C H

H
Ethane C2H6 None
H H
H C C H

H H
 Propane C3H8 None
H H H
H C C C H

H H H
Butane C4H10
H
H H H H
H C H
H H H C C C C H
H C C C H H H H H
H H H
Isomerism- It is when two or more molecules have the same molecular formula, but different
structural formula. They may or may not have similar chemical properties depending on whether
they have the same functional groups.

Alkanes are saturated as they already possess the maximum number of hydrogen atoms that can be
added to the carbon chain. Hence, they are generally inert except when burnt and undergo
substitution by chlorine.
Combustion of alkane (Methane):
CH4 + 2O2 → CO2 + 2H2O
Substitution by chlorine:
 Conditions: Presence of Ultra-violet light and a halogen reactant.
CH4 + Cl2 → CH3Cl + HCl

11.3 ALKENES

 Alkenes are a homologous series of unsaturated hydrocarbons with the general formula
CnH2n.

Name of Formula Structure of branched alkene Structure of unbranched alkenes

Alkene of
Alkene
Ethene C2H4 None
H H
Propene C3H6 None
H HC H C H H
H C C C H

H
 Butene C4H8
H

H C H
H H
H C C C H

H
Catalytic cracking of crude oil is a process in which longer-chain hydrocarbons are converted to
shorter-chain hydrocarbons and hydrogen gas, through the use of heat and a catalyst.
Conditions:
 400°C to 600°C
 Al2O3 or SiO2 catalyst

The catalytic cracking of large hydrocarbons always produces an alkene with other possible by-
products such as alkanes and hydrogen.
Cracking of crude oil is essential because smaller fractions are in higher demand than larger
fractions. Hence, larger hydrocarbon molecules can be put through catalytic cracking to meet the
high demand.

Saturated compounds have a C-C bond in their molecular structure while unsaturated compounds
have a C=C bond in their molecular structure.
When shook with brown aqueous bromine, alkanes do not decolourises bromine.
When shook with brown aqueous bromine, alkenes decolourises bromine.

Alkenes are generally reactive as they have a C=C bond.

They undergo:
 Combustion
 Addition reactions
 Addition of hydrogen
 Addition of steam
 Addition of halogen
 Addition polymerisation

Combustion of alkenes: C2H4 + 3O2 → 2CO2 + 2H2O

Addition of hydrogen: C2H4 + H2 → C2H6
Conditions:
 Hydrogen reactant
 Nickel catalyst
 200°C
Addition of steam: C2H4 + H2O→ C2H5OH
Conditions:
 Steam reactant
 H3PO4 catalyst
 300°C
 60 atm
Addition of halogen: C2H4 + Br2→ C2H4Br2

Polyunsaturated food means that the food contains more than one C=C bond in the food. Hence, they
are easier to be broken down.

Vegetable oils, which are liquids at room conditions, need to be solidified to make margarine. By the
addition of hydrogen, some C=C bonds are removed. This raises the melting point of the vegetable
oil, hence solidifying it.

11.4 Alcohols

 Alcohols is a homologous series containing the –OH functional group.

Name of Formula of Alcohol Structure of unbranched Alcohols

Alcohol
Methanol CH3OH
O
Ethanol C2H5OH

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

H H H
Butanol C4H9OH
H H H H

H C C C C O H

H H H H
Alcohols undergo:
 Combustion
Products: Carbon dioxide and Water Vapour
 Oxidation
Products: Carboxylic acids and water
Alcohols are able to oxidize into carboxylic acids in atmospheric oxygen or the presence of an
oxidizing agent.
Alcohols are formed through:
 Addition of steam to alkenes
 Fermentation of glucose

Addition of steam: C2H4 + H2O → C2H5OH (With catalyst of H3PO4)

Fermentation of glucose: C6H12O6 → 2C2H5OH+ 2CO2

Fermentation is the conversion of glucose into ethanol with a yeast catalyst, a temperature of about
37°C and the absence of air and light

Uses of ethanol
 Solvent
 Fuel
 Constituent of alcoholic beverages

11.4 Carboxylic Acids

 Carboxylic acids is a homologous series containing the –COOH- functional group

Name of Formula of Carboxylic Structure of unbranched Carboxylic Acids

Carboxylic Acid Acids
Methanoic Acid HCOOH
O
Ethanoic Acid CH3COOH
H O
H C O H
H C C O H

H
Propanoic Acid C2H5COOH
H H O
H C C C O H
H H
Butanoic Acid C3H7COOH

H H H O
H C C C C O H
H H H
Carboxylic acids are weak acid as only a percentage of its acid molecules dissociates to
produce H+ ions when dissolved in water, leaving some carboxylic acid molecules
undissociated.
Carboxylic acids are able to react with carbonates, bases and some metals.

Ethanonic acid is formed by the oxidation of ethanol by atmospheric oxygen or acidified potassium
dichromate (VI).
Oxidation of ethanol: C2H5OH + 2[O] → CH3COOH + H2O

Carboxylic acids (e.g. ethanoic acid) and alcohols (e.g. ethanol) can react together to form esters (e.g.
Ethyl ethanoate).
Esterification: CH3COOH + C2H5OH→ CH3COOC2H5

Commercial uses of esters

 Perfumes
 Flavourings
 Solvents

11.6 Macromolecules

 Macromolecules are large molecules built up from small units, different macromolecules
having different units and/or different linkages.

Addition polymerization of ethene to form poly(ethene):

nH C C H

H H

H H
C C
H H

Many small unsaturated organic molecules of ethene combine with other ethane molecules to
form a large saturated macromolecule poly (ethene) as a single product.

Uses of poly(ethene):
 Plastic bags
 Clingflim

(Skipped part (d))

Nylon, a polyamide, and Terylene, a polyester, are condensation polymers as they are formed from
many small organic molecules which have combined together to form a large macromolecule with
the elimination of one inorganic molecule per linkage formed.
Uses of nylon and Terylene:
 Clothing
 Curtain
 Materials
 Fishing line
 Parachutes
 Sleeping bags

Non-biodegradable plastics cannot decompose naturally and hence lead to land pollution and lack of
space when buried in landfills.