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ORGANIC CHEMISTRY
Alkanes

What are the characteristics of a homologous series?

o They can be represented by a general formula.

o There is a common difference of CH2 between successive members.

o The can be prepared by a general method.

o They show the same chemical reactions.

o Gradation in physical properties down a series as there an increase in the


size and mass of the molecules. Melting point, boiling point and viscosity
increases whereas flammability decreases.

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Alkanes is a homologous series of saturated hydrocarbons with the general
formula, CnH2n+2. They are obtained from petroleum (crude oil).

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Examples of Alkanes:
Methane Ethane

Propane

Butane

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Pentane

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Isomerism

Compounds having the same molecular formula but different structural


formulae are said to exhibit isomerism.

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Isomers of C2H4Cl2

Isomers of C2H5OH

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Isomers of C4H10

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Isomers of C5H10

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Isomers of C4H8

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Alkanes are generally unreactive except in terms of:

(a) Burning or Combustion

Alkanes burn in plentiful supply of air to form carbon dioxide and water. They
burn with a blue flame.

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

C5H12(g) + 8O2(g)  5CO2(g) + 6H2O(l)

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(b) Substitution by Chlorine (presence of sunlight is required)

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Alkenes

Alkenes is a homologous series of unsaturated hydrocarbons (because of carbon


double bonds) with the general formula, CnH2n. They are obtained from
petroleum (crude oil).

Ethene Propene

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Butene Pentene

Isomers of Pentene

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Alkenes undergo addition reactions because of the double bond.

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1. Burning or Combustion

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

They burn with a yellow flame.

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2. Addition of halogens (chlorine or bromine)

3. Addition of hydrogen

Conditions: Nickel catalyst


200oC

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4. Addition of steam/water

Conditions: Phosphoric Acid catalyst


300oC

How would you distinguish between alkanes and alkenes?

Alkenes decolourises bromine water (reddish-brown to colourless) whereas


alkanes show no visible reaction with aqueous bromine.

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What is cracking?

Cracking is the process whereby long-chain hydrocarbon molecules are broken


down into simpler and more useful molecules.

C22H46  C6H14 + 8C2H4

Uses of cracking:

(a) Manufacture of alkenes


(b) Manufacture of hydrogen
(c) Manufacture of gasoline

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Manufacture of Margarine

Margarine is made by hydrogenating unsaturated vegetables oils to form a solid


product.

If there aren't any carbon-carbon double bonds, the substance is said to be


saturated.

If there is only one carbon-carbon double bond in each of the hydrocarbon


chains, it is called a mono-unsaturated.

If there are two or more carbon-carbon double bonds in each chain, then it is
said to be polyunsaturated.

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Alcohols

Alcohols is a homologous series containing the –OH group. They have the
general formula CnH2n+1OH.

Methanol Ethanol

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Propanol and its isomer

Butanol and its isomers

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Pentanol and its isomers

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(a) Combustion

C2H5OH + 3O2  2CO2 + 3H2O

(b) Oxidation to ethanoic acid

Ethanol + oxidising agent  ethanoic acid + water

Condition: Either
(i) heat with acidified potassium manganate (VII) OR
(ii) heat with acidified potassium dichromate (VII) OR
(iii) atmospheric oxygen (the reaction is slower)

(c) Production of ethanol by fermentation


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Yeast is added to aqueous glucose. The temperature is kept around 35oC.


Ethanol and carbon dioxide are produced. Ethanol is then obtained from this
solution by fractional distillation.

C6H1206  2C2H5OH + 2CO2

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(d) Production of ethanol from ethane

Conditions: Phosphoric Acid catalyst


300oC

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Uses of Ethanol

(a) As a constituent of alcoholic beverages (e.g. wine and beer)

(b) As a renewable fuel in cars

(c) As a solvent for aftershaves and nail varnishes

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Carboxylic Acids

Carboxylic Acids is a homologous series containing the –CO 2H group. They


have the general formula CnH 2n+1COOH. They are weak acids. They turn damp
blue litmus paper red.

Methanoic acid Ethanoic acid

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Propanoic acid Butanoic acid

(a) Liberates hydrogen from reactive metals

2CH3COOH + 2Na  2CH3COO–Na+ + H2

(b) Liberates carbon dioxide from carbonates

2CH3COOH + CaCO3  (CH3COO)2Ca + CO2 + H2O


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(c) React with bases and alkali to form salt and water

CH3COOH + NaOH  CH3COO–Na+ + H2O

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(d) Esterification

(i) Ethanol + ethanoic acid  ethyl ethanoate + water

C2H5OH + CH3COOH  CH3COOC2H5 + H2O

+ 

Conditions: heat with a little concentrated sulphuric acid


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(ii) butanol + propanoic acid  butyl propanoate + water

C4H9OH + C2H5COOH  C2H5COOC4H9 + H2O

(iii) propanol + butanoic acid  propyl butanoate + water

C3H7OH + C3H7COOH  C3H7COOC3H7 + H2O

Uses of Esters (Esters are sweet smelling liquids)

(i) used as artificial flavour in sweets, cakes and fruit juices


(ii) used a solvent for nail varnish

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Macromolecules

Macromolecules are large molecules built up from small units, different


macromolecules having different units and/or different linkages.

Addition polymerisation occurs when identical monomer molecules join


together to form only one product (a polymer). The product has the same
empirical formula as the monomer.

Example 1:
Poly(ethene) or polyethene

Poly(ethene) is used for the manufacture of plastic bags.

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Example 2:

Poly(chloroethene) or polyvinylchloride (PVC)

Uses of PVC
1. Manufacture of plastic water pipes
2. For coating fabrics to make them waterproof
3. Used as electrical insulator

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Condensation polymerisation occurs when two or more different


monomer molecules join together to produce a polymer and other small
molecules.

Example 1
Nylon (Polyamide)

Polyamides such as nylon are condensation polymers. Both the amine and the
acid monomer units each have two functional groups - one on each end of the
molecule. In this polymer, every other repeating unit is identical.

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Nylon is very similar to the protein polyamides in silk and wool, but is stronger.
more durable, more chemically inert, and cheaper to produce than the natural
fibers.

Nylon is often simply represented as:

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Uses of nylon
(a) To make hard-wearing fabrics
(b) To make strong ropes (Polyurethane)

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Example 2

Terylene (Polyester)

Polyesters such as PET (polyethylene terephthalate) are condensation polymers.


The formation of a polyester follows the same procedure as in the synthesis of a
simple ester. The only difference is that both the alcohol and the acid monomer
units each have two functional groups - one on each end of the molecule. In this
polymer, every other repeating unit is identical.

PET is made from ethylene glycol and terephthalic acid by splitting out water
molecules (-H from alcohol and -OH from acid as shown in red on the graphic).
The units are joined to make the ester group shown in green.

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Terylene is often simply represented as:

Uses of terylene
(a) Used as substitutes for cotton (Dacron clothing) and wool in the textile
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(b) Used as the bonding resin in glass fibre plastics
(c) Made as tape (Mylar) which is magnetically coated for use in tape recorders
and videotape machines

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Synthetic fibres are said to be non-biodegrable i.e. they cannot be broken into
simpler substances by bacteria. Thus, it is not easy to dispose (get rid of) them.
One method is by burning them but here they produce harmful combustion
products like CO, soot and HCl (PVC).

The main macromolecules found in foodstuffs are:


(a) Proteins
(b) Fats
(c) Carbohydrates

Proteins

o Proteins possess the same amide linkages as NYLON but with different
units.

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o Proteins are formed by the condensation of amino acids.

o Proteins can be broken back into amino acids by refluxing the protein
with dilute hydrochloric acid.

o Amino acids can be separated by chromatography. Because amino acids


are colourless, the position of each amino acid is found using a ‘locating
agent’. This is sprayed over the chromatogram and produces a coloured
product. The colours are then compared to a standard chart to deduce the
amino acids present.

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Fats

o Fats are ester molecules possessing the same linkages as Terylene but
with different units.

o Fats are formed by the condensation of glycerol and fatty acids.

o Fats can be broken back into glycerol and fatty acids by boiling with
aqueous NaOH.

Lard + NaOH  Soap + Glycerol

Fat + alkali  carboxylic salt + alcohol


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Structure of a fatty acid

Structure of a soap

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Structure of glycerol

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Carbohydrates

o Starch is formed by the condensation polymerisation of smaller


carbohydrate units called sugars (glucose).

o Starch can be broken down into sugars (glucose) by boiling with dilute
hydrochloric acid.

o Starch can also be broken down by natural catalysts called Enzymes.


Amylase converts starch to maltose.

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Starch is a macromolecule represented as:

Structure of a sugar (glucose)

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Fuels

 Petroleum, coal and natural gas are natural sources of fossil fuels.

 Methane is the main constituent of natural gas.

 Petroleum is a mixture of hydrocarbons. It can be separated into useful


fractions by fractional distillation.

Fractions Uses
Butane  Bottled gas for cooking

Petrol (Gasoline)  As fuel in motor vehicles engine


 Cigarette lighter fuel
Kerosene (Paraffin)  Oil stoves for cooking
 Aircraft fuel
Diesel oil  For fuel in diesel engine e.g. lorries, buses and
ships
Lubricating oil  As lubricants in moving parts of machinery
 Making waxes and polishes
Bitumen  For making roads

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