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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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