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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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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) C5H12(g) + 8O2(g)
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CO2(g) + 2H2O(l) 5CO2(g) + 6H2O(l)

(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)
They burn with a yellow flame.
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2CO2(g) + 2H2O(l)

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
Uses of cracking:
(a) (b) (c) Manufacture of alkenes Manufacture of hydrogen Manufacture of gasoline

C6H14 + 8C2H4

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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 (b) Oxidation to ethanoic acid
Ethanol + oxidising agent

2CO2 + 3H2O

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
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(CH3COO)2Ca + CO2 + H2O

(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
(iii) propanol + butanoic acid

C2H5COOC4H9 + H2O

propyl butanoate + water

C3H7OH + C3H7COOH

C3H7COOC3H7 + H2O

Uses of Esters (Esters are sweet smelling liquids) (i) (ii) used as artificial flavour in sweets, cakes and fruit juices 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 industry education.mu/chemistry (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
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carboxylic salt + alcohol

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