ORGANIC CHEMISTRY
DR.SML
IIP INTERNATIONAL SCHOOL SCIENCE DEPARTMENT
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Organic Chemistry
Introduction to organic chemistry
Organic compounds = carbon-containing compounds (except for the very simplest)
Carbon’s unique properties-
✓ carbon atoms can join to each other to form long chains
✓ carbon atoms in a chain can be linked by single, double or triple covalent bonds
✓ carbon atoms can also arrange themselves in rings
Organic
compounds
Hydrocarbon
-molecules
that contain
carbon and
hydrogen only
saturated unsaturated
hydrocarbons hydrocarbons
Saturated hydrocarbon = hydrocarbon molecules in which all the carbon-carbon bonds are
single covalent bonds
Unsaturated hydrocarbon = hydrocarbons whose molecules contain at least one C-C double
or triple bond (not all C-C bonds are single)
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Types of formulae for organic molecules
-Empirical formula – simplest whole number ratio of the atoms in a compound
-Molecular formula – the actual number of each type of atom present in a molecule
-General formula – a type of empirical formula that represents the composition of any member of
an entire class of compounds
-Structural formula – shows how the atoms in a molecule are joined together
• Displayed formula – a representation of the structure of a compound that shows all the atoms
and bonds in the molecule
• Condensed form – by omitting all the C-C single bonds and C-H single bonds
Homologous series
- a family of similar compounds with similar chemical properties due to the presence of the same
functional group
eg. Alkanes (methane, ethane, propane, etc.)
Properties of homologous series
▪ Same functional group
▪ Similar chemical properties
▪ Show a trend in physical properties
▪ Same general formula
▪ Differ from the next by a -CH2- unit
▪ Similar method of preparation
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➢ Functional group
- an atom or group of atoms that determines the chemical properties of a compound (OR)
responsible for the characteristic reactions of a compound
➢ Naming and writing chemical formulae of organic compounds
Number of Prefix to name Alkane Alkene
carbon atoms Suffix(-ane) Suffix(-ene)
1 meth- methane methene
2 eth- ethane ethene
3 prop- propane propene
4 but- butane butene
5 pent- pentane pentene
6 hex- hexane hexene
7 hept- heptane heptene
8 oct- octane octene
9 non- nonane nonene
10 dec- decane decene
*IUPAC naming system* (International Union of Pure and Applied Chemistry)
-The product has 2 carbon atoms joined by a single bond. So it is named after ethane.
-The molecule contains 2 bromine atoms. It is called dibromoethane.
-The bromine atoms are attached to the different carbon atoms. The carbon atoms
numbered 1 and 2. The full name of the compound is 1,2-dibromoethane.
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Structural isomerism
-molecules with the same molecular formula, but different structural formulae.
*Isomers of C5H12
*Isomers of butene
Structural isomerism can be shown by members of any homologous series and can arise from changing
the position of functional group in a molecule.
They have very similar chemical properties as they have the same functional group.
Hydrocarbons containing branched chains have lower m.p and b.p than straight-chain compounds
with the same number of carbon atoms.
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Alkanes
-saturated hydrocarbons
-used as fuels
-methane – major component of natural gas
-propane and butane – LPG (liquefied
petroleum gas)
-first 4 members are gases (C1 to C4), next are
liquids (C5 to C17), from C17 onwards are solids
-General formula = CnH2n+2
Chemical properties
Alkanes are fairly unreactive.
1.Combustion
In excess air, complete combustion – produces CO2 and H2O
CH4 + O2 CO2 + H2O
If isn’t enough air, incomplete combustion – produces C or CO and H2O
2CH4 + 3O2 2CO + 4H2O
2.Substitution (Chlorination)
A reaction in which an atom (or atoms) of a molecule is replaced by different atom(s), without changing the
molecule’s general structure.
methane + chlorine sunlight chloromethane + hydrogen chloride
CH4 + Cl2 CH3Cl + HCl
Methane and chlorine react in the presence of sunlight or a source of UV light. The reaction is called
photochemical reaction. The UV light provides the activation energy (Ea) for the reaction and split chlorine
molecules into separate energised atoms.
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Cracking
-a process in which long-chain alkanes are converted to alkenes and shorter-chain alkanes
Types – thermal cracking and catalytic cracking
In cracking, larger molecules from the heavier fractions (obtained from petroleum) can be broken down into
smaller, more valuable, molecules.
Cracking is an example of thermal decomposition.
Conditions – temperature = around 500 ˚C
catalyst = alumina(Al2O3), silica(SiO2), zeolite
decane octane + ethene
C10H22 C8H18 + C2H4
ethane ethene + hydrogen
C2H6 C2H4 + H2
A cracking reaction can give:
✓ An alkane with a shorter chain than the original
✓ A short-chain alkene
✓ hydrogen
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Alkenes
-unsaturated hydrocarbons (contain double bonds C=C)
-physical properties are very similar to those of alkanes
-General formula = CnH2n
-First member is ethene.
Chemical properties
The presence of C=C bond in alkene makes
them more reactive than alkanes.
1. Combustion
ethene + oxygen carbon dioxide + water
C2H4 + 3O2 2CO2 + 2H2O
2. Addition
- a reaction in which a part of double bond breaks to become a single C-C bond. (only one product is formed)
❖ Halogenation (Bromination)
Addition of bromine to alkene can be used as test for unsaturated.
ethene + bromine 1,2-dibromoethane
CH2=CH2 + Br2 CH2BrCH2Br
(orange) (colourless)
❖ Hydrogenation
150-300˚C
ethene + hydrogen ethane
nickel
C2H4 + H2 C2H6
❖ Hydration (manufacture of ethanol)
ethene + steam ethanol
C2H4 + H2O C2H5OH
Catalyst = immobilised H3PO4 phosphoric acid
Temperature = 300 ˚C
Pressure = 6000 kPa
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Alcohols (alkanols)
-General formula = CnH2n+1 OH
-functional group = -OH
Production of ethanol
1. Hydration of ethene
2. Fermentation (from glucose)
Fermentation
-Industrial process
-Conditions – temperature – 25-35˚C
catalyst – yeast
glucose – aqueous
anaerobic
C6H12O6 2 C2H5OH + 2 CO2 (self-limiting)
(14%)
Uses of ethanol
-As a solvent: Ethanol is important solvent
and a raw material for making other
organic chemicals.
-As a fuel: Ethanol is a biofuel. It can be
mixed with petrol or used alone as a fuel
for cars.
-It is used to make other chemicals such
as esters.
-Ethanol produced by fermentation is used
for making alcoholic drinks.
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Carboxylic acids
-General Formula = CnH2n+1COOH
-Functional group = -COOH
Formation of ethanoic acid
1.Oxidation of ethanol with acidified
potassium manganate(VII)
Ethanol + oxygen ethanoic acid + water
C2H5OH + 2[O] CH3COOH + H2O
2. Biochemical oxidation
-bacterial oxidation of ethanol (wine) into ethanoic acid (vinegar)
-Acetobacter bacteria are naturally occurred in air and responsible for this bacterial oxidation
Properties of carboxylic acids
-weak acids (pH 3-5)
1. reaction with metal
2CH3COOH + Mg (CH3COO)2Mg + H2
2. reaction with metal hydroxide
CH3COOH + NaOH CH3COONa + H2O
3. reaction with metal carbonate
CH3COOH + Na2CO3 CH3COONa + H2O + CO2
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Esters
-functional group = -COO-
-formed when alcohol reacts with carboxylic acid(esterification)
-sweet-smelling oily liquids
Uses
-food flavourings and perfumes (volatile liquids)
-naturally occurring in many fruits and flowers where they are
responsible for flavours and scents
Esterification
Reactants – alcohol and carboxylic acid
Catalyst – concentrated H2SO4
Conditions – heat
Ethanoic acid + ethanol ethyl ethanoate + water
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
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Petrochemicals and polymers
➢ Petroleum and its products
- one of the fossil fuels
- non-renewable and finite resource
- complex mixture of many different hydrocarbons
- can be used as chemical feedstock and are separated by refining (fractional distillation)
- crude oil is heated until it boils and the vapours pass into a fractionating column, which is cooler at the top
and hotter at the bottom
As the molecules become bigger,
▪ Boiling point increases
▪ Less volatile
▪ More viscous
▪ Daker in colour
▪ Do not burn easily (flammability
decreases)
The different fractions obtained from
fractional distillation of crude oil are
useful.
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➢ Polymers
- large organic macromolecules and are made up of many small repeating units known as monomers
joined together by polymerisation.
Types of polymers
❖ Natural and synthetic polymers
❖ Homopolymers and copolymers
❖ Addition and condensation polymers
- Monomer = a small molecule that can be polymerised to make a polymer
Polymerisation
- a chemical reaction in which molecules (monomers) join together to form a long-chain polymer
1. Addition polymerisation
- alkene (C=C) will undergo addition polymerisation
- double bonds open up and becomes single bond
From monomer to polymer From polymer to monomer
• Draw the monomers with their double bonds • Identify the repeating unit – it will have two
next to each other carbon atoms with a single bond between
• Remove the double bonds and draw single them; put a bracket around it
bonds in the space between the monomers • Draw that unit as a separate molecule with a
double bond in it
Polymer Monomer Properties Examples of use
Poly(ethene) PE ethene tough, durable plastic bags, bowls,
CH2=CH2 bottles, packaging
Poly(propene) PP Propene tough, durable crates and boxes, plastic
CH3CH=CH2 rope
Poly(chloroethene) PCV chloroethene strong, hard (not as insulation, pipes and
CH2=CHCl flexible as PE) guttering
Poly(tetrafluoroethene) tetrafluoroethene Non-stick surface, non-stick frying pans, non-
PTFE CF2=CF2 withstands high stick taps and joints
temperatures
Poly(phenylethane) PS phenylethene light, poor conductor of insulation, packaging
C6H5CH=CH2 heat (foam)
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2.Condensation polymerisation
- a reaction in which two molecules react together to form a new, larger molecule with the elimination of a
small molecule, usually water.
Types of condensation polymers
-polyamide (Natural = proteins, synthetic = nylon)
-polyester (Natural = fats, synthetic = terylene)
❖ Nylon (Polyamide) Terylene (Polyester) PET
monomers = diamine and dicarboxylic acid monomers = diol and dicarboxylic acid
linkage = amide linkage linkage = ester linkage
❖ Natural polymers (proteins)
monomers = amino acids (20 different amino acids)
linkage = amide (peptide) linkage
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Comparing addition and condensation polymerisation
Addition polymerisation Condensation polymerisation
Usually many molecules of a single Molecules of two monomers usually
monomer used
Monomers used Monomer is unsaturated (C=C bond) Monomers contain reactive functional
groups at ends of each molecule
Reaction taking place Monomers join together by opening the C=C Loss of a small molecule each time a
bond monomer joins the chain
Only a single product Two products
Nature of product Non-biodegradable Can be biodegradable
Resistant to acids PET can be hydrolysed back to
monomers by acids or alkalis
Plastics
- polymers that can be moulded or shaped by the action of heat and pressure
Not all modern plastics are single-use and go straight to waste. PET can be used to make items such as soft-
drinks bottles and these can be re-used or recycled.
Disposal of plastic waste
✓ Incineration – burning of plastic waste
✓ Disposal in landfill – burrowing plastic waste
✓ Accumulation in oceans – discarding plastic waste into oceans
Many are non-biodegradable – cannot be broken down by micro-organisms.
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