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 ORGANIC MOLECULES
 Organic chemistry is the chemistry of carbon compounds in living and non-living systems.
 Organic compounds contain carbon and hydrogen atoms.
 These compounds can be in the gaseous, liquid, or solid phase.
 All living matter contains organic compounds.
 CARBON
 Carbon is very unique and is the basic building block of all organic compounds.
 It is atoms have a valency of four in a tetrahedral arrangement.
 This means it is able to make four bonds.
 Carbon atoms can form single, double or triple bonds
 Carbon atoms have to form 4 bonds, but not necessarily with 4 other atoms
 HYDROCARBONS
 A hydrocarbon is a compound that contains only carbon and hydrogen atoms.
 These compounds can be saturated (single bonds) and unsaturated (double or triple bonds).
 Hydrocarbon: A compound containing only carbon and hydrogen atoms.
 Saturated compound: A compound in which all of the bonds between carbon atoms are single
bonds.
 Unsaturated compound: A compound in which there is at least one double and/or triple bond
between carbon atoms.
 Alkane: An organic compound containing only C-H and C-C single bonds.
General formula: CnH2n + 2
 Alkene: A compound of carbon and hydrogen that contains a carbon-carbon double bond.
General formula: CnH2 n
 Alkyl group: A group formed by removing one H atom from an alkane.
 Alkyne: A compound of carbon and hydrogen that contains a carbon-carbon triple bond.
General formula: CnH2 n -2
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 ORGANIC COMPOUNDS
 Molecular formula: Does not show any bonds, only the number of each atom present in the
compound
 Condensed formula: This formula does not show all the bonds but shows the important bonds
and general structure.
 Macromolecule: A molecule that consists of a large number of atoms.
 Structural formula: A structural formula of a compound shows which atoms are attached to
which within the molecule. Atoms are represented by their chemical symbols and lines are used to
represent ALL the bonds that hold the atoms together.
 Substituent (branch): A group or branch attached to the longest continuous chain of C atoms in
an organic compound.
 ALCOHOL
 Alcohol: An organic compound in which H atoms in an alkane have been substituted with
hydroxyl groups (-OH groups).
 Are saturated and have a hydroxyl functional group.
 Are bonded by strong hydrogen bonds and by weak Van der Waals forces
 Are less polar as the number of C-atoms in the molecule increases;
 Are generally soluble in polar and in non-polar solvents;
 Are highly flammable and mostly liquids at room temperature.
General formula: CnH2n + 1OH
 Classification of alcohol
 Primary: One C bonded to the C - OH
 Secondary : Two C’s bonded to the C - OH
 Tertiary: Three C’s bonded to the C- OH
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 ISOMERS
 Isomers: Compounds having the same molecular formula but different structural formulae.
 Chain isomers: These have the same molecular formula but different chains
 Positional isomers: These have the same molecular formula but the functional group is in a
different position
 Functional isomers: These have the same molecular formula but a different functional group.
Aldehydes and ketone are functional isomers as well as carboxylic acids and esters
 Homologous series: A series of organic compounds that can be described by the same general
formula OR in which one member differs from the next with a CH2 group
 Functional group: A bond or an atom or a group of atoms that determine(s) the physical and
chemical properties of a group of organic compounds.
 Condensed structural formula: A formula that shows the way in which atoms are bonded together
in the molecule, but DOES NOT SHOW ALL bond lines.
 Functional group: A bond or an atom or a group of atoms that determine(s) the physical and
chemical properties of a group of organic compounds.
 Functional isomers: Compounds with the same molecular formula, but different functional groups.
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 ORGANIC FUNCTIONAL GROUPS
 ORGANIC CHEMISTRY- NOMENCLATURE
 Drawing of structural formulae of organic compounds
 All bonds must be shown as short vertical or horizontal line.
 No part of the structure should be condensed
 Even the bond between O and H must be shown i.e. -O-H not –OH.
 All H atoms should be shown around C atoms.
 Marks are deducted if only bonds shown and not the H atoms.
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 Writing of IUPAC names of organic compounds
 IUPAC name: A chemical nomenclature (set of rules) created and developed by the International
Union of Pure and Applied Chemistry (IUPAC) to generate systematic names for chemical
compounds.
 Hyphens are used between a word and a number e.g 2-methylbutane.
 Commas are used between numbers e.g. 2,3-dimethylbutane.
 Marks are deducted if hyphens and / or commas are omitted.
 Hyphens should NOT be used between words.
 All IUPAC names are written as one word, except esters and carboxylic acids.
 IUPAC NAMING AND FORMULAE
 Write down the IUPAC name when given the structural formula or condensed structural formula
for compounds from the homologous series above, restricted to one functional group per
compound, except for haloalkanes.
 For haloalkanes, maximum two functional groups per molecule.
 Write down the structural formula when given the IUPAC name for the above homologous series.
 EACH IUPAC NAME CONSISTS OF THREE PARTS:
 Prefix
: Position and names of substituents (side chains), listed alphabetically.
 Root
: Number of C-atoms in the main C-chain.
 Suffix
: Determined by the homologous series.
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KEY!
 CARBON ATOMS IN MAIN CHAIN VS ROOT NAME
1
→
meth−
2
→
eth−
3
→
prop−
4
→
but−
5
→
pent−
6
→
hex−
7
→
hept−
8
→
oct−
9
→
non−
10
→
dec−
 Number of substituents vs Substituent prefix
2
→
di
3
→
tri
4
→
tetra
 SUFFIX NAMES
Alkane
-ane
Alkene
-ene
Alkyne
-yne
Alcohol
-anol
Carboxylic acid
-anoic acid
Ester
-anoate
Aldehyde
-anal
Ketone
-anone
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 HALOALKANE
 Haloalkane (Alkyl halide): An organic compound in which one or more H atoms in an alkane
have been replaced with halogen atoms.
 Are alkanes with halogen (Br, Cℓor I) substituents;
 Are saturated and therefore relatively unreactive.
 Are bonded by weak Van der Waals intermolecular forces
 Are poisonous and mostly liquids at room temperature.
 The more halogen atoms on a haloalkane, the more poisonous the substance and
 Are the less flammable.
 General formula: CnH2 n + 1X (X = F, Cℓ, Br or I)
 X REPESENTS A HALOGEN:
o Fluorine
:
fluoro−
o Chlorine
:
chloro−
o Bromine
:
bromo−
o Iodine
:
iodo−
 ALDEHYDES
 Aldehydes: Organic compounds having the general structure RCHO where R = H or alkyl.
General formula: RCHO (R = alkyl group)
 Are functional isomers of the ketones;
 Are liquids at room temperature except for methanal which is gaseous.
 Are responsible for pleasant smells (long C-chain aldehydes) and odours (unpleasant smells) in
short chain aldehydes.
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 KETONES
 Carbonyl group: Functional group of ketones (> C = O)
 Are functional isomers of the aldehydes;
 Are liquids at room temperature;
 Are abundant in nature and often have pleasant scents (smell) and used to produce perfumes.
 CARBOXYLIC ACIDS
 Carboxyl group: Functional group of carboxylic acids (-COOH)
 Carboxylic acid: An organic compound containing a carboxyl group (-COOH group).
 General formula: CnH2 n + 1COOH (or RCOOH)
 Are functional isomers of the esters
 Are liquids at room temperature;
 Are weak acids and very polar molecules.
 ESTERS
 Are saturated molecules with an ester functional group.
 Are functional isomers of the carboxylic acids
 Are liquids at room temperature;
 Are produced when an alcohol reacts with a carboxylic acid
 Are responsible for pleasant smells (long C-chain esters) and volatile (evaporate easily).
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 ORGANIC CHEMISTRY- PROPERTIES
 Van der Waals forces: A combined name used for the different types of intermolecular forces.
 Vapour pressure: The pressure exerted by a vapour at equilibrium with its liquid in a closed
system.
 Boiling point: The temperature at which the vapour pressure of a liquid equals atmospheric
pressure.
 Melting point: The temperature at which the solid and liquid phases of a substance are at
equilibrium.
 Intermolecular force: Forces between molecules that determine physical properties of
compounds.
 Dipole-dipole force: Intermolecular forces found between polar molecules i.e. molecules in
which there is an uneven distribution of charge so that the molecule has a positive and a negative
side.
 London force: A weak intermolecular force between non-polar molecules.
 Hydrogen bond: A strong intermolecular force found between molecules in which an H atom is
covalently bonded to wither an N, O or F atom.
 Specify the type of van der Waals force and relate them with Boiling point, Melting point and
Vapour pressure.
 Describe the trend in the boiling points / Melting Point and Vapour pressure of the compounds.
 Give an explanation for the trend. In your explanation make reference to INTERMOLECULAR
FORCES and the ENERGY needed.
 THE BOILING POINT INCREASES:
As the molecular mass/size of the molecule increases.
As the Carbon chain/ surface area increases
The strength of the London/dipole-dipole forces increases.
Hence more energy is needed to overcome the Intermolecular forces.
Thus the boiling points/ Melting points increase but Vapour pressure.
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 STRONG VS WEAK INTERMOLECULAR FORCES
 NON – POLAR MOLECULES
 Weak Van Der Waals
 London / dispersion / induced dipole
 Weak forces: less energy needed to break bonds
 Lower boiling point/melting point
 High vapour pressure
 POLAR MOLECULES
 Strong Van Der Waals
 Dipole-dipole force
 More energy needed to break bonds
 High boiling point/melting point
 Lower vapour pressure
 ALCOHOL
 Strong hydrogen bond
 More energy needed to break bonds.
 High boiling point/melting point
 Lower vapour pressure
 Has one site of hydroxyl group.
 CARBOXYLIC ACIDS
 Strong hydrogen bond
 More energy needed to break bonds
 High boiling point/melting point
 Lower vapour pressure.
 Two site of hydroxyl group
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KEY!
VAN DER WAALS FORCES
 London forces
 Dipole-dipole
 very weak
 slightly stronger than
 found between non-polar
molecules
HYDROGEN BONDS
 strongest intermolecular
London forces
 found between slightly
force
 found in strongly polar
polar molecules
molecules
EXAMPLES
Alkanes
Aldehydes
Alcohols
Alkenes
Ketones
Carboxylic acids
Alkynes
Esters
Alkyl halides
WHEN ANSWERING A QUESTION RELATING TO INTERMOLECULAR FORCES, THE LEARNER MUST:
 Mention and specify the type of intermolecular force.
 Mention the amount of energy required to break the intermolecular forces.
 Mention the structure of the molecule.
 NUMBER OF FUNCTIONAL GROUPS
 An increase in functional groups increase the IMF:
o Increasing IMF
o More energy required to overcome the bonds
 CHAIN LENGTH: MOLECULAR MASS
 The greater the number of carbon atoms in the chain, the greater the molecular mass.
 An increase in molecular mass increases the IMF:
o Increasing IMF
o More energy required to overcome the bonds
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 CHAIN LENGTH: BRANCHES
 More branching results in a smaller surface area and lower the strength of the IMF:
o Decreasing IMF
o Less energy required to overcome the bonds
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 ORGANIC REACTIONS
 Addition reaction: A reaction in which a double bond in the starting material is broken and
elements are added to it.
 Halogenation: The reaction of a halogen (Br2, Cℓ2) with a compound.
 Substitution reaction: A reaction in which an atom or a group of atoms in a molecule is replaced
by another atom or group of atoms.
 Cracking: The chemical process in which longer chain hydrocarbon molecules are broken down
to shorter more useful molecules.
 Dehydration: Elimination of water from a compound usually such as an alcohol.
 Dehydrohalogenation: The elimination of hydrogen and a halogen from a haloalkane.
 Elimination reaction: A reaction in which elements of the starting material are “lost” and a
double bond is formed.
 Esterification: The preparation of an ester from the reaction of a carboxylic acid with an alcohol.
 Hydration: The addition of water to a compound.
 Hydrocarbon: Organic compounds that consist of hydrogen and carbon only.
 Hydrogenation: The addition of hydrogen to an alkene
 Hydrohalogenation: The addition of a hydrogen halide to an alkene.
 Hydrolysis: The reaction of a compound with water.
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A. ADDITION REACTIONS (UNSATURATED → SATURATED)
 Addition reactions are reactions where atoms are added to an organic molecule.
 The double or triple bonds break open and the new atoms are added to the carbon atoms on either
side of the double or triple bond
1. Hydrogenation – add H2
 Hydrogen + Alkene / Alkyne →
Alkane
 Reaction conditions: The alkene needs to be dissolved in a non-polar solvent and needs to have a
catalyst present eg. Pt, Ni or Pd
2. Halogenation – add X (X = Halogen: F2, Cl2, Br2, I2 )
 Halogen + Alkene / Alkyne →
Haloalkane
 Reaction conditions: No water to be present if it is to take place
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3. Hydrohalogenation – add HX (X = Halogen: F2, Cl2, Br2, I2)
 Hydrogen Halide + Alkene / Alkyne →
Haloalkane
 Reaction conditions: No water to be present if it is to take place.
 Markovnikov’s rule: The H atom will bond to the carbon atom which has the greater number
of H atoms bonded to it. (Form biggest H groups)
4. Hydration – add of H2O
 Water (H2O) + Alkene / Alkyne →
Alcohol
 Reaction conditions: Strong but dilute acid catalyst e.g. H2SO4 or H3 PO4.
 Heat in the form of steam (H2O) reactant.
 Markovnikov’s rule: The H atom will bond to the carbon atom which has the greater
number of H atoms bonded to it. (Form biggest H groups)
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B. ELIMINATION REACTIONS (SATURATED → UNSATURATED)
 An elimination reaction is a reaction where atoms or groups of atoms are removed from an
organic molecule to form either a double or triple bonded compound.
1. Dehydrogenation – remove H2
 Alkane
→
Alkene + Hydrogen
 Reaction conditions: The alkane needs to be in the presence of a catalyst eg. Pt, Ni or Pd
2. Dehalogenation – remove X (X = Halogen: F2, Cl2, Br2, I2)
 Haloalkane
→
Alkene + Halogen
 Reaction conditions: Takes place in an unreactive solvent
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3. Dehydrohalogenation – remove HX (X = Halogen: F2, Cl2, Br2, I2)
 Haloalkane
→ Hydrogen halide + Alkene
 Reaction conditions: Takes place in the presence of concentrated NaOH / KOH in ethanol as
the solvent. Heat
 Zaitzev’s rule: H atom is removed from the carbon atom with the least number of H atoms.
(Keeps biggest H groups)
4. Dehydration – remove H2O
 Alcohol
→ Water (H2O)
+
Alkene
 Reaction conditions: Requires the heating of an alcohol with concentrated acid catalyst eg.
H2SO4 or H3 PO4. The acid should be in excess.
 Sulphuric acid is known as a dehydrating agent.
 Zaitzev’s rule: H atom is removed from the carbon atom with the least number of H atoms.
(Keeps biggest H groups)
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C. SUBSTITUTION REACTIONS (SATURATED → SATURATED)
 Substitution reactions: is when an atom or group of atoms in an organic molecule are replaced or
swopped/exchanged for another atom or group of atoms.
 Substitution reactions take place between compounds that are saturated alkanes, haloalkanes and
alcohols.
1. Alkanes: Halogenation- Substitute X2 (X = Halogen: F2, Cl2, Br2, I2)
 Alkane
+ Halogen
→
Haloalkane + Hydrogen Halide
 Reaction conditions: Reaction takes place in the presence of sunlight/heat
2. Haloalkanes: Hydration- Substitute H2O
 Haloalkane + H2O/NaOH/KOH →
alcohol
+
HX / NaX / KX
 Reaction conditions: The haloalkane is dissolved in an ethanol solution and treated with hot
aqueous NaOH / KOH solution
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3. Alcohols: Hydrohalogenation- Substitute HX (X = Halogen: F2, Cl2, Br2, I2)
 Tertiary alcohol
 Alcohol + Hydrogen Halide →
Haloalkane + Water
 Reaction conditions: Require HX present at room temperature.
 Primary and secondary alcohol
 Alcohol + Hydrogen Halide →
Haloalkane + Water
 Reaction conditions: High temperatures and need to be treated with NaBr and concentrated
H2SO4.
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D. COMBUSTION REACTION
 Combustion reactions – These reactions involve the burning of hydrocarbons, alcohols and esters
in oxygen.
 These molecules are highly flammable.
 Hydrocarbons are the main source of fuel in the world at the moment.
 They are used in the production of electrical energy and as fuel for various engines.
 When hydrocarbons and alcohols react with oxygen they form water and carbon dioxide.
 These reactions are exothermic and produce large quantities of heat.
 COMPLETE COMBUSTION
EXCESS OXYGEN
RECTION:
C3 H8 + 5O2 → 3CO2 + 4H2O + energy
 INCOMPLETE COMBUSTION
INSUFFICIENT OXYGEN
 REACTION:
2C3 H8 + 7O2 → 6CO + 8H2O + energy
BALANCING: C → H → O
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E. CRACKING
 Hydrocarbons can be made up of very long chains of hundreds of carbons.
 Crude oil is a mixture of many large hydrocarbons and each source of crude oil is different
resulting in different types and amounts of hydrocarbons.
 Shorter chain hydrocarbons are more useful to use as fuels as they burn more readily and are
more flammable.
 Cracking is the breaking up of long hydrocarbon chains into smaller more useful
hydrocarbons. An alkene and alkane will be the products as a result of cracking.
 Cracking is a type of elimination reaction.
1. THERMAL CRACKING
 This method makes use of high pressures and high temperatures to crack the long
hydrocarbon chains with no catalyst.
2. CATALYTIC CRACKING
 This method uses a catalyst to crack long carbon chains at low pressure and low temperature.
 The heated crude oil is passed into a fractional distillation column and passed over a catalyst.
 The column is hottest at the bottom and coolest at the top.
 The crude oil separates according to boiling points and condenses as the gas rises up the
column.
 The substances/chains with the longest chains will have higher boiling points and condense at
the bottom and vice versa.
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F. ESTERIFICATION
 This is a reaction between an alcohol and a carboxylic acid in the presence of a concentrated
acid catalyst, H2SO4.
 alcohol + carboxylic acid → ester + water
 This reaction is a type of an elimination reaction and is also known as a condensation reaction as
two organic molecules form one organic molecule.
 And water is removed from the reactants and forms as a product in the reaction.
 Esters are responsible for the various smells which occur in nature and they are generally pleasant
smells like banana and apple etc.
KEY!
 HYDROLYSIS
 It is a substitution reaction.
 Product is alcohol.
Reaction conditions:
 NaOH and water
 Solution heated mildly
 HYDRATION
 It is an addition reaction.
 Product is alcohol.
Reaction condition:
 Conc. H2SO4 (catalyst) and water added
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G. POLYMERS
 Polymers are very large organic molecules.
 They are made up of hundreds or thousands of atoms.
 Polymers are structured from repeated smaller units called monomers.
 Monomer: Small organic molecules that can be covalently bonded to each other in a repeating
pattern
 Polymer: A large molecule composed of smaller monomer units covalently bonded to each
other in a repeating pattern.
 Polymerisation: A chemical reaction in which monomer molecules join to form a polymer
 Addition polymer: A polymer formed when monomers (usually containing a double bond)
combine through an addition reaction.
 Addition polymerisation: A reaction in which small molecules join to form very large
molecules by adding on double bonds.
 Condensation polymer: A polymer formed by two monomers with different functional
groups that are linked together in a condensation reaction in which a small molecule, usually
water, is lost.
 Condensation polymerisation: Molecules of two monomers with different functional groups
undergo condensation reactions with the loss of small molecules, usually water.
 CONDENSATION POLYMERIZATION
 Occurs when two different monomers which have functional groups (alcohols and carboxylic
acids) on both ends of their molecules react.
 In this reaction a water molecule is eliminated.
 ADDITION POLYMERS
 Are made by joining two or more monomers which have double bonds- unsaturated molecules.
(These are alkene’s and alkyne’s) and form long single bonded chains.
 The double bond breaks open and the electrons join the two monomers together to create the long
chain.
 No atoms are added or lost. Monomers may have different groups that are attached to the carbon
atoms.
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 IDENTIFYING THE TYPE OF POLYMERISATION
 it involves three simple steps, and show the learners with suitable example how these steps are
undertaken:
o Recognise the repeating unit and place a bracket around it.
o Look at the repeating unit and see it there are any carbonyl (=O) or hydroxyl (-OH) groups on the
unit. If there are none, then we have identified an addition polymer.
o If there are carbonyl or hydroxyl groups on the repeating unit, then we have identified a
condensation polymer.
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MEMO: 02
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MEMO: 03
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