ORGANIC CHEMISTRY

Reference is made to text or sketches from:

Du Plessis, D. et al. Solutions for all, Learner’s book 12, MacMillan, Gauteng, 2013.
Olivier, A. Physical Sciences Book 2 Grade 12, Reivilo Publishers, Kroondal.
http://www.foresight.org/conferences/MNT7/Papers/Hersam/Fig3.gif
ORGANIC MOLECULES: General information

• Organic chemistry refers to the chemistry of CARBON

compounds
• Carbon is the basic building blocks of organic compounds
• Together with hydrogen they form hydrocarbons

-
• Consider the Aufbau Diagram of Carbon

Ground state Excited state

• The carbon atom can form a maximum of 4 covalent bonds in the excited
state (4 half-filled orbitals that can overlap with H)
• It can bond to other carbon atoms, to form single, double or triple bonds
• Can bond to other carbon atoms to form long chains
• Can also form branches (substituent groups) or ring structures
• Can bond with other atoms (e.g. hydrogen, oxygen, halogens, etc.)
Classification of organic compounds
Representing organic molecules

Different types of formulas can be used to represent organic molecules:

• Molecular formula: A chemical formula that indicates the type of atoms

and the correct number of each in a molecule, e.g. C4H10 (Butane)
• 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 (Couper).

• Condensed structural formula: This notation shows the way in which

atoms are bonded together in the molecule, but DOES NOT SHOW ALL
bond lines.
e.g. CH3CH2CH2CH3 (Butane), or
Hydrocarbon: Organic compounds that consist of hydrogen
and carbon only.
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 .
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.

• Compounds in a homologous series have the same

functional group and can be described using the same
general formula. (E.g. Alkanes CnH2n+2)

C4H2(4)+2 = C4H10
(see page of all functional groups)
Functional group structures
Alkanes
• SATURATED hydrocarbons (only contain SINGLE bonded carbon
atoms)

• Homologous series: Cn H2n+2

• Naming Alkanes…
• The following prefixes are used to Number of Carbons Root name
indicate the number of carbons
1 Meth -
present in the molecule:
2 Eth -
3 Prop -
4 But -
5 Pent -

Butane 6 Hex -
7 Hept -
8 Oct -
• Some molecules contain branches (where a hydrogen has been
replaced with carbon chains – substituent groups)

2-methylpropane

• (REMEMBER: same molecular formula as pentane: C5H12 – they are

CHAIN ISOMERS)
• The substituent carbon chain (side chain) is called an ALKYL group
• These alkyl groups are named as follows:

Alkyl group Name

CH3- Methyl -

CH2CH3- Ethyl -

CH2CH2CH3- Propyl -

CH2CH2CH2CH3- Butyl -
Procedure for naming the alkanes:
1. Find the LONGEST continuous carbon chain in the molecule (parent
chain)
2. Identify the attached alkyl groups
3. To indicate the positions of the branches, number the carbon atoms
in the longest chain, starting from the side closest to a branch!
4. If two of the same branch occurs, position of each is given as well as
di-, tri-, tetra-, etc.
5. To write down the name, start by writing down the name of the main
chain, then, in front of that …
6. the position and name of all the attached groups in alphabetical order
(if there is more than 1 of a particular alkyl group, use the prefixes:
mono, di, tri and tetra to indicate the number of groups – DO NOT
consider prefixes for alphabetical ordering)
Note: the name is written as 1 WORD, with numbers and words separated
by dashes and numbers separated by commas, e.g.
4-ethyl-2,3-dimethylheptane (no spaces)
See worked examples on p. 90
Homework: p. 94
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Note:
• the name is written as 1 WORD,
• with numbers and words separated by dashes and
• numbers separated by commas,
• e.g.
3-ethyl-4,3-dimethyloctane (no spaces)
Draw this structure:

See worked examples on p. 90

Homework: p. 94
Alkenes (p. 95)
• UNSATURATED hydrocarbons: Compounds with one or more multiple
bonds between C atoms in their hydrocarbon chains.
(two hydrogen atoms removed from the alkane, the electrons
‘moved’ in-between the C atoms)

• The double bond is a centre of high reactivity (high electron density)

• Homologous series with general formula: Cn H2n
• The simplest alkene is ethene…

• See more examples on p. 95

Procedure for naming alkenes:
1. Find the longest chain containing the double bond (parent
chain)
2. Add the suffix “ene” to the parent chain
3. Number the chain starting from the end closest to the
double bond
4. The position of the double bond is indicated by the number
on the first carbon atom of the double bond
5. When the root chain contains branched substituents, the
same rules used for naming alkanes is followed

3,3-dimethylbut-1-ene
Branched alkenes:
Number the chain starting from the end closest to the double
bond, NOT the branch

3-methylbut-1-ene

Remember: the double bond is a functional group. IT MUST be

included in the longest continuous chain
Comparative reactivity of alkenes and alkanes
• Alkenes are MUCH more reactive than Alkanes
• Alkenes are unsaturated (they have a reactive double
bond)

Reactive double bond present No double bond present

• This means they can readily react

Alkynes (p. 98)
• UNSATURATED hydrocarbons (covalent TRIPLE bonds
between carbon atoms – another 2 hydrogens removed,
and the electrons moved in-between the C atoms)

• The triple bond is a centre of high reactivity (high electron

density)
• Homologous series: CnH2n-2
Procedure for naming:
The same rules apply as for the naming of alkenes,
but the suffix -yne is used.

Homework: do Exercise 3.2 on p.100

Homework space:
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Alkyl halides (p. 100)

• Alkane where one of the hydrogen atoms has been

replaced with a halogen

• Homologous series: CnH2n+1X (where: X = F, Cl, I, Br)

HALIDE ATOM PREFIX

F fluoro -
Cl chloro-
Br bromo-
I iodo-
Procedure for naming alkyl halides:

2-chloropentane

1. Determine the length of longest chain (root name)

2. Start numbering from the side closest to the first substituent
regardless of what it is
3. If more than one type of halogen present, indicate the number using
di, tri or tetra
4. If there are two different types of halogens in the molecule, each one
present must receive its own number and be arranged in alphabetical
order
5. Should the numbering of the root chain, from both sides, give the
same smallest number, alphabetical preference is given to the one
side
6. When both halide and alkyl groups are present, numbering starts
nearest to the first substituent, NOT closest to the halide (Cl, Br, I, F)
7. Do more examples: see p. 101
p.101 examples
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 https://chemlaba.wordpress.com/2011/03/12/iupac-nomenclature-of-alkyl-halides/

If the same numbers apply in numbering, the alphabetic rule

takes preference:
2-methyl-6-chloroheptane
OR
2-chloro-6-methylheptane

THUS, correct one is:

2-chloro-6-methylheptane
Aldehydes and Ketones
• Aldehydes and ketones are compounds that have a CARBONYL group
• A carbonyl group is a group containing an oxygen atom that is bonded
with a double bond to a carbon atom

Aldehydes
• contains a carbonyl group attached to end of a chain
(with at least one H-atom attached to it)

• Functional group: Formyl group

• Another way of writing it: (where R = any part of a

C chain)
 Naming aldehydes
• Identify the longest chain of C atoms, including the C in the
carbonyl group
• Numbering begins at the C in the carbonyl group
• Aldehyde names end with “-al”

(Formaldehyde)

• See more examples on p.102 (Science around us)

Ketones
Contains a CARBONYL group that is bonded somewhere in the middle
of a chain (NOT at the end) – it is bonded to 2 carbon atoms

Naming ketones
• Ketone names end with “-one”
• The root name must contain the carbonyl group
• Numbering begins at the end closest to the carbonyl group
Alcohols
• Homologous series: CnH2n+1OH
• Shortened notation: R-OH __
• (R = any carbon chain)

Methanol: used in methylated spirits (for general use

that has been made unfit for drinking by
the addition of some pyridine and a violet
dye)
Ethanol: alcoholic drinks – very poisonous
fuel in cars (produced from sugar cane)
Naming compounds containing alcohol group
• Identify the longest chain of C atoms, and write it with the suffix “-ol”
• The position of the “-O-H” group (hydroxyl) is indicated according to
the regular numbering system used with molecules containing other
functional groups
• Compounds that contain more than one “-O-H” group, are called
(diols, triols, etc.)
But… is an alcohol molecule polar or non-polar?
• It depends on the size of the non-polar alkyl group
• The larger the alkyl group gets, the more significant it
becomes in the molecule and thus the compound
becomes less soluble in water (i.e.: more non-polar.
Remember water is polar.)
• Rule: when there are 4 or more carbon atoms in the
dominant part of the molecule, the molecule is considered
non-polar (thus insoluble in water)
• But…
• alcohols with branched alkyl groups are more soluble in
water than those without branches, because the branch
decreases the contact surface area of the non-polar part
of the molecule – the molecule is more spherical
PRIMARY alcohols
• O-H group is on the end of the longest carbon chain
• The C with the O-H group has two H atoms

Secondary alcohols
• O-H group is not at the end of the chain
• the carbon atom with the O-H group has one H atom and
two carbons chains (can be same or different lengths)
Tertiary alcohols
• O-H group is (again) not at the end of the chain
• the carbon atom with the O-H group is attached to three C
atoms which is part of the carbon chain (with different
lengths or different carbon groups)

• Homework: p. 106 (Checkpoint 11)

• Homework: p. 106 (Checkpoint 11)
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Carboxylic acids
• A carboxylic acid contains a carboxylic group, -COOH
(carboxyl = carbonyl + hydroxyl)
• General formula: CnH2n+1COOH
Naming carboxylic acids

•Identify the longest chain that contains the carboxyl group

•Carboxylic acid names end in “-oic acids”
•The root chain must contain the carboxylic group (numbering
starts here)
•Number substituents according to position and arrange
alphabetically
Esters (p. 110)
Properties
• Pleasant smell or odour – they occur naturally in fruits
• Chemically prepared for use in perfumes
• Esters are derived from alcohols and carboxylic acids
• They contain a carboxylic group of which the hydrogen atom (of
the hydroxyl group) has been replaced by an alkyl group (R’)
Esterification
Esters form when an alcohol and a carboxylic acid react (catalyst - H2SO4)

Catalyst H2SO4

Condensation (water forms)

• Reaction conditions: added catalyst (sulphuric acid) and mild heating

• H2SO4 is a catalyst and a dehydrating agent (removes H2O)

(All learners will do esterification as a prescribed departmental practical)

Naming of Esters

• Name the alcohol part first, according to the number of C-atoms

(methanol changes to methyl)
• Then name the acid part according to the number of C-atoms
• (ethanoic acid changes to ethanoate)
• Thus… methylethanoate
• When there are substituents present – they get the
number of the carbon atom to which they are bonded
(numbering starts at C-atom closest to carbonyl group)
• Substituents on the alcohol part are the prefixes for the
alcohol part of the name, while the substituents on the
carboxyl part are the prefixes for the carboxyl part of the
name!
Isomers (p.110)
• Molecules that have the same molecular formula, but different
structural formulae
•Chain isomerism (branching occurs): Same molecular formula, but
different types of chains, e.g.
•

• See worked examples on p. 111

Isomers (p.110) - continue

•Position isomerism (functional groups are in different positions):

Same molecular formula, but different positions of the side chain,
substituents or functional groups on the parent chain, e.g. 1-choropropane
and 2-chloropropane or but-2-ene and but-1-ene
Isomers (p.110) - continue
•Functional group isomerism: Same molecular formula, but different
functional groups, e.g. methyl methanoate and ethanoic acid.
• Thus different homologous series
• E.g. esters and acids, and aldehyde and ketone
• Do p. 112 Ex 3.7
Homework p. 112 Ex 3.7
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Intermolecular (IM) forces: revision of gr.11 work

• Van der Waals’ forces and Hydrogen bonds

(remember Hydrogen bonding is a special type of dipole-dipole force)
• When answering melting/boiling point questions, always use these 4
steps:
1. Identify the IM forces 
2. Compare the strength of forces 
3. Mention that more energy is needed to break stronger bonds 
4. Mention that a higher temperature is reached for more energy
needed 
Consider the two types of Van der Waals’ forces…
Van der Waals’ dispersion (or London) forces
• When 2 NON-polar molecules approach each other, attraction as well as
repulsion, between the nuclei can cause an unequal distribution of charge
• This causes, TEMPORARY dipoles to be produced
• These temporary dipoles induce temporary dipoles in adjacent
molecules
• This results in a weak force of attraction between molecules

Van der Waals dipole-dipole forces

• When atoms of different electronegativities bond with each other to form a
molecule, the molecule that is formed has an unequal distribution of
charge
• This unsymmetrical charge distribution results in the formation of a
POLAR molecule (dipoles – one side slightly negative, the other slightly
positive)
• When polar molecules are close together they exert forces on each other
• H-bonding is a special type of Dipole-diploe force
 Summary and comparison of forces (p. 113)

Van der Waals’ forces Hydrogen bonds

London forces (Induced dipole) Dipole-dipole
Intermolecular (IM) forces
Intermolecular forces influence the physical properties:
• Stronger IM forces mean molecules are not separating easily
• The longer a carbon chain, the higher the molecular mass, the stronger the IM
forces
• Branched molecules are more spherical (not straight chains, looks like a ‘ball’)
and therefore the IM forces are weaker
• The type of functional group influences the polarity, e.g.

• Remember that Hydrogen bonds form between an H on one molecule and the O
on another molecule

(2 sites for H-bonding)

Structural and physical properties (continue)

• Vapour pressure and Volatility

• Vapour pressure refers to the pressure caused by the vapour
formed above the liquid in a closed container
• Volatility is the measure at which a liquid changes to a vapour
(fumes that can be smelt)
• Volatility decreases as size of molecule increases (stronger forces,
less volatile. Molecules stay in liquid phase if forces are stronger)
• Thus, less volatile, less vapour pressure
• Viscosity
• Viscosity refers to the degree of fluidity (or flow) of a liquid
• Viscosity increases with intermolecular force strength
• (Viscosity increases with chain length – long chains get entangled)
(high viscosity = slow flow)
• Solubility
• The ability to dissolve in another substance (solvent)
- remember “like-dissolves-like”
• Alkanes are non-polar, thus they will dissolve in non-polar solvents
(e.g. organic solvents, and not in a polar solvent such as water)
• Melting and boiling points

• Consider the table of melting and boiling points:

• Van der Waals’ forces (intermolecular forces) increase as the
molecule size increases.
• The stronger the forces, the more energy is required to break the
forces, resulting in a higher boiling point
• Similarly with melting points, as the size of the molecule increases,
so does melting point
• The higher the boiling point the lower the vapour pressure.
• Why? _________________________________________________
________________________________________________________
Structural and physical properties of alkyl halides and alcohols

1) Higher melting points and boiling points than alkanes

with the same number of carbon atoms…
- alkane molecules, there are only ______________________forces
involved
- with alkyl halides and alcohols there are _________________________
forces involved
- the dipole-dipole forces are ________________ , thus more energy is
needed to separate the molecules

2) Melting points and boiling points _______________ as the number of

carbon atoms increase in the molecule…
- As before, the greater the molecular mass of the molecules, the
_____________ the forces involved

3) Increase in the number of branches and unsaturated bonds - MP and

BP __________________ .
(molecule becomes more spherical and thus reduces the surface area)
Physical properties of aldehydes and ketones
• Aldehyde and ketone molecules CANNOT form hydrogen bonds
between their own molecules, because the O is NOT bonded to an
H in the molecule
• So, it is expected that their boiling points will be lower compared to
the corresponding alcohols
• Aldehydes and ketones are polar molecules, because of the polar
carbonyl functional group. Therefore, Van der Waals’
______________ (type) forces can exist between molecules.
These forces are the reason that aldehydes and ketones have
_________ boiling points than non-polar alkenes
• Aldehydes and ketones can form hydrogen bonds with water!
• Thus they are soluble in water to a point. As with alcohols, the
small molecules are soluble, but as the size of the alkyl group
increases, the more insoluble they become (because the bigger
molecules become more non-polar – longer non-polar side to the
molecule)
Physical properties of alcohols
• Alcohols have a polar O-H group as well as a non-polar
hydrocarbon part
• Thus we have two types of bonding present:
1) Hydrogen bonding (between O-H groups)
2) Van der Waals’ forces (between alkyl groups)

Van der Waals H-bonding

Boiling and melting points
• Consider the table of boiling points

• The presence of strong hydrogen bonding between alcohol molecules

_________ the boiling points of alcohols (compared to alkanes – Van
der Waals’ forces)
• It can also be seen that the boiling points of the alcohols _________
as the number of carbon atoms in the molecule increases – this is due
to Van der Waals’ forces
Physical properties of carboxylic acids

• Very polar molecules (because the functional group is made

up of two polar groups)
• i.e. The hydroxyl group (-OH) and carbonyl group (C=O)
• The carboxylic acid molecules can form bonds with water
and other carboxylic acids
 Boiling points of carboxylic acids
• Carboxylic acids have _________ boiling points than ketones and
aldehydes (Why? ______________________________________
____________________________________________________)
• Carboxylic acids also have higher boiling points than alcohols.
• This is due to the fact that 2 hydrogen bonds form between 2
carboxylic acid molecules, compared to the 1 H-bond between 2
alcohol molecules

Carboxylic acid: 2 H-bonds

Alcohol: 1 H-bond
Solubility of carboxylic acids
- Due to the (very) polar nature of carboxylic acids, they are
__________ in water (like-dissolves-like)
- the solubility decreases as the size of the molecule increases
- Molecules with…
- Up to 4 carbons = very soluble (very polar)
- Up to 10 carbons = slightly soluble (less polar, greater
non-polar side with Van der Waals’
forces)
- More than 10 = insoluble
• Chemical properties
- Carboxylic acids are weak acids (e.g. vinegar) and thus only
partially ionise in water

CH3COOH + H2O  H3O+ + CH3COO-

• Boiling points of esters
- Do not form hydrogen bonds (since H is not bonded to O)
- Do form Van der Waals’ dipole-dipole forces
- Thus have boiling points similar to aldehydes and ketones
- Esters are less polar than alcohols.
- Consequently, esters are more volatile than carboxylic acids of
similar molecular weight
• Solubility (rule: ”like-dissolves-like”)
- Do form H-bonds with water
- Small esters are soluble in water (dipole-dipole)
- But larger ones are insoluble
-
Reactions of organic
molecules
Combustion (oxidation)
• Reaction of organic compounds with oxygen
• Always forms H2O and CO2 (with insufficient O2, poisonous CO forms)
• In the presence of sufficient oxygen…
CH4 + O2 CO2 + H2O
Tip: Always balance the atom which appears in a diatomic molecule (O2), last.
1. Balance C and H
CH4 + O2 CO2 + 2H2O
2. Balance the O by dividing the total on the right by 2 (4÷2 = 2)
CH4 + 2O2 CO2 + 2H2O

Note: - Alkanes are our most important fuels (fossil fuels)

- Combustion of alkanes (oxidation) is HIGHLY EXOTHERMIC and
produces carbon dioxide and water as products (along with energy)

ALKANE + O2  H2O + CO2 + ENERGY ∆H < 0

Combustion (oxidation)
Another example: Combustion of propane
C3H8 + O2 CO2 + H2O
1. Balance C and H first
C3H8 + O2 3CO2 + 4H2O
2. Balance the O by dividing the total on the right by 2 (10÷2 = 5)
C3H8 + 5O2 3CO2 + 4H2O
• Substitution (halogenation) – p. 128
• Replacing an atom or group of atoms with another atom or group of
atoms
• Takes place in saturated compounds (alkanes, haloalkanes, alcohols)
• Know about: Primary carbon, Secondary carbon, Tertiary carbon

C bonded to 1 C bonded to 2 C bonded to 3

carbon carbons carbons

See p. 128 Fig 3.48

Substitution (halogenation) – p. 128
• Alkanes react with halogens (F2, Cl2, Br2) when heated or in the
presence of light
• Heat indicated with Δ and light indicated by hf

• Examples: methane reacting with chlorine

Ethane reacting with bromine

• Substitution in alkanes occurs when one or more hydrogen atoms

in an alkane molecule are substituted by another atom or group
of atoms.
• See p. 129 (Worked examples)

•Note: the product that is formed is known as an alkyl halide or

haloalkane
The reaction is often difficult to control, and further substitution
can occur, replacing all the hydrogen atoms with halogen atoms
Substitution between alcohols and haloalkanes– p. 130
• Interconversion takes place: alcohols haloalkanes
HX (acidic) + alcohol haloalkane
• Tertiary alcohols + HBr or HCl (At room temperature)
• Primary and secondary alcohols need high temperatures
(slow reaction)
• See p. 130 (Worked examples)
Bases + haloalkane alcohols
• Base is first dissolved in ethanol and heated
(alkyl halides do not mix with water, so before treating them with the
strong base (KOH or NaOH), they must be mixed in ethanol)
• Hot ethanolic NaOH or KOH + haloalkane
• See p. 131 (Worked examples)
Substitution reactions with alkyl halides
•Alkyl halides are easily converted to other functional groups

•Substitution reaction with potassium/sodium hydroxide (alcohol formation)

- Alkyl halides do not mix with water, so before treating them with
the strong base (KOH or NaOH), they must be mixed in ethanol
• Substitution with water - hydrolysis (alcohol formation)
• The reaction of a compound with water

• Alkyl halides do not mix with water, therefore they must be mixed in
ethanol
Addition reactions of the alkenes
• An addition reaction is a chemical reaction where a molecule attaches to
a double or triple bond of a second molecule to form a single molecule.
• Industrial production of: 1. Polyethylene (bottles and clingwrap)
2. Polyvinyl chloride (PVC) (plastic piping)
• During the reaction the multiple bond is broken and new atoms are
added to the molecule to form a more saturated product
• Examples of addition reactions…
1) Hydrogenation (adding two hydrogen atoms)

• The catalyst (Pt, Ni, Pd) lowers the activation energy of the reaction by
providing an area where the reactants can come into closer contact with
one another
2) Halogenation (adding two halogen atoms) – at room temperature

• Note: TEST FOR SATURATION: halogenation reaction where Br2 is added

to test for unsaturated hydrocarbons (demonstration by teacher)

• A solution containing an unsaturated hydrocarbon will discolour with the

addition of bromine water (the solution changes from orange-brown to
colourless)
• See p. 133 (Worked examples)
 3) Hydrohalogenation (addition of HX to alkenes)
• NO water present!

• Note: Markovnikov’s rule … (“the rich gets richer”)

• When a polar molecule (e.g. H-F, H-Cl, H-Br, H-I, H-OH) is
added to a hydrocarbon double bond, the hydrogen atom is
added to the carbon atom with the most H-atoms

Main product
(2-bromopropane)

Byproduct
4) Hydration (addition of water to alkenes)
• In the presence of a dilute acidic catalyst (H2SO4)
• Water is added to an alkene to form an alcohol
• One of the hydrogen atoms in the water molecule (H-OH) will bond to the
carbon atom of the double bond (obeying the Markovnikov’s rule)

• Now do: 1. Hydration of 2-methylpropene and

2. Hydration of 3-methylhex-1-ene

Addition reaction in industry p. 136

Elimination reactions with alkyl halides – p. 138
• Elimination reactions involve the removal of a smaller molecule out
of a larger molecule. .
1) Dehydrohalogenation
• During an elimination reaction of alkyl halides, the halogen atom
and the hydrogen atom of the adjacent carbon atom are removed
from the molecule

Reaction conditions: 1. Hot ethanolic NaOH or KOH

2. Reflux – the hot vapours condense and
return to the reaction vessel

See p. 139 (Worked examples)

• Another example of an elimination reactions with alkyl halides
(more than one product is possible)

but-2-ene (main product)

but-1-ene (byproduct)

Zeitzev’s rule: (Applied when one product is more favoured than the
other)
“If more than one product is possible during elimination, the main
product will be the alkene with the highest substituted double
bond” . (i.e. the highest number in the name)
“The poor gets poorer”: the hydrogen atom is removed from the
carbon atom with the least H-atoms, to form the double bond.
2) Elimination reactions: Dehydration of alcohols
• Water is eliminated from alcohol
• Reaction conditions: 1. Heat
2. Excess concentrated H2SO4 or H3PO4

• The alcohol loses the –OH group and an –H atom from the
adjacent carbon to form an alkene

Conc.
3) Elimination reactions (CRACKING of alkanes)
• The chemical process in which longer chain hydrocarbon
molecules are broken down to shorter more useful molecules.

Pt
C8H18 4 CH2 = CH2
800 oC
+ H2

• Depending on the length of the chain, multiple cracking

sequences can occur
• Consider the cracking of butane (3 possible products)
• Not all products will produce the same yield
• See examples on p.141
Revision/summary: How to form alcohols…
• Hydrolysis (Substitution with water)

• Hydration (Addition of water)

• Substitution (with a strong hot ethanolic base)

 Plastics and polymers (p.143)

Describe the following terms:

• Macromolecule: A molecule that consists of a large number of atoms
• Polymer: A large molecule composed of smaller monomer units
covalently bonded to each other in a repeating pattern
• Monomer: Small organic molecules that can be covalently bonded to
each other in a repeating pattern

• Polymerisation: A chemical reaction in which monomer molecules join

to form a polymer
Types of polymerisations

Addition and condensation polymerisation

• The type of polymerisation that occurs depends on the functional

group of the monomers
• Addition polymerisation: A reaction in which small molecules
join to form very large molecules by adding on double bonds
• Thousands of unsaturated molecules join together to form a
single product molecule

• Addition polymer: A polymer formed when monomers (usually

containing a double bond) combine through an addition reaction
• Equation for the polymerisation of ethene to produce polythene.
E.g.: Formation of polyethene (Polyethylene)
• Cheap plastic
• Used to make plastic bags, cling wrap,
plastic bottles and bullet proof vests
• Formed by the addition reaction of ethene
monomers to form the polymer: Polyethene
• Requires high temperatures and very high
pressures
• Double bond breaks
(creating two FREE RADICALS)
• Free radical = A molecular fragment having
1 or more UNPAIRED ELECTRONS
• The reaction equation:

• The above shows a single unit of the polymer

• The “n” indicates that the unit is repeated a number
of times
Identification of monomers from a polymer
(Given the structural formula of an addition polymer)
Follow these steps:
Step 1: Find a repeating unit and place a bracket around it (from the centre of
the molecule)

Step 2: Separate the repeating unit and insert a double bond between the
carbons

Step 3: Name or/and draw the monomer: Chloroethene

2) Condensation polymerisation (they contain = O or – O – groups)
• Molecules of 2 or more monomers, with different functional groups, undergo
condensation reactions (elimination-type reactions) with the loss of a small
molecule (usually water)
• Condensation polymer: A polymer formed by 2 monomers, with different
structural groups, that are linked together in a condensation reaction in which
a small molecule, usually water, is lost.
• Slower than addition polymerisation
• Contains alcohol and carboxylic acid functional groups
Difference between addition and condensation
polymerisation
• Condensation polymers are formed more slowly than addition
polymers
• Water is formed in condensation polymerisation and no by-
products are formed during addition (similar to esterification
reaction)
• Monomers of addition polymers contain carbon-carbon double
bonds (i.e. unsaturated molecules)
• Monomers of condensation polymers contain functional groups,
e.g. C = O group
• Hydroxyl group reacts with the Carboxyl group – water is
removed – molecules linked (form the C – O – C group)
• Work through the examples on p.145, 146,151.
 • Summary p. 163 and 164 NB!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
• Good luck for the exams!
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