ORGANIC CHEMISTRY INDEX

1. Naming and Formulae of Molecules

Notes Page 2 - 19

Activities Page 20 - 23

Past Matric Papers Page 24 - 30

Activities Memorandum Page 31 - 36

Past Papers Memorandum Page 37 - 41

2. Structure and Physical Properties

Notes Page 42 - 53

Activities Page 54 - 57

Past Matric Papers Page 58 - 61

Activities Memorandum Page 62 - 64

Past Papers Memorandum Page 65 - 67

3. Chemical Reactions

Notes Page 68 - 79

Activities Page 80 - 82

Past Matric Papers Page 83 - 89

Activities Memorandum Page 90 - 92

Past Papers Memorandum Page 93 - 99

4. Plastics and Polymers

Notes Page 100 - 103

Activities Page 104 - 104

Past Matric Papers Page 105 - 105

Activities Memorandum Page 106 - 106

Past Papers Memorandum Page 107 - 107

Graduation

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 1 of 107
 TOPIC : Organic ( or Carbon ) Molecules - Naming and Formulae
Organic molecules are molecules containing carbon atoms. ( Definition )
Carbon has amazing abilities to form bonds. It makes up all living things and millions of chemicals. Four examples:

food plastic chair petrol oil

Carbon is the basic building block of organic compounds that recycles through the Earth’s air, water, soil and living
organisms including human beings.
Carbon atoms have four valence electrons that form four bonds. So C has a valency of four.
•
We represent a carbon atom as C or • C • or C or
•
The simplest carbon compounds are hydrocarbons.
Hydrocarbons are organic compounds that consist of hydrogen and carbon only. ( Definition )
A hydrogen atom has one electron ( H • ) and can only form a single bond H‒ or

methane
H H
• •
CH4 H• C •H H C H
• •
• •
H H
molecular formula Lewis dot notation structural formula ball-and-stick model 3-D model
To help our understanding let us also picture a carbon
atom as if it were a person. This is just an analogy. C

When a match burns, all the elements that are in

the wood escape as gases and these gases bur n
just above the surface of the wood.
However, most of the carbon atoms just stick
together and remain after the other elements have
left, and so form the charred remains of the match.
So carbon is an exception because
carbon atoms naturally stick together.

The trees on the right are badly bur ned but their
carbon atoms remained so firmly bonded together
Wooden match burning. that the dead trees still have their original shape.
Consider the carbon atoms in hydrocarbons as they join together.
Hydrocarbons only have C and H atoms. structural formula
H H
C C
ethane C 2H 6 H C C H
molecular formula H H
CH3CH3
In a handshake, two hands form a single bond
condensed structural formula

Saturated compounds are compounds in which there are no multiple bonds between C atoms in their
hydrocarbon chains.
When there are only single bonds we say that the hydrocarbon is saturated.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 2 of 107
 Organic Molecules - Naming and Formulae NOTES
We can now make our first series of hydrocarbons. If only single bonds are involved, we call them alkanes.
( The “men” are just "pictures" to guide your thinking. The formulae are more accurate representations )
Alkane series General formula : Cn H2n + 2 structural formula
H
methane C CH4 H C H

H
ethane H H
C C molecular formula C 2H 6
H C C H
H H
CH3CH3

propane H H H
C C C C 3H 8
H C C C H
H H H
condensed structural formula C H C H C H
3 2 3

H H H H
butane C C C C C 4 H 10 H C C C C H
H H H H
C H 3 (C H 2) 2 C H 3
burning gas

The first four molecules are gases. We burn them as fuel.

Each member has a CH2 added on to the previous member.
The alkane functional group is a single bond.in a hydrocarbon.
Alkanes have only C ‒ H and C ‒ C single bonds.
Normal alkanes or n-alkanes are the normal or unbranched or straight chain alkanes.

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. ( Definition)
H H H H H liquid H H H H H H
pentane
H C C C C C H H C C C C C C H
H H H H H H H H H H H
pentane C 5 H 12 C H 3 (C H 2) 3 C H 3 hexane C 6 H 14 C H 3 (C H 2) 4C H 3

Condensed structural formula notation shows the way in which atoms are bonded together in a
molecule but does not show all bond lines. (Definition)

Molecular formula is a chemical formula that indicates the type of atoms and the correct number of
each in a molecule. (Definition)

H H H H H H H H H H H H H H H
H C C C C C C C H H C C C C C C C C H
H H H H H H H H H H H H H H H
heptane C 7 H 16 molecular formula C 8 H 18 octane
petrol
C H 3 (C H 2)5C H 3 condensed structural formula (C H 3 )2(C H 2)6

Alkanes are generally not very reactive but they are combustible and bur n well without much soot.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 3 of 107
 Organic Molecules - Naming and Formulae NOTES
Alkene series
A carbon chain can also contain a covalent C = C double bond joining two carbon atoms together.
The second bond joining the two "feet" is not as strong as the first bond joining the two "hands".
ethene Two H atoms must go as the double bond forms.
H H
C 2H 4
H C= C H

C H 2C H 2 H 120º
H

120º C C
The alkene functional group is a carbon-carbon double bond in a hydrocarbon. H
H
120º
Propene
The bond angles in ethene C2H4

General formula for alkenes : C n H 2n

H H H H
1 1 H H
2 3 or 3 2 C C C H H C C C
H H H H

propene C3 H6 propene
The same molecule
is just turned around. CH2 CH CH3 CH3CH CH2
Count from the left. The double bond is on C atom 1. Count from the right. The double bond is on C atom 1.
We can leave out the number as it is the same number 1 from either side.
But-1-ene or but-2-ene

1 2 4 3
1 3 4 2 1
2 3 4
a different molecule

H H H H H H H H H H H H
C C C H C C C H C C C C H
C H C H
H H H
H H H H
( infixed number ) but-2-ene
but-1-ene but-2-ene

Positional isomers have the same molecular formula but different positions of the double bond.
The same functional group appears in a different position.
Count the carbons from the left or from the right until the start of the double bond. Use the smaller number.

An alkene ( or olefin ) is an unsaturated chemical compound containing at least one C = C covalent double bond.
Unsaturated compounds are compounds with one or more multiple bonds between C atoms in their
hydrocarbon chains. (Definition)

( From the right hand side ) pent-2-ene ( From the left hand side ) hept-3-ene

H H H H H H H H H H H H
H C C C C C H H C C C C C C C H
H H H H H H H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 4 of 107
 Organic Molecules - Naming and Formulae NOTES
Alkenes are more reactive than alkanes. and being combustible they serve as a source of energy.

Ethene C2 H4 is the most important organic chemical used in industry. It makes a wide range of plastics.
Ethene is used to ripen bananas and citrus fruit. Ethene makes plastic juice bottles and milk bottles

Ethene ripens green bananas

and makes plastic squeeze
bottles for drinking water and
juice.

The bananas are picked when green so that

they do not rot when stored. Then ethene
quickly ripens them when they are needed.
Single bond
Alkanes, with strong single bonds, take long to react as this strong bond must first snap before a
reaction can happen which is caused by another atom or atoms joining onto each snapped bond.
Consider an alkane reacting with another molecule., say Br2.

H H H The single bond is a This single C ‒ H bond has to

H
pair of electrons snap before H can be replaced
H C C C C H + Br ‒ Br between two nuclei with say a Br atom.
H H H H
H H H H
‒
e C C C
sigma bond H C H
C nucleus + + H nucleus + +
e‒ H H H H
single bond 1 strong sigma bond.

H H H H
Breaking a strong C ‒ H bond requires a lot of energy.
Thus the reaction tends to happen slowly.. H C C C C Br

Double bond H H H H
C C 1 strong sigma bond
1 weak pi bond.

Alkenes, with C = C double bonds, react much faster than alkanes as they only snap the weak pi bond.
There is no need to snap the strong sigma bond.
Consider ethene reacting with another molecule, say Br2. H H H snaps H
H weak
H
C=C + Br ‒ Br C C C C
H H strong
H H H H
‒
e The weak pi bond snaps easily to create two
single bonds that can join to the Br atoms.
pi bond + + + + H H
double bond e‒ Br C C Br
H H
The sigma bonds are strong because the bonding electron-pair are trapped directly between the two carbon nuclei.
The second bond, the pi bond, is weaker as the bonding electron-pair are offset because the electron pair
forming the sigma bond repel them further away from the nuclei and thus they are more weakly held by the nuclei.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 5 of 107
 Organic Molecules - Naming and Formulae NOTES
Test for alkenes : Alkenes decolourise yellow-brown bromine water rapidly.
To make bromine water : add a few drops of JIK ( not colour fast bleach.) to some dilute HCℓ to make chlorine
water. The yellow-green colour of Cℓ2 in suspension can be seen.
Pour a little of this chlorine water into a KBr solution in a test tube.
The yellow brown ( amber ) colour of bromine water is visible as the Br2 somehow remains in suspension..
From the E-Standard Table of reduction potentials :

Br2 + 2 e‒  2 Br ‒ + 1,09 V less positive about the forward reaction. ∴ favours reverse reaction.

Cℓ2 + 2 e‒ → 2 Cℓ ‒ + 1,36 V more positive about the forward reaction.

Cℓ2 water

2 Br ‒ → Br2 + 2 e‒ Swop the reverse reaction around.

Cℓ2 + 2 e‒ → 2 Cℓ ‒
bromine Br2
Cℓ2 (aq) + 2 Br ‒ (aq) → 2 Cℓ ‒ (aq) + Br2 (aq) Jik chlorine water
water Br ‒
HCℓ
Arrows must point to the right as products form on the right. Cℓ2 K+ KBr

Add a little of this Br2 water to colourless cyclohexene.

Shake the mixture. The colour disappears quickly.
If you use cyclohexane you would have to leave the mixture over night to get rid of the Br2 water
colour as there are no double bonds to quickly snap.
Light and heat can speed up this reaction.
cyclohexene
The concentration of the HCℓ affects the colour of the bromine water which can
range from yellow-brown to red if the HCℓ is fairly concentrated.

We distinguish between saturated and unsaturated hydrocarbons using bromine water.

Instead of bromine water, one could use a purple potassium permanganate solution.
This is safer. Bromine is far more poisonous.
The purple colour of KMnO4 quickly disappears when added to cyclohexene.
KMnO4

potassium permanganate
cyclohexene
alcohol KMnO4
thermometer
Liquid bromine Br2
Liquid mercury.

poison
Never work with liquid bromine or with liquid mercury. They are deadly poisonous. Do not use a
mercury thermometer ( it may break ). Rather use an alcohol thermometer that has a red liquid in it,

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 6 of 107
 Organic Molecules - Naming and Formulae NOTES
A functional group is a reactivity centre as it forms the centre of chemical activity in the molecule.

A functional group is a bond or an atom or a group of atoms that determine(s) the physical and
chemical properties of a group of organic compounds. (Definition)
The functional group is the cause of the similar chemical behaviour of all the members of a homologous
series.
oxy-acetylene
An alkyne has a carbon-carbon triple bond C ≡ C
180º
welder
H C C H
ethyne CH CH or ( CH )2
C2 H2
or acetylene
is used for cutting and welding iron and steel. A lot of thermal energy
is released when the strong triple bond snaps.
Propyne is a gas.

H
H C C C H
H

propyne
H H H H
C3 H4
H C C C C H H C C C C H
CH C CH3 H H H H

To make the third bond, two more H atoms must go. but-1-yne C4 H6 but-2-yne
• alkynes are unsaturated with a general formula Cn H2n – 2
• alkynes are combustible and serve as a source of energy eg. oxy-acetylene blowtorches used for welding and
cutting of metals burn ethyne ( acetylene ) in a stream of O2 gas.

Homologous series are 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.

H H H H H H H
H C C C C C H H C C C C C C H

H H Keep adding a CH2 to make the

H H H H H
chain longer.
pent-2-yne C5 H8 hex-2-yne C6 H10
The triple bond is the
functional group. Number from the end closest to the triple bond.
Unsaturated compounds do not have the maximum number of hydrogen atoms attached to the carbon atoms.
Bond types first pi bond e‒ two pi bonds
sigma bond
C nucleus + + C nucleus + + C nucleus
+ +
single bond
double bond triple bond

C C Alkynes react fastest if they only have to snap the one very weak pi bond.
H H H H H H e‒
The inner pi electrons
1 strong sigma bond C C C C C C shield the outer pi electrons
1 weak pi bond snap from the nucleus, making it
1 very weak pi bond H H H H H H easier to remove them.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 7 of 107
 Organic Molecules - Naming and Formulae NOTES
Halo-alkanes ( or Alkyl halides ) have halogen atoms bonded to a C atom in a saturated hydrocarbon.
• substitute one or more H-atoms with halogen atoms naming the halogens in alphabetical order
• a halogen which replaces a H-atom is called a substituent
• ignore prefixes di-, tri- etc when working out alphabetical order
• write the whole name as one word putting the halogens first
• number from left and then also from right before choosing the smaller number
• number the longest chain beginning at the end nearest the first substituent, be it an alkyl group or a halogen
Use the smaller numbers.
F ozone destroyer
F Br Cℓ H H

H C H Cℓ C C C Cℓ F C Cℓ
C
H H H H H H
chlorodifluoromethane
1-bromo-2-fluoroethane 1,1,3-trichloropropane
Chlorofluorocarbons. CFC
( alphabetical preference ) not
Aerator in aerosol cans,fridges and
1,3,3-trichloropropane
car air conditioners.
F Cℓ
Br F
1
1 Cℓ F Cℓ
Cℓ

H Br
mono ( 1 )
di ( 2 ) Cℓ Br Cℓ
H C C H
tri ( 3 ) Cℓ C C C
I I H
tetra ( 4 )
1-bromo-1,2-diodoethane H H Br
The right hand C has more substituents, dichloromethane 1,2-dibromo-1-chloroethene
so it becomes carbon number one. less toxic laboratory solvent
Br
Cℓ
Br Primary halo-alkane.
Halogen attached to end 1
1 carbon atom that is only Cℓ
Cℓ
attached to one other C
atom.
I
Br
I Ignore the prefixes di- and tri- in the names.

• adding more halogen atoms make halo-alkanes more poisonous, less combustible and less water-soluble
• used in fire extinguishers but the poisons they emit are causing a return to CO2 fire extinguishers
• used as refrigerants and as a domestic cleaning agent ( oven window cleaners, toilet bowl cleaners )
• halo-alkanes are used as solvents and anaesthetics ( CHCℓ3 trichloromethane or chloroform )
Cℓ
CHCℓ3
• CCℓ4 is non-polar, does not dissolve in water and does not bur n but is very toxic.
CCℓ4 was banned as an ozone destroyer by the Montreal Protocol of 1986. Cℓ
All CFCs were also banned.
Cℓ
H Cℓ H H H H H Cℓ H H H
H C C C C C H H C C C C C C H
H H H CH3 H H H H H CH3 H
2-chloro-4-methylpentane. 4-chloro-2-methylpentane.
4-chloro-2-methylpentane. 3-chloro-5-methylpentane.
Both chloro and methyl can be 2. Write out both methyl gets preference as it is closer to the end.
names and choose the lower number where they
first disagree
F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 8 of 107
 Organic Molecules - Naming and Formulae NOTES
Substituents ( Side chains and atoms )
A substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a
hydrocarbon.
A substituent is a piece that is attached to a carbon chain, that must be longer than the substituent, and gives
rise to a branched chain if the substituent has one or more carbon atoms ( an alkyl group ).

• the longest possible chain of C atoms gives the name of the compound C5 H11 Cℓ
• straight chains and branched chains are called aliphatics
C4 H9 Cℓ Cℓ

Cℓ Cℓ

2-chloro-2-methylbutane
1-chlorobutane 2-chlorobutane ( halogens before side chain )
Cℓ is a substituent. Cℓ is a substituent. CH3 CCℓ (CH3) CH2 CH3
CH3 CH2 CH2 CH2Cℓ CH3 CHCℓ CH2 CH3 Cℓ and methyl are substituents.
primary haloalkane secondary haloalkane tertiary haloalkane
Cℓ bonds to a C atom that is Cℓ bonds to a C atom that is Cℓ bonds to a C atom that is
joined to one other C atom. joined to two other C atoms. joined to three other C atoms.

Butane is the main chain. Cℓ is a substituent.

The methyl group is a substituent and a side chain ( an alkyl group ). The side chain appears in brackets.

This long chain is octane C8 H18

H H H H H H H H
H C C C C C C C C H
H H H H H H H H octane C8 H18
H H
methane
H C H methyl H C H side chain is an alkyl group
CH4 CH3–
H

Attach two methyl substituents.

H H
H C H H C H
H H H H H H
H C C C C C C C C H
H H H H H H H H
CH3 CH(CH3) CH2 CH2 CH2 CH(CH3) CH2 CH3 2,6-dimethyloctane C10 H22
Attach an ethyl substituent

C 2H 5– H
H C H
H H
H C H
H C H H C H
H H H H H
H C C C C C C C C H
H H H H H H H H 4-ethyl-2,6-dimethyloctane C12 H26
CH3 CH(CH3) CH2 CH(C2H5) CH2 CH(CH3) CH2 CH3 ethyl comes before methyl alphabetically.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 9 of 107
 Organic Molecules - Naming and Formulae NOTES

Structural isomers are organic molecules with the same molecular formula but different structural formulae.
( Definition )
There are 3 types of structural isomers : positional isomers, chain isomers and functional isomers.

Positional isomers have the same molecular formula but different positions of the side chain, substituents
or functional groups on the parent chain. ( Definition )
Write down the name for
CH3 CH2 CH(CH3) CH2 CH2 CHBr CH3
CH3 CH(CH3) CH2 CHBr CH2 CH3 and

CH3 Br
CH3 Br
I I
I I CH3 CH2 CH CH2 CH2 CH CH3
CH3 CH CH2 CH CH2 CH3
4-bromo-2-methylhexane 2-bromo-5-methylheptane
( methyl is closest to an end ) ( bromo is closest to an end )

Br Br

Alcohols
Alcohols ( alkanols ) have the ̶ OH hydroxy group bonded to a saturated C atom.
Alcohols are organic compounds containing the hydroxy group.
The hydroxy group ‒OH is the functional group.
methane CH4 methanol CH3OH ethanol ( wine ) C2H5OH
H Methane H H H
becomes H H
H C H methanol. H C O H C C O
H H H H
Notice that the alcohols are named by dropping the final “e” of the alkane name and adding “ol”:

CnH2n + 1 OH O
O
Alcohol general formula molecular model
OR CnH2n + 2 O

H O ball-and-stick model
H H O H butan-2-ol
H C C C C H
H H H H
butan-2-ol
1
The 2 is an infixed number. ( or locator number )
The OH is attached to the second C-atom.
Counting from the left, the OH is attached to the third C atom,
but from the right, the OH is attached to the second C atom.
Rule : always count from the side that is closest to the functional group. So the right hand C-atom is number 1.

Alcohols are formed when one hydrogen from an alkane is substituted for, by a hydroxy or ‒ OH group.
Alcohols are combustible and serve as a source of energy. They are very useful as solvents.

Homologous series are 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.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 10 of 107
 Organic Molecules - Naming and Formulae NOTES
Primary Alcohols ( C atom at the end of a chain )
A primary alcohol is one in which the carbon having the
H H H
- OH ( hydroxy ) group is bonded to only one other carbon H
atom. H C C C O O
H H H
propan-1-ol ( C3H7OH )
Number from the end closest to the OH group.
Secondary Alcohols ( C atom inside a chain )
In a secondary alcohol the carbon to which the hydroxy H
O
group is attached is also bound to two other carbon H O H
atoms.
H C C C H
propan-2-ol ( C3H7OH ) H H H

Tertiary Alcohols need a side chain H

In a tertiary alcohol, the carbon which holds the H O H O
hydroxy group is bonded to three other carbon
groups. H C C C H
H H
methylpropan-2-ol ( C4H9OH ) H C H
H
Identical molecules
H H
H H
H C H H O
H C O O C H
O H C H
H H H
H
H
Rotate the methanol molecule anti-clockwise. This does not change the molecule.
methanol
CH3OH or CH4O This formula describes all four molecules.

O O
O

H H H
H R – OH
H C C C O propan-1-ol can represent any alcohol.
R represents any C chain or alkyl group.
H H H

alkyl group parent group sugar cane

functional
R group

Ethanol can be produced by fermentation of plant material

e.g. maize and sugar cane.

maize / mealie

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 11 of 107
 Organic Molecules - Naming and Formulae NOTES
Carboxylic Acids
O
Carboxylic acids end in – COOH ( called an "– oic acid" ) II
The functional group for carboxylic acids is – COOH ( carboxyl group ) ‒C‒O‒H

This O draws the electron density

from the C, further polarising the
O–H bond and making the H more
positive.

O H O vinegar H H H O
H H H
H C O H C C O H C C C C O The molecule donates
H H H H this H+ when acting
as an acid.
methanoic acid ethanoic acid butanoic acid
HCOOH C H3 COOH C3 H7 COOH
O pulls harder on
Old name is acetic acid.
the bonding pair of
Vinegar is a 5% solution of acetic acid O •• H electrons and pulls
them away from the
H atom to make H
slightly positive.
O O O
O O O

Butanoic acid, when ionizing in water, forms

O
O • •+
H+ hydrogen ion
butanoate ion C3 H7 COO‒
Dissolve vinegar in water.
It behaves as a typical monoprotic acid ( one acid molecule donates one H+ ion ) to produce hydronium ions.

C H3COOH (aq) + H2O (ℓ ) → CH3COO‒ (aq) + H3O+ (aq)

O O
• +
O
O O •
O
hydronium ion

medicine dropper

add bromothymol blue

indicator

drop
Add a few drops of the indicator bromothymol blue
to some colourless vinegar ( ethanoic acid ).
The colour of the vinegar changes to yellow.
This proves that vinegar is an acid,
colourless yellow
vinegar

vinegar

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 12 of 107
 Organic Molecules - Naming and Formulae NOTES
Esters
Esters are slightly oily and have a pleasant aroma associated with fruit and vegetables.
They are formed by combining alcohols and carboxylic acids.
Write down the two formulae with the functional groups facing each other. Put the alcohol on the left hand side.
For example, combine propanol and ethanoic acid.
H H H O H
I I I II I Write the acid formula backwards so that the two
H‒C‒C‒C‒O‒H + H‒O‒C‒C‒H functional groups face each other.
I I I I
H H H H
Draw an oval around the elements that make
H H H O H water. The acid, with two oxygen atoms, provides
I I I II I the oxygen.
H‒C‒C‒C‒O‒H + H‒O‒C‒C‒H
Add a few drops of the dehydrating agent
I I I I
concentrated sulfuric acid to remove this water.
H H H H
H H H O H O
I I I II I II I
H‒C‒C‒C‒O‒C‒C‒H ‒C‒O‒C‒ ester functional group
I I I I I
H H H H
propyl ethanoate The ester name is two words.
Many esters have a pleasant fruity aroma and are used in the fragrance and flavour industry.
Examples of ester aromas are
apple pineapple pear orange banana

O O
Ketones II I II I
Ketones have the carbonyl group ‒ C ‒ bonded to two C atoms. ‒ C ‒ C ‒ C ‒
• ketones usually have aromas that resemble food I I
• ketones produce the fragrance of camphor
• the ketone functional group is : O ( R and R ’ represent any alkyl chain eg. methyl, ethyl )
H O H || Ketones have 2 alkyl groups ( R and R' ).
C The carbonyl group is never on an end C for ketones.
H C C C H R R’
H H H O H H H pentan-2-one
propanone
pronounced “ propa known ” H C C C C C H
O ( simplest ketone )
H H H H
Called acetone. O
II
Condensed structural formula
does not show all the bonds CH3CCH2CH2CH3

• the ketone functional group is on the second carbon ( or any other inner carbon atom )
• the ketone double bond is never on an end carbon
• number the longest chain beginning at the end nearest the carbonyl group ( or keto group )
Ketones are used Acetone is a ... Acetone is
as solvents. solvent Ketones are used a nail polish
and an antiseptic as paint thinners, remover
cleaning agent in
laboratories.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 13 of 107
 Organic Molecules - Naming and Formulae NOTES
Aldehydes have the formyl group O O
which is the carbonyl group and a H atom. || The C is always an end C. ||
( also called the aldo group ) –C–H R –C–H
To form an aldehyde, shift the double bond holding the O atom ( the carbonyl group ) to an END atom.
Thus an aldehyde only has one alkyl group ( R ).

O H O H H O aldo group
C C H O
H C H H H C C C H
II
H H H CH3 CH2 CH
H CHO CH3 CHO CH3 CH2 CHO
methanal ethanal Condensed structural formula
propanal
does not show all bond lines
O O O
aldo group

1
• number the longest chain beginning at the end nearest the aldo group which is always carbon number 1

• aldehydes can have aromas that resemble food such as vanilla and spearmint.

mint coating of
vanilla flavouring chewing gum

General formula for both ketones and aldehydes: Cn H2n O

H H H H H O H H O H H H
H C C C C C C H H C C C C C C H
H H H H H H H H H H hexan-3-one
hexanal C6H12O
CH3(CH2)4CHO CH3CH2 CO (CH2)2CH3

O O

Functional isomers have the same molecular formula, but different functional groups. (Definition)

The ketone and aldehyde can also be regarded as functional isomers as they involve different functional groups.
H H H O H general formula for both : Cn H2n O2 H H H H O
H
H C C C O C C H molecular formula for both : H C C C C C O
H H H H C5 H10 O2 H H H H

propyl ethanoate pentanoic acid

Esters and carboxylic acids form
functional isomers O
O

O O

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 14 of 107
 Organic Molecules - Naming and Formulae NOTES

Positional isomers have the same molecular formula but different positions of the side
chain, substituents or functional groups on the parent chain. (Definition)

The same functional group appears in a different position.

Use numbers to differentiate the C atoms H H H H
H H H H
Count the C atoms from the side closest to the C C C C H H C C C C H
double bond H H H H H
Separate letters and numbers with a hyphen. but-1-ene C4 H8 but-2-ene C4 H8

C4H10O
1 1
H
O H
H O H H O H H H O
H C C C C H H C C C C H
H H H H H H H H
butan-2-ol
butan-1-ol

Br
C 4H 9F Br
H Br H H Br H H H
H C C C C H H C C C C H
H H H H H H H H
2-bromobutane 1-bromobutane

C6H12O

hexan-2-one hexan-3-one
O
O

CH3CHO (CH2)3CH3 CH3(CH2)2CHO CH2CH3

C7H16

2-methylhexane 3-methylhexane

CH3CH(CH3) (CH2)3CH3 CH3(CH2)2CH(CH3) CH2CH3

H H
I I
H‒C‒H H‒C‒H

H H H H H H H H
H H
H C C C C H H C C C C C C H
C C
H H H H H H H H H H H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 15 of 107
 Organic Molecules - Naming and Formulae NOTES

Chain isomers have the same molecular formula but different types of chains. (Definition)

The atoms are arranged in different chains. H H H H H upside down T

A side chain makes a T- junction. C H C H
H C C C H T
H H H H
H H H
H H H
H C H H C C C H
H C C C C C H
H H H T
H H H H methylbutane
H H C H

pentane H H H H H
H C C C C H dimethylpropane
H H H
H C H T

methylbutane

The following are not chain isomers of hexane.

The longest chain ( parent chain ) does not have to be a straight line.
The longest chain forms L - junctions if it is not a straight line. H
These 5 formulae are just different ways of writing “hexane”.
H C H
H H H H H H
L H H H H
H C C C C C C H
H C C C C C H
H H H H H H
Hexane H H H H H
Hexane
H

H C H

H C H
H H H
L
H C H H C C C H H
L H H H H H
H C H H C H
H C C C C H
Hexane
H H H
L H C H
H
H C H L H H H
H C C C C H
Hexane upside down L
H
flipped horizontally H H H H
Hexane
Hexane

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 16 of 107
 Organic Molecules - Naming and Formulae NOTES
Esterification Making an Ester
Esters cause identifiable aromas ( like the fragrant smell and odour of fruit ) and are used in perfumes.
CAUTION
However, the smells of fruits are due to the presence of complicated mixtures of chemicals, some of
which are not always esters, rather than solely one ester. But individual esters are often important components in
an aroma.
Different people sometimes get a different aroma from the same ester.
Though the size of the molecules varies, it seems that the presence of the COO group is vital to the kind of smell.
Butanoic acid is present in rancid butter and human vomit. So there are people who prefer not to use it to make an
ester as it can be a bit tricky to get its esters to smell nice.
Different people may use different quantities of sulfuric acid relative to the quantities of alcohol and carboxylic acid.
Many people use equal quantities of carboxylic acid and alcohol but some prefer a small excess of alcohol
( say 5 mℓ ) compared to the carboxylic acid ( say 4 mℓ ).
Three different methods are described. See which works best for you. Or try your own variation.
Method concentrated H2SO4
concentrated H2SO4
ethanol ethanoic acid Mixture of
medicine dropper ethanol and
ethanoic acid 5 drops
10 drops

OR

2 mℓ 2 mℓ 4 mℓ

test tube 1 cm 1 cm
measuring cylinders Mixture of C2H5OH CH COOH
3
ethanol and
ethanoic acid 1 cm acid and 1 cm alcohol. 5 drops H2SO4.
1) Using small measuring cylinders, place 2 ml of ethanol and 2 ml of ethanoic acid in a clean dry test tube.
2) While stirring the contents of the test tube with a glass rod add 10 drops of concentrated sulfuric acid very
slowly, allowing the drops to slide down the sides of the test tube, using the propette or medicine dropper.
Sulfuric acid is very exothermic when in contact with an aqueous solution of ethanoic acid so there must be time
for the thermal energy to disperse. Otherwise the hot, corrosive solution can shoot out of the test tube.
OR
Measure 5 mℓ of alcohol and add to it 5 mℓ of carboxylic acid. Carefully add 4 drops of concentrated H2SO4.
OR another method which is probably simpler.
Measure the alcohol and carboxylic acid by their height in a test tube rather than using measuring cylinders.
Soak filter paper in cold water. Hold it over the test thermometer
Boil water in a kettle. tube mouth using a rubber band. This stops the ester
Pour some into a beaker. filter paper
fumes escaping. The cold makes the ester gas
condense and flow back into the test tube ( reflux ).
OR
filter paper Ethyl ethanoate boils at 77ºC.
It is very volatile. Heat the
beaker water to just below the ester’s
boiling point.

porcelain chips
75 ºC
boiled
water from hot water bath
60 ºC ‒ 75 ºC
kettle
Hot plate

3) Heat the test tube in a beaker of hot water for about 6 minutes. The water must be at a temperature of about
75 oC. Add more hot water to the beaker if necessary to keep the temperature up.
OR Place the test tube in water that is in a beaker and heat the water on a hot plate to a temperature of about
60˚C – 75˚C. Leave the test tube in the hot water bath for 15 minutes.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 17 of 107
 Organic Molecules - Naming and Formulae NOTES
If the mixture in the test tube boils, lift the test tube out of the hot water so that it can cool a little then replace the
test tube in the hot water again.
Putting one or two small porcelain chips into the mixture in the test tube can help to stop it bubbling, to some
extent.
Do not use a flame to heat the water. The alcohol vapour is very flammable and can catch alight.
4) Remove the test tube from the hot water and place it in a beaker of cold water for about two minutes to allow it
to cool. But the ester aroma is often masked or distorted by the smell of the carboxylic acid.

water

15 ºC insoluble less dense ester floats on the surface

cold water bath cold mixture ethanol, ethanoic acid and sulfuric acid all
dissolve in the added water.

5) Remove the filter paper and add 5 ml of distilled water to the test tube.
The reason for adding water to the contents of the test tube is to separate the ester from the alcohol, the
carboxylic acid and the sulphuric acid. Esters are soluble in alcohol, but except for the very small esters they are
insoluble in water, and they generally have a density less than that of water, enabling them to separate and float
to the top of the liquid mixture and tend to form a thin layer on the surface. Excess acid and alcohol both dissolve
and are tucked safely away under the ester layer.
This makes the detection of the odour more reliable.
But the smell of the acids can mask the ester aroma. It may help to neutralise the acids with a base.
Make a solution of about 20 mℓ of sodium hydrogencarbonate in water.
Not all the reaction mixtures will form two
layers.
Some mixtures will be colourless,
others will be yellow or even dark brown.
NaHCO3 solution in water insoluble ester forms a thin layer on top

Slowly pour the contents of the test tube into the basic solution that is in the beaker.
Effervescence occurs as the base neutralises the acids. The mixture can be stirred.
Then waft the ester vapours towards your nose, holding the beaker about 30 cm in front of you and about 15 cm
below your nose.
But first, move away and take a big breath of uncontaminated air as you do not want to breathe in these fumes.

Gently waft the ester

vapour fumes towards
your nose. These fumes
carry the aroma.

ester fumes Sniff cautiously.

Do not breathe deeply.

Because esterification reactions are slow at room temperature and reversible, you don’t get a lot of ester produced
in a few minutes.

In order to speed the reaction up and get an appreciable yield in the time available, use a temperature of about
60°C - 75°C and add sulfuric acid to act as a catalyst in the reaction.
The catalyst mechanism goes through a number of steps and this is a fairly complex mechanism.
Salicylic acid is a non-polar solid that does not dissolve in water. Dissolve it in the ethanol.
Use 1 gram of acid powder ( a small scoop ) for every 3 mℓ of alcohol and then add a few drops of
concentrated H2SO4. The ester yield is low but the aroma is distinct. Try using a Disprin or Asprin

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 18 of 107
 Organic Molecules - Naming and Formulae NOTES
Esterification is an acid catalysed condensation between an alcohol and a carboxylic acid.

The double bond is on the acid side of the molecule.

alcohol donates H acid donates OH ( to form water )
H H O H H2SO4 H H O H H H
H H O
H C C O + O C C H → H C C O C C H +

H H H H H H ester

ethanol + ethanoic acid → ethyl ethanoate + water

Boiling point 77 ºC
O

O O
O
O

H2SO4 extracts H and OH. This is an elimination reaction. Condensation as H‒OH forms
Concentrated H2SO4 is a strong dehydrating agent.
O water

The equilibrium constant is not too far from being 1, thus the reaction does not really proceed by itself.
We need to drive the equilibrium to favour the forward reaction (using Le Chatelier’s Principle) in order to make
the ester.
This is done by removing the water chemically using excess sulfuric acid as a dehydrating agent.
The forward reaction is then favoured to replace the missing water.

This is a condensation reaction, in which two molecules link up by the elimination of a small molecule
between them; in this case, water.
warning sign
When the alcohol was made from radioactive oxygen-18 then no traces of
radioactivity were found in the water that formed as a product. Thus the oxygen
in the water does not come from the alcohol. It must thus come from the acid.
The concentrated sulfuric acid extracts an H and an OH to form water.

AROMAS :
methyl ethanoate Glue or nail polish remover. Methyl ethanoate is a solvent for glue.
methyl salicylate Wintergreen (smell of iodine)
ethyl ethanoate fruity, glue or nail polish remover
3-methylbutyl ethanoate Banana smell
pentyl salicylate Floral smell
pentyl ethanoate Pear smell O
O
Functional group for esters : II
– C – O – C ‒ ester group alcohol R – O – C – R ’ acid

hexyl propanoate H H H H H H H H R and R’ represent alkyl groups

H C C C C C C O C C C H Eg. methyl. ethyl, propyl, butyl,
pentyl, hexyl, heptyl, octyl
H H H H H H O H H

Esters has many uses, such as artificial fruit essences and aroma enhancers, artificial flavours for confectionery,
ice cream and cakes, as a solvent in many applications (including decaffeinating tea and coffee) for varnishes and
paints (nail varnish remover), and for the manufacture of printing inks and perfumes.

cakes ice cream printer’s ink solvent perfume paint solvents

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Page 19 of 107
 Organic Chemistry Activities 1 Naming and Formulae
1. ( Memo Page 31 - 32 )
Define what is meant by
1.1 Organic molecules 1.2 Hydrocarbons
2.
For the molecule butane write down
2.1 the structural formula. 2.2 the condensed structural formula. 2.3 the molecular formula.
3.
3.1 What does n-alkane mean ? 3.2 Write down a structural formula for propane.
3.3 Write down a condensed structural formula for hexane. 3.4 Write down a molecular formula for octane.
4.
Define what is meant by
4.1 a structural formula 4.2 a condensed structural formula
4.3 a molecular formula 4.4 saturated compounds
4.5 unsaturated compounds
5.
5.1 Write down the general formula for alkanes. 5.2 How many C-atoms in heptane?
5.3 Alkanes are generally ( active / unreactive ). 5.4 Alkanes bur n ( well / poorly ).
5.5 When alkanes burn they produce ( much / little ) soot. 5.6 Alkanes ( are / are not ) a major fuel source.
6.
Write down the
6.1 structural formula for 6.1.1 hexane 6.1.2 propane 6.1.3 methane
6.2 condensed structural formula for 6.2.1 hexane 6.2.2 propane 6.2.3 methane
6.3 molecular formula for 6.3.1 hexane 6.3.2 propane 6.3.3 methane
7.
Write down the
7.1 structural formula for 7.1.1 hex-2-ene 7.1 2 propene 7.1.3 hex-3-ene 7.1.4 pent-1-ene
7.2 condensed structural formula for 7.2.1 hex-2-ene 7.2 2 propene 7.2.3 hex-3-ene 7.2.4 pent-1-ene
7.3 molecular formula for 7.3.1 hex-2-ene 7.3 2 propene 7.3.3 hex-3-ene 7.3.4 pent-1-ene
8.
How can we prove that an alkene reacts faster than an alkane?
9.
Write down the
9.1 structural formula for 9.1.1 hex-2-yne 9.1.2 propyne 9.1.3 hex-3-yne 9.1.4 pent-1-yne
9.2 condensed structural formula for 9.2.1 hex-2-yne 9.2.2 propyne 9.2.3 hex-3-yne 9.2.4 pent-1-yne
9.3 molecular formula for 9.3.1 hex-2-yne 9.3.2 propyne 9.3.3 hex-3-yne 9.3.4 pent-1-yne
10.
Define what is meant by
10.1 a functional group 10.2 a homologous series
11.
Write down the general formula for 11.1 an alkene 11.2 an alkyne
12.
Write names for the following
12.1 12.2 12.3 12.4 12.5
Cℓ F H H Cℓ
F H
Cℓ C H H H Br C C C Br
H C C H F C H C
C
Cℓ Br H H H
Cℓ Cℓ Cℓ Cℓ
Br H H
12.6
12.7 12.8 12.9 H C C C C C H
Br Br H H
Br H
H H H
H C C C H I C C H H C C C H

H Cℓ H Br H
H
13.
Write structural formulae for
13.1 2-chlorohexane 13.2 3-chloro-2-iodopentane 13.3 5-chloro-1,2-difluorohex-3-ene

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 Page 20 of 107
 Organic Molecules - Naming and Formulae ACTIVITIES 1
14. ( Memo Page 32 - 33 )
Write structural formulae for
14.1 CH3 CH(CH3) CHBr CH2 CH3 14.2 CH3 CH(CH3) CH2 CH2 CH2 CH(CH3) CH2 CH3

14.3 CH3 CH = CHCH2 CH(CH3) CH3

15.
Write down the names for the following
15.1 H 15.2 15.3 H
H Br Br H H H
I I I I I I I
H ‒ C ‒H H C H
H‒C‒C‒C‒C‒C‒C‒H
H H I I I I I H H
I I H H H H H
H‒C‒C ≡ C‒C‒C‒H H C C C C Br
H‒C‒H
I I I I H
H H H Br
H‒C‒H
H C H
I
H H
16.
Define a 16 .1 structural isomer 16.2 positional isomer

17.
Write down a name for CH3 Br
17.1 CH3 CH(CH3) CH(C2H5) CHBr CH2 CH3 17.2
I I
CH3 CH2 CH2 C CH2 CH2 CH CH3
I
18. CH3
18.1 Define a homologous series.
18.2 Write down a name for
18.2.1 18.2.2 H 18.2.3 H
H H H H H O O H H
H H H H H H
H C C C C O H
H C C C C H H C C C C C C
H H H H
H H H H H H H H H H

18.3 Which formula represents a

18.3.1 tertiary alcohol 18.3.2 primary alcohol 18.3.3 secondary alcohol
A B C
H H H H H
H O H H O H H
H C C C O
H C C C H C C C
H H H H H
H H H H H
H C H
19. H
Write down a structural formula for
19.1 methanol 19.2 butan-1-ol . 19.3 heptan-3-ol
20.
Write down a structural formula for
20.1 methanoic acid 20.2 ethanoic acid 20.3 butanoic acid

21.
Write down a name for
21.1 H 21.2
H O H H H H O
H H
H C C C O H C C C C C O
H H H H H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 Page 21 of 107
 Organic Molecules - Naming and Formulae ACTIVITIES 1
22. ( Memo Page 33 - 34 )
Write down a name for
22.1 22.2 22.3
O
H H H H O H H H O H H II
I I I I II I I
H‒C‒C‒C‒C‒O ‒C‒C‒C‒H H C O C C C H CH3 CH2 ‒ O ‒ C CH2 CH3
I I I I I I H H H
H H H H H H
23.
23.1 Write down the structural formula for ethyl methanoate
23.2 Write down the structural formula and name and type of isomer of an isomer of ethyl methanoate.
23.3 Write down the structural formulae and names of two isomers of pentan-2-one.

24.
Define a 24.1 functional isomer 24.2 positional isomer
25.
Write names for :
25.1 25.3
25.2
H O H H H H O H H O H
H C C C C H H C C C C H H C C C H
H H H H H H H H

25.4 25.5
H H O H H H H H H O H H H H
H C C C C C C C C H H C C C C C C H
H H H H H H H H H H H H
25.6 25.7 25.8
O H H O H H H
H H H H O H
H C C C H H C C C C C H H C C C C C H
H H H H H H H H H H

25.9 25.10 25.11

O H H H
H O O H H H H H
H C C C C H
H C C H H C C C C C C H
H H H
H H H H H H
26.
Write down structural formulae and names for
26.2 26.3
26.1
CH3 CH2 CO CH2 CH3 CH3(CH2)3CO(CH2)2CH3 CH3(CH2)2CO CH2CH3

26.4 26.5 CH (CH ) CHO

3 2 4
CH3(CH2)2CHO

27.
Define
27.1 functional isomers 27.2 positional isomers 27.3 chain isomers

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 Page 22 of 107
 Organic Molecules - Naming and Formulae ACTIVITIES 1
28. ( Memo Page 34 - 36 )
Write down the names and structural formulae and molecular formulae for two positional isomers of
28.1 hex-1-ene. 28.2 pentan-2-ol 28.3 1,2-dibromopropane

H H H H H H C5H12O Br Br H
H
C C C C C C H H C C C H
H O H H H
H H H H H H H H
H C C C C C H
C6 H12
H H H H H

28.4 hex-1-yne C6 H10 28.5 1-bromo-2-chloropropane 28.6 heptan-3-one

H H H H Br Cℓ H O H H
H H H H
H C C C C C C H H C C C H C C C H
H C C C C
H H H H H H H H H
H H H H

29.
Write down the structural formula and semi structural formula of two positional isomers of 2-methyl heptane.

CH3CH(CH3) (CH2)4CH3

30.
Write down the names and structural formulae and molecular formulae for a functional isomer of
30.1 propyl methanoate 30.2 pentan-3-one

H H H O
H H O H H
H C C C O C H
H C C C C C H
H H H
H H H H
31.
Which three homologous series have no positional isomers?

32.
Write down the names and structural formulae and molecular formulae for four chain isomers of hexane
33.
Name the following
33.1 33.2 ( halo-alkane ) ( alkyl halide )
H
H
H C H
H C H
H H C H
H H H
Br H H H H H H
H C C C C C H
Cℓ C C C C C C C C H
H H H H
H C H Cℓ H H H H H

H C H H C H
H C H
H H
H

34.
Write down a structural formula for

34.1 dimethylpropane
34.2 2-chloromethylpropane
34.3 2,7-dibromo-2-chloro-4-ethyl-5-methyloctane

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 Page 23 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
( Memo Page 37 )
1.1 Name the homologous series for hydrocarbons containing triple bonds.
1.2 Write down the formula of the functional group of the
1.2.1 ketones
1.2.2 aldehydes
1.3
O
II
When the functional group ‒ C ‒ is present in a compound, the compound may be …

A propanal. B propan-1-ol. C propanone. D methyl ethanoate.

1.4 Which ONE of the following compounds is saturated?

A C4H10 B C5H10 C C5H9OH D C6H10

2. Jana wants to investigate how molecular mass influences the boiling points of the first eight straight chain
alcohols.
2.1 Which property of the alcohols could make this investigation dangerous? (1)

2.2 Structural isomers can influence the outcome of this investigation. Alcohols with more than two carbon
atoms have more than one structural isomer.

2.2.1 Write down the structural formulae and IUPAC names of the structural isomers of the alcohol
containing three carbon atoms. (6)

2.2.2 Jana uses heptan-1-ol as one of the compounds in the investigation. Which ONE of the isomers
named in QUESTION 2.2.1 must she use for this to be a fair test? (1)

2.2.3 Explain the need for this choice in QUESTION 2.2.2. (2)

2.3 Design an investigation that Jana can conduct. Use the following headings in your design:

2.3.1 Hypothesis (2)

2.3.2 Precautions (1)

2.3.3 Apparatus (4)

2.3.4 Method (3)

3.1 Which one of the following represents an ester?

A C2H4O2 B C4H6O2 C C3H8O2 D CH2O2

3.2 Name a hydrocarbon of which the molecules contain a ring of six carbon atoms, with two hydrogen atoms
attached to each carbon atom.
3.3 Write down a structural formula for the carbonyl group.
3.4 Which of the following are structural isomers of hexane?

(i) CH3 ‒ CH2 ‒ CH ‒ CH2 ‒ CH3 ( ii ) CH3 ―CH2 CH3

CH2 CH3 CH2 ―CH2 ― CH2

( iii ) CH3 ‒ CH ‒ CH2 ‒ CH3

CH2 ―CH3

A (i) and (ii) only B (ii) and (iii) only C (i), (ii) and (iii) D (i) and (iii) only

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 24 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
4.1 CH3 ― C― CH2 ―CH2 ― CH3 ( Memo Page 37 - 38 )
II
O
Write down the structure of the functional group and the IUPAC name for this compound.

4.2 Esters are a group of organic compounds widely known for their pleasant odours.
The fruity smell of apple is, for example, due to the presence of ethyl butanoate.

Write down the condensed structural formula of ethyl butanoate.

4.3 What do we call compounds with the same molecular formula but different structural formulae?
4.4 The simplest ketone has three carbon atoms. Is this statement true or false? Draw and name this ketone.

4.5 The structural formulae for four compounds are shown below.
O O H O H H O
II II I II I I II
H ‒ C ‒ O ‒ H H‒C‒H H‒C‒C‒C‒H H‒C‒O‒C‒H
I I I I
H H H H
These compounds can be classified in the correct sequence as …

A Carboxylic acid, ester, aldehyde, ketone B Carboxylic acid, aldehyde, ketone, ester
C Aldehyde, ketone, carboxylic acid, ester D Carboxylic acid, aldehyde, ester, ketone

5.
Alcohols are used in a variety of chemical reactions and as preservatives in certain medicines. All alcohols are toxic.
Although ethanol is the least toxic of all alcohols, it is still a poisonous substance. It is rapidly absorbed into the
blood.
High blood alcohol levels can cause brain poisoning. The body can reduce high blood alcohol levels by oxidising
the alcohol. Contrary to what people believe, alcohol is a depressant and not a stimulant.

The following table indicates the effects of various blood alcohol levels:

The effects of blood alcohol levels

% per volume Effect
0,005 – 0,15 Loss of coordination
0,15 – 0,20 Severe intoxication
0,20 – 0,40 Loss of consciousness
0,50 Death

The liver enzyme, ADH, catalyses the oxidation of ethanol to ethanal and then to non-toxic ethanoic acid.
The liver is able to remove only 28 grams of pure alcohol per hour.

5.1 Write down the NAMES of the homologous series to which the compounds ethanal and ethanoic acid
respectively belong. (2)

5.2 Write down the structural formula of ethanal. (2)

5.3 The warning on the labels of certain medicines reads as follows:

The effect of this medicine is aggravated by the simultaneous intake of alcohol.
Use the information in the passage above to justify this warning. (4)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 25 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
6. B. ( Memo Page 38 )
Consider the organic compounds labeled A – D. H
I
A. CH3 CH2CH2CH2CH2CH3 H‒C‒H

H H O H
C. C6H12
I I II I
H‒C‒C‒C‒C‒C‒H
D. CH3 ‒ Cℓ I I I
H H H

H‒C‒H
I
H‒C‒H
I
H
6.1 Write down the IUPAC name for compound B? (2)

6.2 Use a condensed structural formula to rewrite compound A so that the longest chain has FOUR carbon
atoms. (2)

6.3 Which of the compounds are saturated? (1)

7.
7.1 What do we call the atoms, groups of atoms or bonds that can be used to identify a homologous series?
7.2 Which chemical compound is an aromatic hydrocarbon?

A. hexane B hexene C hexyne D cyclohexene

7.3 Esters and carboxylic acids can both be represented by the general formula CnH2nO2.
Is this statement true or false?
7.4 The condensed structural formula of an organic compound is given below.
CH3
I
Cℓ ‒ CH2 ‒ CH ‒ CH ‒ CH3
I
CH2
I
CH3

Which ONE of the following is the correct IUPAC name of this compound?

A 1-chloro-2,3-dimethylbutane
B 1-chloro-2,3-dimethylpentane
C 1-chloro-3-ethyl-2-methylbutane
D 1-chloro-2-ethyl-3-methylpentane

7.5
Atoms, groups of atoms or bonds that give a homologous series its characteristic properties.
7.6
Write down the name and formula of the compound that is always present in alcoholic drinks.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 26 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
8. ( Memo Page 38 - 39 )
You have two test tubes containing equal amounts of compounds X and Y respectively.
They have similar molecular formulae. One is C5H10 and the other is C5H12.
You have to distinguish which compound, X or Y, is saturated.

You hypothesise that compound X is saturated.

X C5H12. Y C5H10.

8.1 Design an investigation to show that your hypothesis is true. Use the following to write down your design
(write only the question number and next to it your answer):
8.1.1 Write down your investigative question. (2)

8.1.2 Write down a list of apparatus and chemicals you will use. (2)

8.1.3 State the safety precautions that you will take. (2)

8.1.4 Write down the procedure you will follow. (4)

8.2 Describe how you will use your observations to verify your hypothesis. (2)

8.3 Write down the IUPAC name of compound Y. (2)

9.
More than 90 million organic compounds are known to man today. In the table below the letters A to E represent a
few of these compounds.
COMPOUND
A CH3 CH2 CH2 COH
II
O
B 2,5-dimethylhexane

C CH3 − CH − CH3
I
OH
D 6-methyl-1-heptene

E O CH3
II I
CH3 ‒ C ‒ CH2 ‒ CH3

9.1 Write down the IUPAC name of compound A and compound E. (2)

9.2 Write down the structural formula of compounds B and D. (4)

9.3 To which homologous series does compound E belong? (1)

9.4 Write down the IUPAC name of an isomer of compound C. (2)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 27 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
10. ( Memo Page 39 - 40 )
10.1 What functional group is contained by the ketones?

10.2 The condensed structural formula of an organic compound is shown below:

Br
I
CH ‒ CH2 ‒ CH3
I
CH3 ‒ CH2 ‒ CH2 ‒ CH ‒ CH2
I
Br

Which ONE of the following is the correct IUPAC name of this compound?

A 4,6-dibromooctane
B 4-bromo-5-bromo-5-propylpentane
C 3,5-dibromooctane
D 2-bromo-1-bromo-1-propylpentane

11.
Rubber is a naturally occurring compound. The diene, 2-methylbuta-1,3-diene, is one of the repeating units found
in rubber.
Over 20 million families depend on rubber cultivation for their livelihood. Tens of thousands of hectares of tropical
forests have been cleared to make way for rubber plantations.

Chemists have been able to combine other dienes to obtain synthetic rubbers. Some rubber products include latex
products such as hand gloves, raincoats and other products used in the battle against HIV/Aids.

The world’s largest use of rubber is in tyres, and most tyres contain both natural rubber, which withstands heat
better, and one or more kinds of synthetic rubber.

11.1 Is 2-methylbuta-1,3-diene an example of a saturated or an unsaturated hydrocarbon?

Write down a reason for your answer. (3)

11.2 Write down the structural formula of 2-methylbuta-1,3-diene. (2)

11.3 With regard to the environment, name TWO disadvantages of rubber and the production of rubber. (2)

11.4 With regard to human life, name TWO benefits of rubber and the production of rubber. (2)
12.
12.1 Write down the name of a group of organic compounds with the carbonyl group as functional group.
12.2 The structural formula of an ester is shown below.
H H H H O H H
I I I I II I I
H–C–C–C–C–O–C–C–C–H
I I I I I I
H H H H H H
Which ONE of the following pairs of compounds can be used to prepare the above ester?
A Propanoic acid and butan-1-ol
B Propanoic acid and butan-2-ol
C Butanoic acid and propan-1-ol
D Butanoic acid and propan-2-ol

12.3 The structural formula for a commonly used CFC is given below.
F
I
Cℓ – C – F
I
Cℓ
Write down the IUPAC name for this CFC.
12.4  Write down a structural formula of an isomer of 2-methylpropane.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 28 of 107
 Organic Chemistry Naming and Structures Past Matric Papers
13.1 Ethanol is an example of a secondary alcohol that is completely soluble in water. ( Memo Page 40)
Correct this statement.
13.2 Which ONE of the following compounds has structural isomers?

A H H B H H C Cℓ Cℓ D H Br
I I I I I I I I
Cℓ ‒ C ‒ C ‒ H Br‒ C ‒ C ‒ H Cℓ ‒ C ‒ C ‒ H H‒C‒C‒H
I I I I I I I I
H H H H Cℓ Cℓ Br H

13.3 Consider the following terms and compounds in organic chemistry.

aldehydes ketones oxidation haloalkanes hydrolysis

ethyne hydrohalogenation but-1-ene water

hydration chlorine butane potassium hydroxide alkynes

Choose from the above terms and compounds: (Write down the question number only and next to each the correct
term or compound.)
13.3.1 The homologous series that has a carbonyl group as functional group (1)
13.3.2 A saturated hydrocarbon (1)

13.3.3 The homologous series to which propanal belongs (1)

13.3.4 The homologous series to which 2-bromobutane belongs (1)

13.3.5 An unsaturated compound that has isomers (1)

13.3.6 A compound which belongs to the homologous series with the general formula CnH2n – 2 (1)

14.1 Write down the structural formula for 2,2,4-trimethylpentane. (2)

14.2 Name the homologous series to which H – C ≡ C – H belongs

14.3 Which ONE of the following compounds represents a ketone?

A H H B H
I I I
H — C —C —C—H H –C – O –C –H
I II I II I
H O H O H

C H D H
I I
H – O – C – C –H H – C –O – H
II I I
O H H

14.4 Consider the compound with molecular formula C4H10.

How many structural isomers does this compound have?

A 1 B 2 C 3 D 4

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 Organic Chemistry Naming and Structures Past Matric Papers
14.5 ( Memo Page 40 - 41 )
Which ONE of the following is the functional group of aldehydes?

A ─ COO ─

B ─ COOH

C ─ CHO

D ─ OH
15.
The chemical properties of organic compounds are determined by their functional groups.
The letters A to F in the table below represent six organic compounds.

A H H H H B H C H
I I I I I I
C = C – C – C–H H–C–H H–C–H
I I I H H H H H H H
H H H I I I I I I I
H–C–C– C –H H–C –C–C–C–C–C–H
I I I I I I I I
Br H H H H H H H

H–C –H
D Methanal I
H
E
H O
I II
H–C –C–O–H
I
H

F Methyl methanoate

15.1 Write down the LETTER that represents the following:
15.1.1 An alkene (1)
15.1.2 An aldehyde (1)

15.2 Write down the IUPAC name of the following:

15.2.1 Compound B (2)
15.2.2 Compound C (2)
15.3 Write down the structural formula of compound D. (2)
15.4 Write down the IUPC name of the carboxylic acid shown in the table. (2)
15.5 Write down the structural formula of compound F. (2)

16.
Five alcohols represented by the letters A – E are listed in the table below

A Methanol B Ethanol C Propan-1-ol

D Butan-2-ol E methylpropan-2-ol

16.1 Which ONE of the above alcohols is SECONDARY alcohol?
Write down only the LETTER that represents the alcohol. (1)

16.2 The letter E represents methylpropan-2-ol. For this alcohol, write down the following:
16.2.1 Its structural formula (2)
16.2.2 The LETTER in the table that represents one of its structural isomers. (1)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers Page 30 of 107
 Organic Chemistry Activities 1 Naming and Formulae Memorandum
1. ( Questions on Page 20 )
1.1 Organic molecules are molecules containing carbon atoms.
1.2 Hydrocarbons are organic compounds that consist of hydrogen and carbon only.
2. 2.2 2.3
2.1 H H H H
CH3 CH2 CH2 CH3 OR CH3 ( CH2 )2 CH3 C 4 H 10
H C C C C H

H H H H
3.
3.1 normal or unbranched or straight -chain alkanes.

3.2 H H H 3.3 CH3 CH2 CH2 CH2 CH2 CH3 3.4

C 8 H 18
H C C C H
OR CH3 (CH2 )4 CH3
H H H
4.
4.1 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.
4.2 Condensed structural formula notation shows the way in which atoms are bonded together in a
molecule but does not show all bond lines.
4.3 Molecular formula is a chemical formula that indicates the type of atoms and the correct number of
each in a molecule.
4.4 Saturated compounds are compounds in which there are no multiple bonds between C atoms in
their hydrocarbon chains.
4.5 Unsaturated compounds are compounds with one or more multiple bonds between C atoms in
their hydrocarbon chains.

5.
5.1 Cn H2n + 2 5.2 7 5.3 unreactive 5.4 well 5.5 little 5.6 are
6.
6.1.1 6.1.2 6.1.3
H H H H H H H H H H
H C C C C C C H H C C C H H C H
H H H H H H H H H H

6.2.2 CH3 CH2 CH3 6.2.3 CH4

6.2.1 CH3 (CH2)4 CH3

6.3.1 C6 H14 6.3.1 C3 H8 6.3.3 CH4

7.
7.1.1 7.1.2 7.1.3
H H H H H H H H H H H H H H H
H C C C C C C H H C C C H H C C C C C C H
H H H H H H H H H
7.2.1 CH3 (CH)2 (CH2)2 CH3
7.2.2 CH2 CH CH3 7.2.3 CH3 CH2 (CH)2 CH2 CH3
7.3.1 C6 H12 7.3.2 C3 H6 7.3.3 C6 H12

7.1.4 H
H H H H
H C C C C C H 7.2.4 CH2 CH (CH2)2 CH3 7.3.4 C5 H10
H H H
8.
Add the alkane cyclohexane to bromine water. No change in colour occurs for a long time, thus no obvious reaction.
Add the alkene cyclohexene to bromine water, The colour immediately disappears. A very quick reaction occurred.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 MEMORANDUM Page 31 of 107
 Organic Chemistry Activities 1 Naming and Formulae Memorandum
( Questions on Page 20 - 21 )
9.1.1 H H H H 9.1.2 H

H C C C C C C H H C C C H
H H H H H
H
9.1.3 H H H H 9.1.4 H H H
H C C C C C C H H C C C C C H
H H H H H H H
9.2.1 CH3 C2 (CH2)2 CH3 9.2.2 CH C CH3 9.2.3 CH3 CH2 C2 CH2 CH3 9.2.4 CH C (CH2)2 CH3

9.3.1 C6 H10 9.3.2 C3 H4 9.3.3 C6 H10 9.3.4 C5 H8

10.1 A functional group is a bond or an atom or a group of atoms that determine(s) the physical and chemical
properties of a group of organic compounds.
10.2 Homologous series are 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.
11.1 Cn H2n 11.2 Cn H2n ‒ 2

12.1 trichloromethane 12.2 1,2-dichloro-1-fluoroethane 12.3 bromodifluoromethane

12.4 1,2-dichloroethene 12.5 1,3-dibromo-1-chloropropane 12.6 1,2-dibromopropene
12.7 1-bromo-2-chloro-1-iodoethane 12.8 2-bromopropene 12.3 3-bromopent-1-yne
13.
13.1 13.2 13.3
H Cℓ H H H H H I Cℓ H H F F H H Cℓ H
H C C C C C C H H C C C C C H H C C C C C C H
H H H H H H H H H H H H H H H
14.
14.1 H 14.2 H H
H C H H C H H C H
H H H H H H H H H H
H C C C C C H H C C C C C C C C H
H H Br H H H H H H H H H H
14.3
H
H C H
H H H H

H C C C C C C H
H H H H H
15.1 4-methylpent-2-yne ( triple bond has preference over a substituent )

15.2 2,3-dibromo-5-methylheptane

15.3 1,1-dibromo-2,3-dimethylbut-2-ene
16.
16.1 Structural isomers are organic molecules with the same molecular formula but different structural formulae.
16.2 Positional isomers have the same molecular formula but different positions of the side chain, substituents or
functional groups on the parent chain.
17.
CH3 Br 17.2 2-bromo-5,5-dimethyloctane
17.1 4-bromo-3-ethyl-2-methylhexane
I I
CH3 CH CH CH CH2 CH3
I
C 2H 5

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 MEMORANDUM Page 32 of 107
 Organic Chemistry Activities 1 Naming and Formulae Memorandum
18. ( Questions on Page 21 - 22 )
18.1 Homologous series are 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.
18.2.1 butan-1-ol 18.2.2 butan-2-ol 18.2.3 hexan-3-ol

18.3.1 B H 18.3.2 18.3.3 A

C H
H O H H H H
H O H
C C H
H C H H C C C O
H C C C H
H H H H H
H C H H H H

19. H
19.1 19.2 19.3 H
H H H H H H H H O H H
H
H H
H C O H C C C C O H C C C C C C C H

H H H H H H H H H H H H

20.
20.1 20.2 H O 20.3
H H H O
O H H
H C C O H C C C C O
H
H C O H H H H
21.
21.1 propanoic acid 21.2 pentanoic acid
22.
22.1 butyl propanoate 22.2 methyl propanoate 22.3 ethyl propanoate
23.
23.1 O H 23.2 O
H H H propanoic acid
H C O C C H H O C C C H functional isomer
H H H H
23.3
H O H H H H H O H H O H H
H H
H C C C C C H H C C C C C H H C
C C C C H
H H H H H H H H H H
H H
pentan-2-one pentan-3-one pentanal
positional isomer functional isomer
24.
24.1 Functional isomers have the same molecular formula, but different functional groups.
24.2 Positional isomers have the same molecular formula but different positions of the side chain, substituents or
functional groups on the parent chain.
25.
25.1 butanone 25.2 butanone 25.3 propanone 25.4 octan-3-one 25.5 hexan-2-one
25.6 propanal 25.7 pentan-2-one 25.8 pentan-3-one 25.9 ethanal 25.10 butanal
25.11 hexanal
26.
26.1 26.2 26.3
H H O H H
H H H O H H H H H H H O H H
H C C C C C H H C C C H C C C
C C C C C H C C C H
H H H H H H H H H H H H
H H H H
pentan-3-one
octan-4-one ( numbered from the left ) hexan-3-one

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 Organic Chemistry Activities 1 Naming and Formulae Memorandum
26.4 26.5 ( Questions on Page 22 - 23 )
H H H O H H H H H O

H C C C C H H C C C C C C H

H H H H H H H H
butanal hexanal
27.
27.1 Functional isomers have the same molecular formula, but different functional groups.
27.2 Positional isomers have the same molecular formula but different positions of the side chain, substitu-
ents or functional groups on the parent chain.
27.3 Chain isomers have the same molecular formula but different types of chains.
28.
Write down the names and structural formulae and molecular formulae for two positional isomers of
28.1 hex-1-ene. 28.2 pentan-2-ol 28.3 1,2-dibromopropane

H H H H H H C5H12O Br Br H
H
C C C C C C H H C C C H
H O H H H
H H H H H H H H
H C C C C C H
C6 H12 C3H6Br2
H H H H H
Br H Br
H H H H H H H
H C C C H
H C C C C C C H O H H H H
H H H
H H H H
H C C C C C H 1,3-dibromopropane
hex-2-ene C6 H12 H C3H6Br2
H H H H
pentan-1-ol C5H12O
H H Br
H H H H H H
H
H C C C Br
H C C C C C C H
H H O H H H H H
H H H H 1,1-dibromopropane
H C C C C C H
hex-3-ene C6 H12
H H H H H H Br H
pentan-3-ol C5H12O
H C C C H
28.4 hex-2-yne
28.5 H Br H
H H H H 2-bromo-2-chloropropane C3H6 Br Cℓ 2,2-dibromopropane
H Cℓ H C3H6Br2
H C C C C C C H
H H H H H C C C H
C6 H12 H Br H 28.6 hept-2-one C7 H14 O
2-bromo-1-chloropropane
H O H H H H H
hex-3-yne Cℓ Br H
H C C C C C C C H
H H H H H C C C H
H H H H H H
H C C C C C C H H H H
H H H H 28.6 hept-4-one
1-bromo-3-chloropropane
Cℓ H Br
H H H O H H H
Cℓ H C C C H H C C C C C C C H
H H
H H H H H H H H H
Br C C C H
H H H 1-bromo-1-chloropropane

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 MEMORANDUM Page 34 of 107
 Organic Chemistry Activities 1 Naming and Formulae Memorandum
29. 2-methylheptane H ( Questions on Page 23 )
3-methylheptane
H
H C H
H C H H H H H H
H
H H H H H H H C C C C C C C H
H C C C C C C C H H H H H H H H
H H H H H H H CH3CH2CH(CH3) (CH2)3CH3
CH3CH(CH3) (CH2)4CH3
H 4-methylheptane
H C H
H H H H H H
H C C C C C C C H
H H H H H H H CH3(CH2)2CH(CH3) (CH2)2CH3

30. 30.2
30.1
H H H H O
H H H O
H H C C C C H
C
H C C C C O
H H H H H H H
buttanoic acid pentanal

C4 H8 O2 C5H10O

31.
Alkanes, carboxylic acids and aldehydes H H
32. H H
C H C H
H H H H H H H H H H H H H H
H C C C C C C H H C C C C C H H C C C C C H
H H H H H H H H H H H H H H H H
hexane 2-methylpentane 3-methylpentane
H
H
H C H
H C H
H H H
H H H
H C C C C H
H C C C C H
H H H
H C H H H H
H C H
H
2,2-dimethylbutane H 2,3-dimethylbutane

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 MEMORANDUM Page 35 of 107
 Organic Chemistry Activities 1 Naming and Formulae Memorandum

33.
33.1 3-methylheptane

33.2 1-bromo-1,1-dichloro-4-ethyl-3,7-dimethyloctane

34.
34.1 H 34.2 H 34.3 H
H C H H C H H C H
H H H H H C H
H C C C H H C C C H H Br H H H Br H
H H H Cℓ H H C C C H
C C C C C
H C H
2-chloromethylpropane
H Cℓ H H H H H
H
H C H
dimethylpropane
H

2,7-dibromo-2-chloro-4-ethyl-5-methyloctane

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Activities 1 MEMORANDUM Page 36 of 107
 Organic Chemistry Naming and Structures
MEMORANDUM Past Matric Papers
1.1 alkynes ( Questions on Page 24 - 25 )
1.2.1 O 1.2.2 O
II II
‒C‒ ‒C‒H
1.3 C The carbonyl group is the functional group for ketones
1.4 A
2.1 Alcohols are flammable.
H
2.2.1 H H H H O H
I I I I I I
H‒C‒C‒C‒O‒H H‒C‒C‒C‒H
I I I I I I
H H H H H H
propan-1-ol propan-2-ol

2.2.2 propan-1-ol

2.2.3 The position of the OH-group in the chain will affect the intermolecular forces.

2.3.1 The boiling point of the alcohols will increase with molecular mass.
The larger the molecular mass of a member of the same homologous series of alcohols, the higher the
boiling point.

[Independent (Molar mass), dependant (Boiling point)]

2.3.2 Don’t heat alcohols over an open flame

2.3.3 Measuring cylinder

Thermometer
8 containers e.g. test-tubes or beakers or flasks.
Heat source e.g. Hot plate

2.3.4 Measure equal volumes of the eight alcohols and transfer it to separate containers.
Heat samples of each compound in a water bath until it boils.
Measure the temperature with a thermometer at boiling point.
3.1 A H O This is the shortest ester chain.
I II C2H4O2
H–C–O–C–H Add CH2 to get the next member
I C3H6O2
H
3.2 Cyclohexane
3.3 O
II
‒C‒
3.4 B Each molecule must have 6 carbon atoms
4.1 ‒C‒ 4.2 O
II II
O pentan-2-one CH3 ― CH2 ― CH2 ― C ― O ― CH2 ― CH3
4.3 structural isomers

4.4 H O H
I II I
H‒C‒C‒C‒H propanone
I I
H H
4.5 B

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers MEMORANDUM Page 37 of 107
 Organic Chemistry Past Matric Papers Naming and Formulae Memorandum
5. ( Questions on Page 25 - 27 )
5.1 ethanal– aldehydes
ethanoic acid– carboxylic acids
5.2 H O
I II
H‒C‒C‒H
I
H
5.3 These medicines contain alcohol either as a preservative or as a germicide ( to kill germs ). Any additional
intake of alcohol will increase the blood alcohol level which may lead to either loss of coordination or severe
intoxication.
6.1 4,4-dimethylhexan-2-one
6.2 CH3 CH3
I I
CH3 CH CH CH3 or CH3 C CH2 CH3
I I
CH3 CH3
6.3 A ( maximum number of H atoms )
7.
7.1 Functional group
7.2 D Aromatics have a ring structure
7.3 True
7.4 B
7.5 Functional group
7.6 ethanol C2H5OH
8.
8.1.1
Investigative question:
Which one of the two compounds (X and Y) is saturated?
TEST FOR SATURATION USING BROMINE / IODINE
8.1.2
Apparatus and chemicals:
Bromine water solution Br2 or iodine solution I 2
Test tubes, medicine dropper
8.1.3
Safety precautions:
• Protective clothing : Use gloves to avoid contact with skin. Use goggles to protect eyes.
Wear a laboratory coat to protect clothing.
• Work in fume cupboard and wear a mask or work in a well ventilated room or work outside. Don’t inhale fumes.
• No open flames to ignite the fumes
8.1.4
Procedure:
• With a dropper, add the bromine water or iodine solution to each of the compounds X and Y in the test tubes
• Observe, compare and record the rate of colour change or decolourisation for the two compounds.
OR BOILING POINT METHOD
8.1.2
Apparatus and chemicals
Water bath, Heat source, Retort stand, Thermometer
8.1.3 Safety precautions:
• Protective clothing : Use gloves. Avoid contact with skin. Goggles.
• Work in fume cupboard. Wear a mask. Work in a well ventilated room or work outside. Do not inhale fumes.
• No open flames
8.1.4
Procedure:
• Set up the apparatus with the thermometer in the water bath
• Place the test tubes containing the liquids in the water bath
• Heat waterbath gently until the each liquid boils
• Record/compare the temperature at which the solutions boil

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers MEMORANDUM Page 38 of 107
 Organic Chemistry Past Matric Papers Naming and Formulae Memorandum
( Questions on Page 27 - 28 )
8.2 SATURATION TEST
The solution that shows a rapid colour change is unsaturated.
OR
The solution that shows no or a slow rate of colour change (no reaction takes place) is saturated
BOILING POINT METHOD
The solution which has the higher boiling point is saturated ( having more H atoms it has a greater molar mass and
thus stronger intermolecular Van der Waals forces ).
OR
The solution with the lower boiling point is unsaturated

8.3 ( Any one )

pent-1-ene OR pent-2-ene OR 3-methylbut-1-ene
OR 2-methylbut-1-ene OR 2-methylbut-2-ene
9.
9.1 A : Butanoic acid E : methylbutanone
9.2
B D
H
H I
H
I H‒C‒H
I
H‒C‒H H‒C‒H
H H H H H H
I I I I I
H H H H
C=C‒C‒C‒C‒C‒C‒H
I I I I
I I I I I
H‒C‒C‒C‒C‒C‒C‒H
H H H H H H
I I I I I I
H H H H H H

9.3 Ketones
9.4 propan-1-ol

10.
10.1 Carbonyl group
10.2 C

11.
11.1 Unsaturated
Not all C ‒ C bonds are single bonds as it contains C ‒ C double bonds.
11.2 H H H
I I I
H‒C=C‒C=C‒H
I
H‒C‒H
I
H

11.3 Any TWO:

• Destruction of indigenous forests, leading to global warming
• Rubber is not biodegradable – disposal impacts negatively on environment
• Burning of rubber releases toxic gases
11.4 Any TWO:
• Job creation
• Tyres for cars / gloves for medical industry / raincoats etc.
• Protective devices – insulation

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers MEMORANDUM Page 39 of 107
 Organic Chemistry Past Matric Papers Naming and Formulae Memorandum
12. ( Questions on Page 28 - 30 )
12.1 Ketones O
II
‒C‒
12.2 A
12.3 Dichlorodifluoromethane
12.4 H H H H
I I I I
H–C–C–C–C–H
I I I I
H H H H

13.1 primary alcohol

13.2 D H Br Br H
I I I I
H‒C‒C‒H H‒C‒C‒H
I I I I
Br H Br H

1,2-dibromoethane 1,1-dibromoethane
13.3.1 O
II
carbonyl group ‒ C ‒ ketone
13.3.2 butane ( all single bonds, C is surrounded by the maximum number of H atoms )

13.3.3 aldehydes
13.3.4 haloalkanes
13.3.5 H H H H H H H H
\ I I I I I I I
but-1-ene C=C– C– C – H and but-2-ene H– C– C=C– C–H
/ I I I I
H H H H H
13.3.6 ethyne ( alkynes )
14.1 H H
│ │
H H—C—H H H—C—H H
│ │ │ │ │
H — C — C — C — C — C — H
│ │ │ │ │
H H—C—H H H H
│
H
14.2 Alkynes

14.3 A
14.4 B butane, methylpropane
H H H H H H H
I I I I I I I
H‒C‒C‒C‒C‒H and H‒C‒C‒C‒H
I I I I I I
H H H H H H
H‒C‒H
I
H

14.5 C The oxygen atom is attached to an end C atom in an aldehyde.

There is also a H atom attached to the end C atom.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers MEMORANDUM Page 40 of 107
 Organic Chemistry Past Matric Papers Naming and Formulae Memorandum
15.1.1 A ( Questions on Page 30 )
15.1.2 D
15.2 15.2.1 1–bromo-2-methylpropane ( the 2 is not necessary )
15.2.2. 2,4–dimethylhexane

15.3 O functional group must be encircled

II
H – C– H

15.4 ethanoic acid

15.5
H O
I II
H–C–O–C–H
I
H
16.1 D H H H H
I I I I
H‒C‒C‒C‒C‒H Secondary : OH is attached to a C atom that is bonded to two other C atoms
I I I
H H H
O
H

16.2 .1 H Tertiary : OH is attached to a C atom that is bonded to three other C atoms

I
H‒C‒H 2-methylpropan-2-ol
H H
I I
H‒ C C C ‒H
I I I
H O H
H

16.2.2 D

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Naming and Formulae Past Matric Papers MEMORANDUM Page 41 of 107
 TOPIC : Organic Molecules - Structure and Physical properties NOTES
Electronegativity is the ability of an atom in a covalent bond to attract electrons to itself.
Polar Covalent bonds form a continuum of electron pulling abilities ( ionic ) on shared ( covalent ) electron pairs.
Thus all bonds between different atoms have covalent and ionic character.
Pure covalent bonds form between identical atoms.
Electrons shared evenly between two atoms. The two atoms form a neutral molecule.
I I
I I

Non-polar molecule.
Non-polar bonds only exist between identical atoms in a diatomic molecule.
eg. I ‒ I or I 2
Difference in electronegativity ∆EN = 2,8 ‒ 2,8 = 0 Non-polar bond
Electronegativity values are given on the periodic table : O = 3,5, C = 2,5, H = 2,1
Any two different atoms will have an uneven sharing of electrons and thus form a polar covalent bond.

Difference in electronegativity scale, ∆EN :

This illustrates what the bonds look like between the atoms.
Polar covalent

uneven sharing of electrons between different atoms

ΔEN = 2,5 ‒ 2,1 = 0,5

ΔEN = 3,5 ‒ 2,1 = 1,4
C H O H

polar covalent bond

very weakly polar covalent bond

0 ΔEN < 1 1 ΔEN > 1 2,1

C has a slightly stronger pull on O has a much stronger pull on the
the shared electron pair than H. shared electron pair than H.
“Bonds” form inside a molecule between atoms : strong bonds
weak bonds
+ A dipole.

Non-polar molecule.
δ‒ δ+ Polar molecule.
The charge distribution in C - H bonds cannot be completely
symmetrical, but the resultant bond polarity is Slight positive and negative charges
generally regarded as trivially small. at the poles are noticeable.
Ignore these slight positive and negative charges at the A dipole is a polarised molecule that has partial
poles. ( slight ) positive and negative charges.
Regard the molecule as if it has no polarity. Hence in Dipole-dipole forces form between polar
hydrocarbons the description non-polar is applied. molecules.
Intermolecular forces form outside molecules, between the different molecules
All molecules form very weak London dispersion forces between molecules.
London dispersion forces always exist between
non-polar hydrocarbon molecules.

Van der Waals forces are a category or collection of intermolecular forces.

These forces are identified as the stronger dipole-dipole forces and the weaker London dispersion forces
( which are instantaneous dipole - induced dipole forces and induced dipole-induced dipole forces ).

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 42 of 107
 Organic Molecules - Structure and Physical properties NOTES
Larger non-polar molecules form stronger London dispersion forces between molecules.
Larger molecules cause London dispersion forces to accumulate their strength and become stronger.
Gases
Weak London dispersion forces exist between small non-polar molecules.
Thus small alkane molecules CH4, C2H6, C3H8 and C4H10 are gases at 25ºC.
burning butane gas

methane gas CH4

natural gas

Liquids The weak London dispersion forces depend on the surface area of the non-polar molecule.
Increasing the length of the chain increases the surface area of the molecule.
Then individual molecules can attract each other better.

The strength of the London dispersion forces is proportional to the surface area of the molecules.

C5H12 is a liquid. Carbon chains that range in length from 5 to 20 carbon atoms
tend to be liquids.

benzine petrol

C5 H12 C8 H18

Hydrocarbons, in the liquid state, are held together by London dispersion forces.
Solids
When more than 20 carbon atoms join in a chain, then a solid like candle wax can form.

Hydrocarbons are made from hydrogen and carbon atoms.

Solid wax Mr(C23H48) = 324

London dispersion forces

As the non-polar hydrocarbon chains get even longer, there are many regions where they can line up alongside
each other. The weak London dispersion forces accumulate their strength to exert a noticeable attractive effect.
As the chain length increases even further these longer molecules become
wrapped around each other and get tangled up like strands of spaghetti.
Much more energy is then needed to separate them compared to the
short chain molecules that only had weak attractive forces between them.

Thus their boiling points increase with chain length.

Bitumen has long hydrocarbon chains and must be heated above 400ºC before
it melts. Thus these accumulated London dispersion forces are relatively strong. tangled long chain molecules

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 43 of 107
 Organic Molecules - Structure and Physical properties NOTES
TOPIC Physical properties of saturated hydrocarbons depend on the structure of the molecule
Eg. the chain length
Boiling points ( BP ) indicate the strength of the forces between molecules.
The stronger the molecules stick together, the more energy it will take to rip them apart and blast them off into the
atmosphere as separated gas molecules.
Boiling points of the saturated hydrocarbons, or Alkanes.
boiling points of alkanes
Name Forrmula Boiling Point (oC)
boiling point ( °C )
methane CH4 ‒161
butane C4H10
ethane C2H6 ‒89 0
propane C3H8 ‒42
butane C4H10 0
BP < 25ºC means they have
already boiled and are thus gases. – 42
propane C H
3 8
BP > 25ºC means they are still liquids as
they have not yet begun to boil and move
apart to form gases – 89 ethane C2H6

pentane C5H12 36
hexane C6H14 69
heptane C7H16 98
methane CH
octane C8H18 125 – 161 4
molar mass ( g )

16 30 44 58
Increasing molecular masses means adding more carbon atoms in the chain. This increases the number of
electrons. This increased electron density thus increases the number of positive and negative contact points
which increases the strength of the London dispersion intermolecular forces.
Bigger molecules have more electrons, so more distortion of the electron cloud occurs and more points of
contact form, requiring more energy to snap these bonds. Thus they have a higher boiling point.
London dispersion forces are forces of attraction between fluctuating dipoles in atoms and molecules that are
close together.
Boiling point ( ºC )
Boiling points ( BP ) increase more uniformly with
120
increasing chain length than melting points.
In boiling points, all the bonds have to break to 100
form freely-moving gas molecules so the situation is much
80
simpler.
In melting points, ( MP ) only some of the bonds 60
break to enable molecules to slide past each other.
40
The bonds that do not break can cause complications.
Example : 20
Solid ethane forms rectangular plates in layers that are 0
closely packed. The atoms are close and strongly bonded.
Solid butane forms hexagonal plates with bigger atoms ‒20
that are also closely packed in layers. ‒40
‒60
‒80
‒100
solid ethane solid propane solid butane
‒120
MP = ‒182,8ºC MP = ‒190ºC MP = ‒138ºC
‒140
In between is solid propane which forms five-sided plates ‒160
that cannot pack closely together. Thus the solid
molecules are further apart and more weakly held 1 2 3 4 5 6 7 8
together which explains its lower melting point. number of C-atoms in chain

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 44 of 107
 Organic Molecules - Structure and Physical properties NOTES
Instantaneous dipole
• •
At any moment the valence electrons in a molecule or atom may be spread out uniformly so that
• • •
there is no charge concentration to produce a dipole as the electron cloud is perfectly symmetrical. •

But this electron cloud will not be perfectly symmetrical at all times.
Because the electrons are constantly moving and swirl around the nucleus in a random
manner, one instant later they will be accidently bunched up in some region, distorting the • • ∂+
electron cloud and producing a slight partial negative charge there. Another region of the atom ∂– • ••
•
or molecule will then have a thinned out region of the electron cloud which allows a slight partial
positive charge from the nucleus to be manifest there.
Thus a temporary dipole has been set up.
As soon as this dipole forms, it disappears in an instant as the electrons swirl to another
position in the molecule where they accidently bunch up, perhaps in different numbers, causing ∂+ •
an uneven distribution of charge that forms another fluctuating transient dipole that •
• • ∂–
lasts for an instant. ••
Bigger molecules have more electrons and a bigger space for the
electrons to move around in and whenever the electrons randomly ∂– ∂+ ∂+
concentrate for an instant they form more asymmetrical points where •• • • •
temporary or instantaneous dipoles appear for an instant. • • • • • •
• • •• • • •
∂+ ∂– ∂–
This accidental concentration of negative charge briefly in one section of the atom or molecule momentarily flickers
on and off randomly as the electrons move around distorting the charge distribution in other sections of the same
particle.
Induced dipole
A temporary unsymmetrical distribution of electrons in one part of the atom or molecule
induces the opposite polarity in another part of the same molecule.

Instantaneous dipole - induced dipole forces

( This is a London dispersion force )
Consider two non-polar molecules that happen to move close together.
instantaneous dipole
∂– ∂+ ∂+
•
• • • •
• • •• •• Random electron movements in the one molecule will produce an
• • •• • instantaneous dipole.
∂+ ∂– ∂–
∂– ∂+ ∂+
The
imm se sli ••••• •
g
cha ediat ht pa • •
mo rge in ely ind rtial c
••• •• • •• instantaneous dipole
lec h ∂+ ∂–
ule the n uce t arge ∂–
. ear he sw ∂+
by o i ∂– ∂+
neu ppos ll
tral ite ••• ••
• ••• • • • •• induced dipole
A temporary or instantaneous dipole can create temporary dipoles.
Bunched up electrons in the instantaneous dipole repel electrons in the induced dipole and are thus attracted to
the positive nuclei of the induced dipole. The small partial negative charge and the little bit of induced positive
charge cause a brief attraction between the molecules. These opposite charges remain synchronised.
This attractive force only lasts for an instant and is then gone.
Thus an instantaneous induced dipole was formed.
These attractions are able to form between between molecules with no permanent dipoles.
This instantaneous dipole - induced dipole force exists between all molecules and atoms.

Induced dipole - induced dipole forces are caused by two non-polar molecules colliding and thus
mutually distorting their electron clouds to simultaneously form induced dipoles in both the molecules.
Electrons from both
Two non-polar molecules collide molecules get too close
• • • • • ∂–
∂– • • • ∂+ ∂+ • • and repel each other
• • creating temporary dipoles
( This is a London dispersion force )

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 45 of 107
 Organic Molecules - Structure and Physical properties NOTES
Dipole - dipole forces between permanent dipoles
London dispersion forces depend on the temporary movement of electrons in the molecules
Cℓ .Atoms with a high electronegativity ( the ability to pull hard on the shared electrons in the bond )
I such as chlorine, Cℓ, create a more polar molecule where the electrons are more tightly held.
H‒C‒H The electrons are unable to move around as freely as before and this reduces the effect
I of the London dispersion forces.
H At least one atom must be present with a significantly different electronegativity.
Cℓ ∂–
Cℓ Cℓ has a stronger pull on the electrons in the molecule and this “traps” some
• •• of the electrons in the vicinity of the Cℓ atom.
•
These electrons spend more time in the vicinity of the Cℓ atom, giving it a
slightly negative charge.
∂+ The molecule is now polar as it always has a permanent dipole.
Holding the electrons in more of a “fixed” position will produce a dipole.
A partial charge within a molecule forms due to the uneven distribution of the electrons.
Thus the dipole- dipole forces create an additional bond between polar molecules.

For convenience, we draw a simplified dipole as δ‒ δ+ or +

Alkanes Haloalkanes
Weak London dispersion forces. The dipole-dipole forces are stronger than the
weak London dispersion forces.
dipole-dipole forces
+
+ +

+
+ +

These dipoles also have London dispersion

forces between their molecules in addition to their
dipole - dipole forces.

The boiling point of polar molecules is usually higher than that of similar non-polar hydrocarbon molecules
because polar molecules form a dipole, and thus their intermolecular forces consist of both dipole-dipole forces
and London dispersion forces. Thus it takes more energy ( a higher temperature ) to break these stronger bonds.
boiling point ( °C ) haloalkanes

90
C4H9Cℓ ( 78 ºC )

40 alkanes C3H7Cℓ ( 47 ºC )
C4H10 C2H5Cℓ ( 12 ºC )
‒ 10

C 3H 8 CH3Cℓ (‒24 ºC )
– 60
C 2H 6
‒ 110

CH4
– 160
molar mass ( g )
16 30 44 58 100 72 86
The chlorine atom makes the haloalkane molecule bigger than the corresponding alkane molecule.
Bigger molecules experience stronger London dispersion forces.
The haloalkanes are polar and have dipole-dipole forces in addition to their London dispersion forces.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 46 of 107
 Organic Molecules - Structure and Physical properties NOTES
Ketones and Aldehydes form Polar Molecules
Ketone and aldehyde molecules cannot form hydrogen bonds as they have no OH functional group.
The oxygen atom, with its big electronegativity of 3,5 attracts the bonding electrons and forms a stronger
permanent dipole with the oxygen atom having a negative polarity. This produces a bigger partial charge δ‒ and
makes a strongly polar molecule that produces stronger dipole-dipole attractions.
O δ‒ O δ‒
δ+ δ‒
II II
CH2 Cℓ
C C
H 3C H
δ+ H 3C
H 3C δ+ CH3 CH2

Chlorine has less electronegativitry ( 3 ) and attracts the bonding pair of electrons with less energy and produces
a smaller partial charge δ‒. This makes a less polar molecule that produces weaker dipole-dipole attractions.
ketone aldehyde haloalkane
propanone Boiling point 56 ºC propanal Boiling point 46 - 50 ºC chloroethane
O Boiling point 12 ºC
O
+

+ + Cℓ

+ +
+
stronger stronger
dipole - dipole dipole - dipole weaker
attraction attraction dipole - dipole
attraction

+ +
+
The more polar ketone and aldehyde molecules have stronger dipole-dipole attractions than the less polar
haloalkane molecules.
Ketones and aldehydes have higher boiling points than haloalkanes.
NOTE
Weak London dispersion forces exist between all molecules.
In addition, there are stronger dipole -dipole forces between polar molecules.
CAUTION
Do not compare ketones with aldehydes. This gets very complex.
For 3 and 4 carbon atoms, ketones have higher boiling points than aldehydes. ( butanal 75 ºC ; butanone 80 ºC )
For 5 carbon atoms they are similar. ( pentanal 102 ºC ; pentan-2-one 103 ºC and pentan-3-one 101 ºC )
For 6 carbon atoms aldehydes have higher boiling points.
( hexanal 130 ºC ; hexan-2-one 126 ºC and hexan-3-one 120 ºC )
These data do not support the conclusion that either aldehydes or ketones have higher boiling points.
The van der Waals forces represent the total intermolecular forces :
∂+ ∂– ∂+ ∂–
• dipole-dipole forces ( between two polar molecules ).

∂+ ∂– ∂–
• dipole-induced dipole forces ( O2 in water ) O2 ∂+ ∂–
∂+
O2
water becomes

• induced dipole-induced dipole ( or instantaneous dipole-induced dipole ) forces also called London dispersion
forces between non-polar molecules. Consider two neutral molecules A and B : A B
∂+ A ∂–
One molecule becomes an instantaneous dipole. B
It induces opposite charges in the neutral molecule. ∂+ A ∂– ∂+ ∂–
B
These charges form London dispersion forces.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 47 of 107
 Organic Molecules - Structure and Physical properties NOTES
Hydrogen bonds ( Van der Waals forces do not include the hydrogen bonds )
Hydrogen bonds are strong dipole-dipole forces formed by O-atoms and the H-atom in the OH group.
Consider methanol CH3OH.
Oxygen with strong electronegativity 3,5 pulls the shared pair of electrons ( which is
r inged ) away from the H-atom which only has an electronegativity of 2,1.
H ∂‒ ∂+ This leaves a small positive charge ∂+ on H. But H, with its only electron pulled
•
•
•
•

• •
H • C•O • H • away, reveals a tiny H-nucleus or proton.
The small partial positive charge ∂+ located in the very small space of the hydrogen
•
•
•
•

H nucleus produces a high charge density.

Thus H has a very large charge density which can cause a strong dipole.
lone pair of electrons Because the H-nucleus is so small, this partial positive charge can get very close to
the partial negative charge on the oxygen atom of another methanol molecule.
H ∂–

•
•
O CH3‒ O ‒ H
•
•
•
•

H •• O •• C •• H ∂+

•
•
•
•
•
•

H
hydrogen bond
hydrogen bonds
∂–
H ∂+
O CH3‒ O ‒ H
•
•
•
•

H •• C •• O •
• H
The hydrogen bond forms between an oxygen atom and the
•
•
•
•

H hydrogen atom that is in an OH hydroxyl group.

The partial positive charge ( ∂+ ) on the H-atom on one molecule is attracted electrostatically to a partial
negative charge ( ∂– ) due to a lone pair on another very electronegative oxygen atom in another molecule.
A hydrogen bond is the strongest dipole-dipole bond between molecules, and has a range of values.
But the hydrogen bond is 10 times weaker than the covalent bond that holds non-metal atoms together.
The one electron on hydrogen is held between the H-atom and the strongly electronegative O-atom that it is
bonded to. This reveals a positively charged H-nucleus on one side of the molecule and this nucleus can move
extremely close to another molecule because it has no electron orbits around it.
The electron rich strongly electronegative O-atom of the other molecule holds onto the close-up H-nucleus with a
relatively strong attraction.
Thus alcohols have higher boiling points than ketones and aldehydes.

The hydrogen bonds are the strongest intermolecular forces and require the most thermal energy to break them.
Thus a higher temperature is needed to provide sufficient thermal energy.
Carboxylic acids
Carboxylic acids have higher boiling points than alcohols that have a similar molar mass.
Carboxylic acids have two oxygen atoms and thus two sites to produce hydrogen bonds.
O can only form a hydrogen bond with an H in an OH hydroxyl group.
A pure carboxylic acid can, in addition, form dimers ( two molecules of acid bonded to each other ).
This immediately doubles the size of the molecule and so increases the London dispersion forces between one of
these dimers and its neighbouring dimers, resulting in a high boiling point.
O H‒O ethanoic acid dimer
CH3‒ C dimer C ‒ CH3 dimer
ethanoic acid ethanoic acid
O‒H O

hydrogen bonds hydrogen bonds

Each dimer acts as a bigger
molecule and as such has dimer A carboxylic acid contains two oxygen
even stronger London atoms and has two sites for hydrogen
dispersion forces between bonding. An alcohol contains only one
the dimers. This causes oxygen atom and has only one site
acids to have stronger for hydrogen bonding. More energy is
intermolecular forces. needed to overcome the hydrogen bonds
London dispersion forces dimer between the acid molecules than between
the alcohol molecules.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 48 of 107
 Organic Molecules - Structure and Physical properties NOTES
Ethanoic acid has a high boiling point 118ºC.
This O-atom ( electronegativity 3,5 ) draws the electron density from the
C-atom ( electronegativity 2,5 ).
In a sense, it also helps the other O-atom to pull on the shared pair of
electrons between the O-atom and the less electronegative ( 2,1 ) H-atom on
the right hand side.
••

H
••

O This further polarises the O–H bond, making the H-atom more positive as
I II ••
H there are effectively two O-atoms pulling on electron pair between O and H.
H‒ C O
••

C
I • • This stronger polarity creates stronger hydrogen bonds on the
H O-H site as well as a stronger dipole on the O-atom with the double bond.
The molecule is more polar due to the double bond which causes additional dipole - dipole intermolecular forces
The carboxyl group ( COOH ) of a carboxylic acid is more polar than the hydroxyl group ( OH ) of an alcohol.
Straight chains have higher boiling points than similar branched chains.
London dispersion forces are surface-area dependent.

The molecules have a larger Branched chains can have

surface area of contact, a lower boiling point due to a
and thus more delocalised smaller area of contact.
electrons, close to each other. The molecules are more
compact and cannot get
Stronger London dispersion forces too close together,
develop. resulting in weaker London
( Represented by the dotted lines ) dispersion forces.
Pentane Boiling point = 36ºC Methyl butane Boiling point = 28ºC
Dimethylpropane Boiling point = 9ºC
Branched chains have a lower boiling point due to a smaller area of contact.
As the molecules get more compact only smaller portions can get close to each other
resulting in weaker London dispersion forces.

Increased branching decreases the boiling point.

The closer a molecule is to a sphere the smaller its surface area is and the fewer
London dispersion forces operate between the molecules.
The more rod-like the molecules are eg. pentane, the better they are able to line up and bond
together.
As an analogy, macaroni is more spherical and does not stick together as strongly as the more
rod-like spaghetti does. This ability to stick together makes spaghetti tangle up and more
energy is needed to separate out the strands.
Macaroni Spaghetti
Straight chain molecules
with bigger surface areas that are in contact,
produce higher boiling points.

H
I
H‒C‒H
H H
I I
dimethylpropane 9º C H ‒ C ‒ C ‒ C ‒ H
pentane 36º C
I I
H H H H H H H
H‒C‒H I I I I I
I H‒C‒C‒ C‒C‒C‒H
H I I I I I
H H H H H

The more spherical a molecule is, the smaller area of contact it has with a neighbouring molecule. Thus the boiling
point will decrease as less energy is needed to break the intermolecular forces.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 49 of 107
 Organic Molecules - Structure and Physical properties NOTES
Melting Points
These roughly follow the trend of the boiling points. But only some of the bonds are broken when a solid melts.
The bonds that remain can cause complications.

For melting points, being spherical allows more molecules to pack together in a solid and this increases the
number of bonds in a solid volume. This raises the melting point.

Shielding of a dipole
Parts of the alkyl chain can fold around the dipole and limit the space that the functional hydroxyl group has to
react in.( the functional group is sterically hindered )

CH3 CH3
OH
O O
CH2 CH2
C
CH3CH2CH2CH2CH2OH
pentan-3-ol. Boiling point = 115ºC
pentan-1-ol. Boiling point = 137ºC
When the functional group for an alcohol is in the middle of a chain, it forms fewer hydrogen bonds with other
identical alcohol molecules.
Esters
The oxygen atom in the main chain is effectively non-polar because the difference in electronegativity acts in two
opposite directions. O
Consider methyl methanoate II
CH3 ‒ O ‒ C ‒ H
Electronegativity of O is 3,5. Electronegativity of C is 2,5. ΔEN = 3,5 ‒ 2,5 = 1 for a C = O bond.

O
H
••
••
•
•

•
•

H • C • O • •
• • • C • H
•
•

•
•

H Thus these two effects tend to cancel out. The O is non-polar.

ΔEN = 1 ΔEN = 1

O
H
••
••
•
•

•
•

H • C • O • •
• • • C • H
•
•

•
•

H
The pull on the single electron pair between O and C, is towards O.

This pull on the shared electrons also exerts some pull on the 4 electrons in the double bond, pulling them slightly
towards the C atom. Thus the partial negative charge on the O in the double bond is slightly reduced, so a
slightly weaker dipole forms.
Thus esters have a lower boiling point than aldehydes or ketones.

But the high electronegativity of the O-atom still makes an ester a stronger polar molecule than a halogen atom on
a haloalkane of similar molar mass.

The boiling points depend on the functional groups and are in this order ( from highest to lowest ) :
carboxylic acids > alcohols > ketones and aldehydes > esters > haloalkanes > hydrocarbons

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 50 of 107
 Organic Molecules - Structure and Physical properties NOTES
Hydrocarbons

For the hydrocarbons, the ranking in boiling points are, in general, as follows: Alkynes > alkanes > alkenes
Alkane Non-polar molecules form weak London dispersion forces.
London dispersion forces depend on
1. the shape of the molecule and
2. the number of electrons it contains. In addition,
3. if the electrons are loosely bonded, then they can be easily pushed around to form a stronger dipole.
We say the molecule is polarisable.
In the small atom the electrons are close to the nucleus and tightly held. It is not easy to push them around in
order that they can bunch up and form a negative pole.
Large atom with loosely
• • • • held valence electrons
small atom with tightly ∂– • •
• • • • • is more polarisable and
• held electrons. ∂+
can form a dipole.

In the large atom the valence electrons are far from the nucleus and thus loosely held. It is easier for them to move
around and bunch up for a moment to form the negative pole of a dipole.

Alkene Non-polar molecules form weak London dispersion forces.

For the same number of C atoms, boiling points are slightly lower than that of alkanes.
Each alkene has two electrons less than the alkane with the same number of C atoms.

H H H H H H H H
C= C
•
•

•
•

• • H H H
•
•
H C H

•
•
C C • C C ••
• • • H •• C
•
•

H
•
•

H
•
•

H H •
•
H H
ethane 14 electrons C 2H 6 ethene 12 electrons C 2H 4

boiling point ‒ 104 ºC

boiling point ‒ 89 ºC
CH3CH3 C H 2C H 2
Polyunsaturated margarine has many weaker double bonds and thus is softer with a lower melting point.

Alkyne Non-polar molecules form weak London dispersion forces.

Ethyne sublimes from solid to gas at ‒84ºC.

Alkyne molecules are more polarisable due to the four pi-electrons forming the second and third bond that
are loosely held.
Therefore alkynes have higher boiling points than alkanes and alkenes with the same number of C atoms in
their chains.

• •• • • ethyne or acetylene
H • C •• • C • H

H‒C≡C‒H CH CH or ( CH )2

C2 H2 e‒
e‒
two pi bonds
C-nucleus
C-nucleus + + C-nucleus

triple bond e‒
C-nucleus
e‒
Ethyne only has 10 electrons but because 4 are very loosely held in pi bonds it is easy for them to move
around and bunch up for a moment to form the negative pole of a dipole.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 51 of 107
 Organic Molecules - Structure and Physical properties NOTES
A physical change is a change in which the composition of matter is unaltered.
Boiling is a change of state from liquid to gas.
When hot liquid molecules move fast enough they can break all the liquid bonds and move far
enough apart until they are behaving like a gas.
A physical change is when a liquid molecule gains enough same molecule as a gas
energy to leave the liquid and becomes a fast moving gas
molecule that can freely move around.
The molecules are simply rearranged as they move further apart.
The gas particles have to create a bubble in which they can
freely move.
gas or vapour AP is the
atmospheric
pressure due to
the weight of all
Bubbles of gas the air above the
or vapour form liquid surface that
at the boiling AP presses down on
point of the the surface.
liquid.
liquid bubbles liquid molecules
The number of atoms or molecules does not change.

flame As a liquid the molecules are close together.

To become a gas or vapour, the molecules move
apart until each molecule is about 100 times its own
size away from its nearest neighbours.
Many gas molecules move much faster than the
speed of sound. They are supersonic. Above Mach 1.

bunsen burner When a liquid is heated, some of the liquid particles

gain enough energy to move fast enough to escape
from the liquid bonds and form a gas or vapour
bubble that rises rapidly to the surface of the liquid.

VP

bubble gas particle

VP liquid
VP liquid

Gas particles exert pressure by colliding with

the sides of the bubble. This pressure is
flame referred to as vapour pressure, VP.
It is this vapour pressure that stops the bubble from
collapsing due to the atmospheric pressure ( AP )
that presses down on the bubble.
gas or vapour escapes AP due to weight of
into the air air above surface
liquid surface
liquid
bubbles in a boiling VP
liquid

bubble
VP
VP
bunsen flame

Boiling point is the temperature at which the vapour pressure of a substance equals atmospheric pressure.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 52 of 107
 Organic Molecules - Structure and Physical properties NOTES
Evaporation
Bigger hydrocarbon molecules have stronger London dispersion forces between their molecules and
evaporate slower.
It takes more energy to snap these stronger bonds and give a bigger molecule sufficient kinetic energy to snap all
its liquid bonds to form a vapour molecule.
Hot spots form on a liquid surface where molecules gain enough thermal energy to escape from the liquid.

vapour particles evaporating

hot spot in liquid hot spot in liquid

bigger molecules smaller molecules

heptane at 25oC C7H16
pentane at 25oC C5H12

Bigger hydrocarbon molecules evaporate slower and produce less vapour.

Consider two liquids in closed containers that are both at 25ºC.

The liquid with the weakest intermolecular forces evaporates most to produce the most vapour molecules.
The more vapour molecules, the more they collide with the sides of the container to produce a higher
vapour pressure.
A liquid in a closed container will evaporate until the rate of evaporation of the liquid is equal to the rate of
condensation of the vapour.
This is called dynamic equilibrium.
At equilibrium, the visible level of liquid in each container remains constant.

less volatile more volatile

lower vapour pressure higher vapour pressure
less vapour Upward arrow indicates
rate of evaporation. more vapour
( liquid → vapour )

evaporate condense Down arrow indicates

rate of condensation
liquid
( vapour → liquid )

heptane at 25oC C7H16 pentane at 25oC C5H12

high boiling point low boiling point
98°C 36°C
Stronger intermolecular forces cause stronger bonds and less evaporation, thus a lower vapour pressure.
Weaker intermolecular forces cause weaker bonds and more evaporation occurs resulting in a higher vapour
pressure.
Vapour pressure is caused by the gas particles colliding against the sides of the container.
More vapour particles cause a higher vapour pressure ( VP ) which will soon be equal to the atmospheric
pressure ( AP ) and then the liquid will boil.
Stronger intermolecular forces produce a lower vapour pressure and need to be heated more before VP = AP.
Thus stronger forces produce a higher boiling point but a lower vapour pressure.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Page 53 of 107
 Organic Chemistry - Structure and Physical Properties Activities 2
1. ( Memo Page 62 )
Bonding forces between atoms are called ( covalent bonds / van der Waals forces ).
2.
Bonding forces between molecules are called ( covalent bonds / van der Waals forces ).
3.
Covalent bonds between atoms are much ( stronger / weaker ) than van der Waals forces between molecules.
4.
Molecules are made up by connecting................together.
5.
Two different atoms of different elements pull on the bonding pair of electrons with ( equal / different ) forces.
6.
The pull of an atom on the shared electrons that form a bond between it and another atom is called the atom’s
( A ) electronegativity EN ( B ) electron affinity ( C ) valency
7.
If the difference in electronegativity ΔEN < 1 between the two non-metal atoms that are bonded together, we call
this a ( very weakly polar covalent / a polar covalent ) bond
8.
If ΔEN < 1, then the two different non-metal atoms that are bonded, form a molecule that is ( polar / non-polar ).
9.
A non-polar molecule has positive and negative charges on its surface that are ( noticeable / trivially small ).
10.
If ΔEN > 1 then the two different non-metal atoms that are bonded form a molecule that is ( polar / non-polar ).
11.
Which diagram represents
11.1 a polar molecule 11.2 a non-polar molecule (A) + (B)

12.
The electronegativity of C is 2,5. The electronegativity of H is 2,1.
The difference in electronegativity of the C ‒ H bond is ........ so a hydrocarbon has ( polar / non-polar ) bonds.
13. heptane pentane
The bonds between non-polar hydrocarbon molecules are
( London dispersion forces / dipole-dipole forces / hydrogen bonds ).
14.
14.1 Longer hydrocarbon chains tend to form ( stronger / weaker )
London dispersion forces.
14.2 Longer hydrocarbon chains have ( higher / lower ) boiling points.
15.
butane propane ethane methane
C4H10 C 3H 8 C 2H 6 CH4

15.1 Which alkane gas has the biggest molecule with the greatest molar mass?
15.2 Which alkane gas has the most electrons in each of its molecules?
15.3 Which alkane gas has the biggest contact area between neighbouring molecules?
15.4 Which alkane gas has the strongest London dispersion forces between its molecules?
15.5 Which alkane gas has the highest boiling point?
15.6 In 2010 satellites measured ‒93 ºC in Antarctica near Russian base Vostok. What is the only cooking gas
that can be used there on such a cold day? ( This is the coldest measured temperature on Earth ).
16.
What is another name for weak van der Waals forces?
Boiling point 78 ºC
17.
17.1 Name the two kinds of intermolecular forces found in 1-chlorobutane. C4H9Cℓ
17.2 Why has butane got a much lower boiling point of 0 ºC.
C4H10
17.3 Fluorine, F, is too dangerous to work with. Excluding F, which element has the highest electronegativity?
17.4 Excluding F, which element forms the strongest dipoles when bonded to other non-metal elements?
17.5 Name 3 homologous series that have an O atom bonded to a C atom with a double bond to make a dipole.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 Page 54 of 107
 Organic Molecules - Structure and Physical properties ACTIVITIES 2
18. ( Memo Page 62 - 63 )
18.1 The strongest bonds between molecules are ( dipole-dipole forces / hydrogen bonds ).
18.2.1 To form a hydrogen bond within the limits of the matric syllabus, an O atom must bond with a ...........atom
that is part of the OH group.
18.2.2 Hydrogen bonds are only accepted on an O atom if they are formed by a H atom in an ........... group.
18.3 For matric :
18.3.1 Hydrogen bonds only form in a homologous series if the molecules contain the .................group.
18.3.2 Which two homologous series have an OH group?
18.3.3 Which two homologous series can form hydrogen bonds? O H‒O

19. CH3‒ C dimer C ‒ CH3

19.1 Why can ethanoic acid form a dimer ?
O‒H O
19.2 State two reasons why ethanoic acid has a higher boiling point ( 118 ºC ) than ethanol ( 78 ºC ).
20.
20.1 Molecules with a bigger molar mass have a ( higher / lower ) boiling point.
20.2 To compare the boiling points of different functional groups, what physical quantity must stay constant?
20.3 What does Mr = 72 u mean?
20.4 Given the following information :
CH3CH2CH2CH2CH3 pentane Mr = 72 Boiling point = 36 °C
CH3CH2CH2CHO butanal Mr = 72 Boiling point = 76 °C
CH3CH2CH2CH2OH butan-1-ol Mr = 74 Boiling point = 118 °C
Write down the names of the intermolecular forces between the molecules of each type of substance.
Choose from : London dispersion forces, dipole - dipole forces, hydrogen bonds.
21.
The polarity of molecules determines the forces of attraction between the molecules in the liquid state.
Each pole of a polar molecule is attracted by an oppositely charged pole. (the positive end of one molecule is
attracted to the negative end of another molecule).
Molecules have different degrees of polarity as determined by the type of ................. group present.
22.
Increasing polarity of the functional group causes an increasing strength of intermolecular forces which leads to an
increasing boiling point
The order of decreasing boiling points is A > B > Ketone ~ Aldehyde > C > D
Identify the letters from the following functional groups : alkane, alcohol, carboxylic acid, ester
23.
Why is the carbonyl group polar?
What bonds form between carbonyl groups?

24.
Why do haloalkanes have higher boiling points than alkane molecules that have a similar mass?

chloroethane Mr = 64,5 Cℓ
butane Mr = 58
boiling point 0 ºC boiling point 12 ºC
+

Cℓ

25.
Why do aldehydes and ketones have lower boiling points than an alcohol of similar molecular mass?

26.
26.1 Which intermolecular forces considerably raise the boiling point of haloalkanes above that of alkanes?
26.2 Which forces predominate between the non-polar alkyl chains of polar haloalkane molecules?

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 Page 55 of 107
 Organic Molecules - Structure and Physical properties ACTIVITIES 2
27. ( Memo Page 63 - 64 )
What intermolecular forces exist between ester molecules of ethyl ethanoate? O
II
CH3 C ‒ O ‒ C CH3
28.
For the homologous alkane series, why is the boiling point of pentane 36 ºC while the boiling point of propane is
only ‒42 ºC.

propane pentane

29.
What is the relationship between between the boiling point of isomers and their degree of branching?

30.
You are given three isomers : pentane, methylbutane and dimethylpropane.
You are given three boiling points : 30 ºC , 10 ºC and 36 ºC.
Match each isomer with its correct boiling point.

31.
Generally speaking, the melting points of substances usually increases as the boiling points increase.
But spherical molecules ( also called symmetrical molecules ) although they have lower boiling points yet they
have higher melting points . Explain.

32.
32.1 Explain the following order of boiling points :
Hexanal 130 ºC hexan-2-one 126 ºC hexan-3-one 120 ºC

O O
O

32.2 O O
II II
Two ester isomers, CH3CH2 CH2 CH2‒ O ‒ CH and CH3 ‒ O ‒ C CH2 CH2CH3 are tested for their boiling points.
One boiling point is measured as 112 ºC and the other is measured as 107 ºC.
Match each isomer to its boiling point. Explain
butyl methanoate methyl butanoate

O
O
O
O

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 Page 56 of 107
 Organic Molecules - Structure and Physical properties ACTIVITIES 2
33. ( Memo Page 64 )
Why do alkene molecules have lower boiling points compared to alkane molecules of the same chain length?

H H H H
C 2H 6 C 2H 4
H C C H H C= C H
H H
34.
Why do alkyne molecules have higher boiling points compared to alkane molecules of the same chain length?
This reason is a bit tricky.

35.
35.1 How do gas particles exert pressure?
35.2 Define boiling point.
35.3 The liquid with the weakest intermolecular forces evaporates ( most / least ) to produce the
( most / least ) vapour molecules.
36.
Two liquids, A and B, are enclosed in sealed containers at room temperature.

liquid A B
Which liquid, A or B
36.1 is the most volatile? 36.2 evaporates the fastest?
36.3 produces the most vapour? 36.4 has the highest vapour pressure?
36.5 has the weakest intermolecular forces? 36.6 has the highest boiling point?

37.
Choose the right answer.
BP means boiling point. VP means vapour pressure.

strong intermolecular forces weak intermolecular forces

A high BP, high VP low BP, low VP
B high BP, low VP low BP, high VP
C low BP, low VP high BP, low VP
D low BP, high VP high BP, high VP

38.

The following vapour pressures, measured by the ability of the vapour pressure to support a thin column of
mercury in a thin tube, were recorded for pentane and two of its isomers.
The height of the mercury ( Hg ) column, measured in millimetres ( mm ) indicates the vapour pressure.
The temperature was kept constant at 21 ºC because hotter gases move faster and collide harder with the sides of
the container, increasing their vapour pressure.

dimethylpropane Vapour pressure = 1 100 mm Hg ( at 21 °C)

methylbutane Vapour pressure = 595 mm Hg ( at 21 °C)
pentane Vapour pressure = 441 mm Hg ( at 21 °C)

What is the relationship between the boiling point of an isomer and its degree of branching?

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 Page 57 of 107
 Organic Chemistry - Structure and Physical Properties
Past Matric Papers
( Memo Page 65 )
1
1.1 The haloalkanes known as CFC’s are no longer used in fire extinguishers and aerosol cans because they
are expensive to manufacture. Is this statement true or false.

1.2 Which ONE of the following compounds will have the highest boiling point?

A CH3CH2CH2CH2CH3 B CH3CH2CH2CH2 O CH3 ( ether )

C CH3CH2CH2CH2 CH2OH D CH3CH2CH2 C CH3

II
O
1.3 Which of the following are structural isomers of hexane?
(i) CH3 ― CH2 ― CH ― CH2 ‒ CH3 ( ii ) CH3 ―CH2 CH3

CH2CH3 CH2 ―CH2 ― CH2

( iii ) CH3 ―CH― CH2―CH3

CH2 ―CH3

A (i) and (ii) only B (ii) and (iii) only C (i), (ii) and (iii) D (i) and (iii) only

2.
Hydrocarbons are simple organic compounds. The homologous series called alkanes is one group of hydrocarbons.
One physical property of alkanes is shown in the table below.

NAME BOILING POINT (°C) ISOMER BOILING POINT OF ISOMER (°C)

methane ‒ 161,0
ethane ‒ 88,5
butane ‒1 methylpropane ‒ 12
pentane 34 2-methylbutane 28
hexane 68,7 2,3-dimethylbutane 58

2.1 Define the concept homologous series. (2)

2.2 Explain the change in boiling points of the alkanes from methane to hexane. (2)

2.3 How do the boiling points of the straight chain compounds differ from that of their corresponding isomers.
Give a reason for this difference. (3)

2.4 Write down the structural formula of the isomer of hexane shown in the table. (2)

2.5 The human body secretes oils that maintain the moisture of the skin. Alkanes, such as non-polar petrol
and paint thinners, dissolve non-polar organic material such as fats and oils.

Explain why people must minimise contact with hydrocarbon solvents such as paint thinner. (2)

2.6
Petroleum jelly (Vaseline) is a soft semi-solid mixture of hydrocarbons that provides a protective film when
used on the skin. It is hydrophobic (water repelling) and is, for example, used on burns or to prevent
nappy rash on babies.
2.6.1 Which physical property of Vaseline explains why it does not flow like petrol? (1)
2.6.2 Boiling water is accidentally spilled on a child. Explain why Vaseline should not be used on the
child’s skin immediately after sustaining burns. (2)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers Page 58 of 107
 Organic Molecules - Structure and Physical properties Past Matric Papers
3. ( Memo Page 65 - 66 )
The first six members of the alkanes occur as gases and liquids at normal temperatures. Alkanes are currently our
most important fuels, but the use of alcohols as renewable energy sources is becoming more and more important.
Alcohols are liquids that might be a solution to the energy crisis.
3.1 Which chemical property of alkanes and alcohols make them suitable to be used as fuels? (2)
3.2 The table below shows the boiling points of the first six alkanes and the first six alcohols.

Alkane Boiling point (°C) Alcohol Boiling point (°C)

methane ‒ 164 methanol 65
ethane ‒ 89 ethanol 79
propane ‒ 42 1-propanol 97
butane ‒ 0,5 1-butanol 117
pentane 36 1-pentanol 138
hexane 69 1-hexanol 156

Draw a graph of boiling points versus number of carbon atoms for the first six ALCOHOLS.
Choose 50°C and 1 carbon atom as origin and use an appropriate scale.
Plot the points and draw the best curve through the points on the graph paper below. (5)

3.3 What trend can be observed from the graph? (2)

3.4 Explain the trend mentioned in Question 3.3 by referring to the type of intermolecular forces. (2)
3.5 Explain, referring to the type of intermolecular forces, why the boiling points of alcohols are higher than the
boiling points of alkanes. (2)
3.6 People are always cautioned to keep liquids such as petrol (a mixture of alkanes) out of reach of children.
Refer to the physical properties of alkanes and justify this precaution. (2)
3.7 Briefly explain why ethanol is a renewable energy source, while the alkanes are non-renewable. (2)

3.2 Graph of boiling points versus number of carbon atoms

170

150

130
Boiling points ( ºC )

110

90

70

50
1 2 3 4 5 6 Number of carbon atoms

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers Page 59 of 107
 Organic Molecules - Structure and Physical properties Past Matric Papers
4. ( Memo Page 66 )
4.1 The boiling points of branched alkanes are lower than those of straight chain alkanes containing the same
number of carbon atoms because branched alkane chains have …

A larger molecular masses.

B shorter chain lengths.
C more electrons.
D smaller effective molecular surface areas.

4.2
There are two structural isomers for the organic compound with molecular formula C2H4O2.

4.2.1 Define the term structural isomer. (2)

4.2.2 Write down the structural formula of these two isomers and next to each its IUPAC name. (3 x 2) (6)

4.2.3 State with reason which ONE of these isomers:

4.2.3.1 Has the higher boiling point (3)

4.2.3.2 Has the higher vapour pressure (3)

4.2.4 Will the vapour pressure of carboxylic acids increase or decrease if the number of carbon atoms in the
chain increases? Write down a reason for your answer. (3)
5.
The environmental effects of CFCs and their substitutes
The ozone layer protects the earth and its inhabitants from the dangerous ultraviolet rays of the sun. It was
discovered that gases such as chlorofluorocarbons (CFCs) had damaged the ozone layer, creating a huge hole
through which dangerous ultraviolet light could reach the earth.
CFCs were widely used as cooling agents in air conditioners and refrigerators and as propellants in aerosol cans
because of their special physical properties. CFCs can be produced by the reaction of alkanes with chlorine,
followed by the reaction of the resulting product with fluorine.

Since the banning of CFCs in the year 2000, hydrocarbons such as propane and
2-methylpropane are now used as more environmentally friendly alternatives to CFCs.
Both these hydrocarbons and CFCs are greenhouse gases.
However, CFCs have a greater global warming potential.
5.1 The structural formula for a commonly used CFC is given below.
F
I
Cℓ – C – F
I
Cℓ
Write down the IUPAC name for this CFC. (2)

5.2 Which physical property of CFCs makes them suitable for use as cooling agents and propellant gases?(1)
5.3 CFCs have a negative impact on the environment.
5.3.1 State this negative impact. (1)
5.3.2 Describe how this negative impact also affects human health. (2)

5.4 Use condensed structural formulae to write a balanced equation for the preparation of chloroethane from
ethane.
(3)
5.5 State ONE reaction condition needed for the reaction in QUESTION 5.4 to occur. (1)
5.6 Write down a structural formula of an isomer of 2-methylpropane. (2)
5.7 Give TWO reasons why propane and 2-methylpropane are considered more environmentally friendly than
CFCs.
(2)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers Page 60 of 107
 Organic Molecules - Structure and Physical properties Past Matric Papers
6. ( Memo Page 66 - 67 )
The table below shows data collected for four organic compounds, represented by the letters A — D,
during a practical investigation.

Organic Compound Relative Molecular Mass Boiling Point ( ºC )

A 44 ‒ 42
CH3CH2CH3
B CH3CHO 44 21

C CH3CH2COH 46 78

6.1 Is compound A a saturated or an unsaturated hydrocarbon? Write down a reason for your answer. (2)
6.2 To which homologous series does compound B belong? (1)
6.3 Write down the IUPAC name for each of the following compounds:
6.3.1 A (1) 6.3.2 B (1) 6.3.3 C (1)
6.4 Which variable was controlled during this investigation? (1)
6.5 Name the following in this investigation:
6.5.1 The dependent variable (1)
6.5.2 The independent variable (1)
6.6 Refer to intermolecular forces to explain the difference in boiling points between compounds A and C. (3)
6.7 Which ONE of compound B or C will have the highest vapour pressure at a specific temperature?
Write down a reason for your answer. (2)
7.1 Consider the structural formula and IUPAC name of each compound shown below.
H H H H H H H
I I I I I I I
H ‒C‒C‒C‒H H ‒C‒C‒O‒H H ‒C‒C‒F
I I I I I I I
H H H H H H H
propane ethanol fluoroethane
Which ONE of these compounds has the highest vapour pressure at room temperature?

A Propane B None of them C Ethanol D Fluoroethane

7.2 The table below shows the results obtained during a practical investigation.
Two experiments were performed to determine the boiling points of compounds from three different
homologous series under the same conditions.
Each letter A to F represents the organic compound written in the block next to it.
Experiment Organic compound Molar mass (g•mol‒1) Boiling point (°C)

A CH3COOH 60,5 118

B CH3CH2CH2OH 60,1 97
I
C CH3CH2CHO 58,1 48

D CH3(CH2)2COOH 88,1 163

E CH3(CH2)3CH2OH 88,1 137

II
F CH3(CH2)3CHO 88,1 103

7.2.1 Name the homologous series to which each of the following pairs of compounds belong:

7.2.1.1 A and D (1) 7.2.1.2 B and E (1) 7.2.1.3 C and F (1)

7.2.2 Write down the IUPAC name for: 7.2.2.1 Compound C (1) 7.2.2.2 Compound E (1)

7.3 Refer to intermolecular forces to explain the trend in boiling points, as shown
7.3.1 in the table I. (3) 7.3.2 in the table II compared to table I. (3)
F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers Page 61 of 107
Organic Chemistry - Structure and Physical Properties Activities 2 MEMORANDUM
( Questions from Page 54 - 55 )
1. covalent bonds 2. van der Waals forces 3. stronger 4. atoms
5. different 6. A 7. very weakly polar covalent bond 8. non-polar
9. trivially small 10. polar 11.1 A 11.2 B 12. ΔEN = 2,5 ‒ 2,1 = 0,4 non-polar
13. London dispersion forces 14.1 stronger 14.2 higher
15.
15.1 butane 15.2 butane 15.3 butane 15.4 butane 15.5 butane
15.6 methane. All the rest are liquids at ‒93 ºC.
16. London dispersion forces
17.
17.1 Dipole - dipole forces, London dispersion forces
17.2 The chlorine atom has a stronger electronegativity of 3 so it sets up a more polar molecule which can form
dipole-dipole forces. The large mass of the chlorine atom and its many electrons enable it to form stronger London
dispersion forces. Thus the boiling point rises as it takes more thermal energy to break these stronger attractive
forces. 17.3 Oxygen, O 17.4 Oxygen, O
17.5 esters O ketone O aldehyde O
II II II
‒C‒O‒C‒ ‒C ‒C‒C‒ ‒C‒H
18.
18.1 hydrogen bonds 18.2.1 H atom 18.2.2 OH 18.3.1 OH
18.3.2 carboxylic acids, alcohols 18.3.3 carboxylic acids, alcohols

19.1 Each O atom can form a hydrogen bond with the H atom in the OH group. Two such hydrogen bonds form
between two acid molecules, creating a dimer.

O
O
O O
dimer
O
carboxylic acid O alcohol

19.2 Alcohols have one site, the OH group, for forming hydrogen bonds.
In addition, van der Waals forces (dipole-dipole forces and London dispersion forces ) exist between molecules.
Carboxylic acids have two sites, the O and the OH, for forming hydrogen bonds. Carboxylic acids can form a
dimer which doubles the molecular mass and this increased molecular size increases the strength of the
dipole - dipole forces and the London dispersion forces between the neighbouring dimers.
20.
20.1 higher 20.2 the molar mass of each molecule 20.3 the relative molar mass = 72 atomic mass units
( protons and neutrons ) on a scale where carbon-12 has been allocated a mass of 12 atomic mass units.
20.4 Pentane has London dispersion forces only between molecules.
Butanal has dipole-dipole forces ( caused by the C = O carbonyl group ) as well as London dispersion forces.
Butan-1-ol has London dispersion forces, dipole - dipole forces ( caused by the O atoms ) and hydrogen bonds
caused by the OH group.
21. functional group
22.
Carboxylic acid A > Alcohol B > Ketone ~ Aldehyde > Ester C > Alkane D

23.
The carbonyl group ( C = O ) is polar since oxygen is more electronegative than carbon and forms a partially
charged dipole. Thus dipole-dipole forces exist between carbonyl groups.
In addition there are London dispersion forces between carbonyl groups.
dipole-dipole forces dipole-dipole forces
δ‒ δ+ δ‒ δ+
carbonyl ‒C‒
O O
group II
O carbonyl II
O
group ‒C‒
δ+ δ‒ δ+ δ‒
London dispersion forces
London dispersion forces

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 MEMORANDUM Page 62 of 107
 Organic Molecules - Structure and Physical properties ACTIVITIES 2 Memorandum
24. butane Mr = 58 ( Questions from Page 55 - 56 )

boiling point 0 ºC chloroethane Mr = 64,5 Cℓ

London dispersion forces boiling point 12 ºC

+ dipole-dipole forces
London dispersion forces
Cℓ

+
Alkanes only have weak London dispersion forces between molecules.
For haloalkanes, the chlorine atom is more electronegative than the carbon atom which creates partial negative
and positive charges that form a dipole. Thus dipole-dipole forces are set up between neighbouring molecules
which are stronger than London dispersion forces. In addition the haloalkanes also have London dispersion forces
between molecules..
25.
Since ketones and aldehydes lack hydroxyl groups, they are incapable of forming intermolecular hydrogen
bonds and are less polar than alcohols.
26.
26.1 Boiling points of haloalkanes are considerable higher than that of alkanes due to weak intermolecular
dipole-dipole forces.
26.2 London dispersion forces exist between the non-polar parts of the haloalkane molecules.
27.
Dipole-dipole forces and London dispersion forces.
28.
propane pentane

Boiling points depend on surface area and chain length.

For compounds with the same functional group, the longer the carbon chain, the larger the surface area and the
higher the boiling point. A larger surface area has more sites where London dispersion forces can form.
The combined effect of all the London dispersion forces results in stronger intermolecular forces, and thus a higher
boiling point.
Increasing chain length, increasing surface area, increasing strength of intermolecular forces, increasing boiling
point
29.

Boiling points of isomers decrease with branching

because the contact area between neighbouring
molecules decreases as the molecules get more spherical.
30.
Boiling points of isomers decrease with branching.
dimethylpropane boiling point = 10 °C methylbutane boiling point = 30 °C pentane BP = 36 ºC
31.
Symmetrical molecules can pack more closely in a crystal network, resulting in a higher melting point, i.e. the
temperature at which the solid changes to the liquid phase, for such a compound. Liquid molecules are not
packed into crystal networks and therefore symmetry will not affect boiling points i.e. the
temperature where a liquid changes to a gas.
Closely packed spherical molecules in a solid form strong bonds due to the closeness of each
molecule to its neighbours. Bonds get stronger as molecules get closer.
It takes a lot of energy to break these attractive intermolecular forces.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 MEMORANDUM Page 63 of 107
 Organic Molecules - Structure and Physical properties ACTIVITIES 2 Memorandum
32. ( Questions from Page 56 - 57 )
32.1 δ‒
O δ‒ δ‒
O O
δ+
δ+
δ+
Hexanal 130 ºC hexan-2-one 126 ºC hexan-3-one 120 ºC

The molecules are all isomers with the same molar mass, thus their London dispersion forces are equally strong.
The strongest inter molecular forces produced by these polar molecules are the dipole-dipole forces caused by the
partial negative charge on the oxygen atoms. The closer each O atom gets to the centre of the chain, the more the
two sections of the alkyl chains can fold around the O atom and shield it from contact with other polar molecules,
which weakens the dipole-dipole forces, lowering the boiling point.
32.2 δ‒ 107 ºC.
112 ºC
O δ‒
O O
δ+ O
butyl methanoate methyl butanoate
δ+
In butyl methanoate the substituent partially negatively charged oxygen atom at the end of the chain cannot be
effectively shielded from the dipole-dipole forces of other molecules. Thus its boiling point will be higher.
In methyl butanoate the substituent O atom is more effectively shielded because it is in the middle of the chain
and the two portions of the chain can fold around it to shield it from other polar molecules which weakens these
dipole-dipole forces and lowers the boiling point.

33.
alkane Non-polar molecules – weak London dispersion forces.
alkene Non-polar molecules – weak London dispersion forces.
For the same number of C atoms, boiling points are slightly lower than that of alkanes.
London dispersion forces depend on the shape of the molecule and the number of electrons it contains.
Each alkene has two electrons less than the alkane with the same number of C atoms.
34.
Alkynes are non-polar molecules with weak London dispersion forces.
Alkyne molecules are more polarisable ( i.e. electron clouds are deformed easier to form temporary dipoles ) due
to the four pi-electrons forming the second and third bond that are loosely held. Therefore alkynes have
higher boiling points than alkanes ( and alkenes ) with the same number of C atoms in their chains.
35.
35.1 Gas particles exert pressure by colliding with the sides of the bubble.
35.2 Boiling point is the temperature at which the vapour pressure of a substance equals atmospheric
pressure.
35.3 most, most
36.
36.1 B. Volatile means evaporate to produce the most vapour.
36.2 B 36.3 B
36.4 B Vapour pressure is due to fast moving vapour particles colliding with the sides of the container.
So the liquid that produces the most vapour will have most collisions and thus the highest vapour pressure.
36.5 B Weaker intermolecular forces between the liquid molecules are are easier to break and thus allow the
molecules to escape from the liquid and form a gas or vapour.
36.6 A The liquid with least vapour has the strongest intermolecular forces. But the vapour pressure must
increase to equal atmospheric pressure before boiling occurs. To achieve this, more vapour particles must be
produced and thus the liquid must be heated more strongly to break sufficient liquid bonds.
37.
B Stronger intermolecular forces produce a higher boiling point but a lower vapour pressure.
Weaker intermolecular forces produce a lower boiling point but a higher vapour pressure.
38.
Boiling points of isomers decrease with branching. As the chains become more branched, they
become more spherical and have less surface area in contact which weakens the intermolecular forces. They
evaporate faster and reach boiling point at a lower temperature. High vapour pressure means a low boiling point.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Activities 2 MEMORANDUM Page 64 of 107
 Organic Chemistry - Structure and Physical Properties Past Matric Papers
Memorandum
( Questions from Page 58 - 59 )
1.1 False … because they are harmful to the environment. and because they deplete the ozone layer.
1.2 C. Only - OH ( and ̶ COOH ) form hydrogen bonds. O-atoms form weaker dipole-dipole bonds.
1.3 B Each has six C atoms
2.1 A group of organic compounds that can be represented by the same general formula
2.2 Molecular mass / size of molecules increase therefore London dispersion forces increase.
2.3 Straight chain alkanes have higher boiling points than that of corresponding branched chains
Branched chains become more compact, so the surface contact decreases.
Therefore intermolecular forces are weaker, hence lower boiling point.
2.4 H
I
H‒C‒H

H H H 2.5 The thinners will dissolve the fats and oils in the skin, and leave the
I I I skin dry and damaged.
H‒C‒C‒C‒C ‒H 2.6.1 Viscosity
I I I 2.6.2 The Vaseline will form a layer on the skin that traps thermal energy
H H H and increases the pain from the burns.
H‒C‒H
I
3. H
3.1 High energy of combustion which means that their combustion releases huge amounts of energy and their
combustion is highly exothermic

3.2 Graph of boiling points versus number of carbon atoms

170

150

Criteria for graph:

130
Correct heading 
Boiling points ( ºC )

Correct scale on both axes 

Both axes labelled correctly 
Points correctly plotted 
Best curve drawn through points
110


90

70

50
Number of carbon atoms
1 2 3 4 5 6

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers MEMORANDUM Page 65 of 107
 Organic Molecules - Structure and Physical properties Past Matric Papers Memorandum
3.3 Boiling point increases with number of carbon atoms ( Questions from Page 59 - 61 )
3.4 London dispersion forces between alcohol molecules increase with increase in molecular size
3.5 Hydrogen bonds between alcohol molecules are stronger than London dispersion forces between
molecules of alkanes
3.6 Petrol has a low boiling point and vapourises easily, thus is volatile, mixture is explosive and flammable,
easily combustible.
Vapours have a higher density than oxygen and when swallowed or inhaled vapours can cause suffocation.
3.7 Ethanol can be produced by fermentation of plant material e.g. maize and sugar cane.
Alkanes are fossil fuels which are non-renewable.
4.1 D
4.2
4.2.1 Structural isomers are organic molecules with the same molecular formula but different structural formulae.
4.2.2 O H methylmethanoate H O ethanoic acid
II I I II
H‒C‒O‒C‒H H‒C‒C‒O‒H
I I
H H
4.2.3.1 Ethanoic acid
• The hydrogen bonds are the intermolecular forces between ethanoic acid molecules and they are stronger
than the dipole-dipole forces and London dispersion forces which are the intermolecular forces between
methyl methanoate molecules.
• More energy needed to break bonds between ethanoic acid molecules.
4.2.3.2 Methyl methanoate.The London dispersion forces and dipole-dipole forces are the
intermolecular forces between the ester molecules.
These are weaker than the hydrogen bonds which are the intermolecular forces between ethanoic
acid molecules.
• Less energy is needed to break the bonds between the ester molecules.
4.2.4 Decrease.
London dispersion forces increase with molecular size.
5.
5.1 Dichlorodifluoromethane
5.2 Low boiling point OR High volatility/high vapour pressure
5.3.1 Damages the ozone layer
5.3.2 Increase in (dangerous) UV rays that reaches earth
Higher occurrence of skin cancer and cataracts on the eyes.
5.4 CH3CH3 + Cℓ2 → CH3CH2Cℓ + HCℓ
5.5 Heat / thermal energy or ultraviolet or sunlight
5.6 H H H H
I I I I
H–C–C–C–C–H
I I I I
H H H H
5.7 F makes the molecules stable so it lasts a long time in the upper atmosphere. Cℓ attacks the high altitude
ozone.
Propane has no C or F so it causes no harm to the ozone layer.
It is a less potent greenhouse gas – contributes less to global warming or climate change.
6.
6.1 Saturated. Contains only carbon-carbon single bonds OR No carbon-carbon double or triple bonds
OR Each carbon bonded to four other atoms
6.2 Aldehydes
6.3.1 Propane 6.3.2 Ethanal 6.3.3 propan-1-ol 6.4 Relative molecular mass / molecular size
6.5.1 Boiling point
6.5.2 Type of organic compound / type of homologous series / type of functional group
6.6 Between the alkane molecules of compound A (propane) are weak London dispersion intermolecular forces
• Between the alcohol molecules of compound C (propan-1-ol) are weak London dispersion forces as well as
dipole-dipole forces and strong hydrogen bonds
• More energy is needed to overcome the stronger intermolecular forces between alcohol molecules of
compound C (propan-1-ol)
OR Less energy is needed to overcome intermolecular forces between the alkane molecules of compound A ,
the propane molecules
6.7 Compound B. Lower boiling point due to weaker intermolecular forces.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers MEMORANDUM Page 66 of 107
 Organic Molecules - Structure and Physical properties Past Matric Papers Memorandum
7.1 A propane only has weak London dispersion forces. ( Questions from Page 61 )
The other two form stronger hydrogen bonds which limit the amount that they evaporate to form vapour particles.
7.2.1.1 Carboxylic acids 7.2.1.2 Alcohols 7.2.1.3 Aldehydes
7.2.2.1 Propanal 7.2.2.2 Pentan-1-ol
∂‒
7.3.1 H
O ∂+
‒O‒H The O atom in OH has two lone pairs that can form hydrogen
∂‒ bonds with H atoms in other OH functional groups.
Boiling point of carboxylic acids > alcohols > aldehydes.
There is a relationship between boiling point and type of functional group or homologous series.
Carboxylic acids – highest boiling points due to strongest hydrogen bonding as more hydrogen bonds form between
the two oxygen atoms and the hydrogen atom in the OH hydroxyl group.
hydrogen bond
The dashed lines represent
O H‒O
hydrogen bonds between the O atoms
and the H atoms in an OH hydroxyl CH3‒ C dimer C ‒ CH3
functional group.
Two acid molecules can form a dimer O‒H O London dispersion forces
with their hydrogen bonding.
This doubles the mass of the molecule O H‒O
giving it stronger London dispersion
forces to bond with neighbouring dimers. CH3‒ C dimer C ‒ CH3
O O‒H
Alcohols – lower boiling points than carboxylic acids due to weaker hydrogen bonding as fewer hydrogen bonds
form from a single oxygen atom and a single hydrogen atom in the OH hydroxyl group. Also, the carboxyl group
( COOH ) of a carboxylic acid is more polar than the hydroxyl group ( OH ) of an alcohol and this forms stronger
hydrogen bonds than the OH group. But alcohols have higher boiling points than aldehydes due to these stronger
hydrogen bonds between alcohol molecules compared to aldehydes that have much weaker London dispersion
forces and the weaker dipole-dipole forces that each oxygen atom forms between molecules.
H ‒ O ‒ C CH2 CH3

CH3 CH2 C ‒ O ‒ H

CH3 CH2 C ‒ O ‒ H
Aldehydes – lowest boiling points due to only the dipole-dipole forces and London dispersion forces forming
weaker intermolecular forces between molecules. The oxygen atom cannot form a hydrogen bond as there is no
OH hydroxyl functional group to provide a hydrogen atom to form the hydrogen bond.

O
II
CH3 CH2 C ‒ H
dipole-dipole and London dispersion forces
O
II
CH3 CH2 C ‒ H
7.3.2
Relationship between boiling point and chain length or molar mass of compounds with the same functional group
from the same homologous series.
Compounds in Experiment 2 have higher boiling points than compounds in Experiment 1.
Chain length of compounds in Experiment 2 are longer than in Experiment 1.
London dispersion forces , caused by distortions of the electron clouds, form the intermolecular forces between
longer C chains and these forces increase with increase in chain length due to the increase in molecular size as
more C atoms are added and the increasing number of electrons which increases the number of contact points
between the distorted electron clouds.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Structure and Physical Properties Matric Past Papers MEMORANDUM Page 67 of 107
 TOPIC : Organic Molecules - Chemical Reactions NOTES
Bur ning hydrocarbons ( in excess oxygen ) is very exothermic ∆H < 0
• products are always CO2 and H2O
• first balance C, then H, then O by inspection ( juggling the numbers till they are equal on both sides )
EXAMPLE 1
Balance C5 H12 ( ℓ ) + O2 (g) CO2 (g) + H2O (g)
This reaction happens at a high temperature so water will form as gaseous steam.
First balance C : C5 H12 + O2 5 CO2 + H2O Combustion reaction
Then balance H : C5 H12 + O2 5 CO2 + 6 H2O
Then balance O : C5 H12 ( ℓ ) + 8 O2 (g) 5 CO2 (g) + 6 H2O (g) ΔH < 0.

Alkanes are our most important fuels.

The combustion of alkanes is highly exothermic
and carbon dioxide and water are produced

Petrol is one of the main fuel

sources for transportation.
It burns with hardly any soot.

EXAMPLE 2
Balance C5 H10 ( ℓ ) + O2 (g) CO2 (g) + H2O (g)
First balance C : C5 H10 + O2 5 CO2 + H2O
Then balance H : C5 H10 + O2 5 CO2 + 5 H2O
Then balance O : C5 H10 + 7,5 O2 5 CO2 + 5 H2O
or
Double everything 2 C5 H10 ( ℓ ) + 15 O2 (g) 10 CO2 (g) + 10 H2O (g) ΔH < 0.

www.indexmundi.com/energy.aspx
The world uses about 12 000 tons of oil every day ( one barrel is about 120 kg of oil ).
About half of this is turned into petrol.
Modern petrol is a very complex mixture of about 200 components and additives.
The main use of alkanes is as fuels.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 68 of 107
 Organic Molecules - Chemical Reactions NOTES
Esterification is an acid catalysed condensation between an alcohol and a carboxylic acid.
The double bond is on the acid side of the molecule.
alcohol donates H acid donates OH ( to form water )
H H O H H2SO4 H H O H H H
H H O
H C C O + O C C H → H C C O C C H +

H H H H H H ester

ethanol + ethanoic acid → ethyl ethanoate

+ water
Boiling point 77ºC
O

O O
O
O

H2SO4 extracts H and OH. This is an elimination reaction. Condensation as H‒OH forms
Concentrated H2SO4 is a strong dehydrating agent.
O water
Heat reactants for 15 minutes in a water bath at about 75 ºC.

The equilibrium constant is not too far from being 1, thus the reaction does not really proceed by itself.
We need to drive the equilibrium to favour the forward reaction (using Le Chatelier’s Principle) in order to make
the ester.
This is done by removing the water chemically using excess sulfuric acid as a dehydrating agent.
The forward reaction is then favoured to replace the missing water.

This is a condensation reaction, in which two molecules link up by the elimination of a small molecule
between them; in this case, water.
warning sign
When the alcohol was made from radioactive oxygen-18 then no traces of
radioactivity were found in the water that formed as a product. Thus the oxygen
in the water does not come from the alcohol. It must thus come from the acid.
The concentrated sulfuric acid extracts an H and an OH to form water.

AROMAS :
methyl ethanoate Glue or nail polish remover. Methyl ethanoate is a solvent for glue.
methyl salicylate Wintergreen (smell of iodine)
ethyl ethanoate fruity, glue or nail polish remover
3-methylbutyl ethanoate Banana smell
pentyl salicylate Floral smell
pentyl ethanoate Pear smell O
O
Functional group for esters : II
– C – O – C ‒ ester group alcohol R – O – C – R ’ acid

hexyl propanoate H H H H H H H H R and R’ represent alkyl groups

H C C C C C C O C C C H Eg. methyl. ethyl, propyl, butyl,
pentyl, hexyl, heptyl, octyl
H H H H H H O H H

Esters has many uses, such as artificial fruit essences and aroma enhancers, artificial flavours for confectionery,
ice cream and cakes, as a solvent in many applications (including decaffeinating tea and coffee) for varnishes and
paints (nail varnish remover), and for the manufacture of printing inks and perfumes.

cakes ice cream printer’s ink solvent perfume paint solvents

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 69 of 107
 Organic Molecules - Chemical Reactions NOTES
We classify reactions according to the structural change that occurs
1. Addition reactions
If a double bond between two C-atoms snaps, we can add two monovalent atoms to this molecule.
Addition reactions are reactions where atoms are added to a molecule by the breaking of a double bond.
between the carbon atoms without the removal of any atoms from the molecule.
Thus unsaturated compounds undergo addition reactions to form saturated compounds.
H H H H
• one of the double bond snaps to make 2 single bonds C C C C
• unsaturated compounds become saturated H H H H
• other atoms can add onto these single bonds

( a ) Hydrogenation is the addition of hydrogen to an alkene

( The adding of H atoms to saturate a compound ). Dissolve gas in liquid to increase concentration of C2H2.
Heating increases the reaction rate but as the solvent gets hotter, the alkene gets less soluble in it. So it must not
get too hot, say about 150 ºC. ( Compare with fizzy drinks that dissolve more CO2 when cold and taste better )
H H Ni / Pt H H
C C C2H4 + H2 C2H6
+ H–H H C C H
H H heat H H ethane
ethene dissolved in non-polar solvent.
The ethyne and H2 molecules can break old bonds and be adsorbed as they bond onto the finely divided
or powdered Ni surface. ( Platinum, Pt, or palladium, Pd, can be used as catalysts ).
“Adsorb” means the atoms are only attached to the surface of the metal. They are not absorbed into the metal.
The small H atoms then have time to move on the Ni surface to join up with the stationary ethyne molecule.
Palladium, we do not know why, can attach itself to a huge amount of hydrogen gas.
If H atoms are absorbed into a metal, then the reaction is usually almost irreversible as it forms metal
hydrides.
A non-polar solvent is advised because polar ones may inhibit the catalyst by preferential adsorption on the
surface. The polar charge can induce an opposite charge on the metal and thus stick more easily onto the metal.

+ old bonds snap

Ni catalyst surface

Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni Ni catalyst
surface

new bonds form

The new molecule is desorbed as it breaks

Ni Ni Ni Ni Ni Ni away from the catalyst. So a catalyst must hold
Ni Ni
atoms fairly strongly but not too strongly.
Metals like platinum and nickel make good catalysts. They adsorb atoms strongly enough to hold them close
to each other for long enough to activate the reactants and get them to bond.
But not strongly enough that the new products can’t break away.
Analogy. Often a boy marries the girl next door because they have known each other long enough to develop
a relationship. Today many people endlessly move around to do their work and often never see anyone for long
enough to develop a relationship that can lead to marriage.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 70 of 107
 Organic Molecules - Chemical Reactions NOTES
Making margarine H2 gas

• bubble hydrogen gas through sunflower oil

• the temperature is 300°C
• the catalyst used is nickel nickel sieve
H2 gas
H2
Hydrogenation produces saturated hydrocarbons sunflower oil
with larger molar masses causing stronger van der
Waals forces which produce higher melting points.
hydrogen cylinder
heat
Thus they tend to be solids rather than liquids. 300°C

As the double bonds snap the margarine becomes saturated with H-atoms, and gets harder.

Polyunsaturated margarine has more double bonds and is softer.

(b) Halogenation is the reaction of a halogen ( Br2 , Cℓ2 ) with a compound

H H H H
C C + Br – Br Br C C Br C2 H4 + Br2 C2 H4 Br2
H H H H 1,2-dibromoethane
Colourless liquid

+
Br Br
Br Br

Any of the diatomic halogens can be represented but Br is mainly used. Cℓ reacts in the same way, but faster.
( But iodine I reacts too slowly and fluorine F is explosive ).
The reaction happens readily without heat or sunlight or a catalyst at room temperature.
If you have a gaseous alkene like ethene, you can bubble it through either pure liquid bromine or a solution of
non-polar bromine in an inert non-polar organic solvent like dichloromethane CH2Cℓ2.
The reddish-brown bromine is decolourised as it reacts with the ethene.
C2H2 gas
Non-polar substances dissolve in
non-polar liquids or solvents.

reddish-brown

bromine dissolved in dichloromethane

ethene cylinder

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page71 of 107
 Organic Molecules - Chemical Reactions NOTES

(c) Hydration is the addition of water to a compound

Hydration is the splitting the water molecule ( H2O → H + OH ) and adding the two parts across a double
bond to form a single product, an alcohol.
300°C H H H H
H H H2SO4 H
60 atmospheres C C + O H C C O
H H ∆ H H
H2O in excess steam ethanol
ethene
A small amount of H3PO4 or some strong acid acts as a catalyst to catalyse the addition of water.
Ethene is mixed with steam and passed over a catalyst consisting of solid silicon dioxide ( sand ) coated with
phosphoric acid or some strong acid.
The temperature used is 300°C to ensure the water remains as gaseous steam. High temperature increases the
reaction rate. The pressure is about 60 atmospheres ( 6 MPa.).
High pressure is needed to compress the gases together to make them react.
old bonds snap

O O
+
+

O
new bonds form

The sulfuric acid is a catalyst that takes part in the reaction and then is recovered unchanged at the end.
Water is not a strong enough acid to react with the electron-rich double bond, but with excess water and a
small amount of added H2SO4 (or H3PO4), the H2O forms H3O+ that readily reacts with the double bond.
Hydration is thus acid-catalysed.

(d) Hydrohalogenation is the addition of a hydrogen halide to to an alkene

H H H Br H 2-bromopropane
H C C C + H – Br H C C C H
H H H H H H
unreactive solvent About 70% of this major product forms
( adding Aℓ2O3 speeds up the rate )
Reaction conditions :
HBr is added to the alkene. The acid HBr ( or HCℓ ) must be water-free as a dried gas that has no
water vapour mixed with it. Dissolve the HBr in a non-polar solvent CH2Cℓ2.
No water must be present or else an OH will add on instead of the Br. Acids catalyse the addition
of water. Br only has an electronegativity of 2,8 compared to O with EN = 3,5.
Thus the O in OH is more reactive than Br and competes with the Br to take part in the addition..
Markovnikov's rule
• the H atom looks for the most "friends" and attaches to the C atom that already has the greater number of
H-atoms
( in this case it will be the end carbon )
• the halogen atom attaches to the C atom that has the more substituted atoms i.e. the least number of H-atoms

H H Br

H C C C H 1-bromopropane Only a much smaller amount of this minor product usually forms.

H H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 72 of 107
 Organic Molecules - Chemical Reactions NOTES
2. Elimination reactions
This reaction turns single bonds between carbon atoms into double bonds.
Saturated compounds undergo elimination reactions to form unsaturated compounds.
(a) dehydration of alcohols is the elimination of water from an alcohol

Heating of ethanol with an excess of concentrated sulfuric acid or phosphoric acid as a catalyst.
Concentrated sulfuric acid ( or phosphoric acid ) is a dehydrating agent that absorbs water by removing an H+
and an OH ‒ from a molecule and then combining them to make water.
Acid catalysed dehydration of ethanol by heating the alcohol to 170 ºC with an excess of concentrated H2SO4
( or H3PO4 ). The acid dehydrates the alcohol and the high temperature ensures that it is a gas phase reaction.
H H H H H H
conc H2SO4
H C C O–H C C + O dehydration reaction
∆
H H heat H H
170 ºC
old bonds snap

O O

O
+
( Hot concentrated solutions produce elimination )
new bonds form
C2 H5 OH → C2 H2 + H2O
We can get the same result by passing ethanol vapour over a heated catalyst such as Aℓ2O3 powder.
Aℓ2O3
CH3CH2OH (g) → CH2 = CH2 (g) + H2O (g)

This is a gas phase elimination reaction as the liquids are all gases at a hot enough temperature.
Zaitsev’s rule
H H H H H H H H H H
conc H2SO4 + O
H C C C C H H C C =C C H
∆
H H O H H H
H
If more than one elimination product is possible, the major product is the one where the H-atom is removed
from the C-atom with the least number of H-atoms. ( Zaitsev’s rule ).
Not from an end carbon that has 3 H-atoms.

H H H H H H H H H H
conc H2SO4 + O
H C C C C H H C C ‒C=C H
∆
H H O H H H
H
A far smaller amount of the minor product forms, removing the H-atom from the carbon atom with the most
number of H-atoms. This is the end carbon with three H-atoms.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 73 of 107
 Organic Molecules - Chemical Reactions NOTES
( b ) Dehydrohalogenation is the elimination of hydrogen and a halogen from a haloalkane
Elimination of HX from a haloalkane ( X is any halogen ).
CH2Cℓ ‒ CH2Cℓ (g) → CH2 = CHCℓ (g) + HCℓ (g)
Δ H H H H
∆
H C C H C C + HCℓ
heat
Gas phase elimination reaction used in industry. H Cℓ
Cℓ Cℓ
1,2-dichloroethane chloroethene

• Cℓ 2 is too energetic as a halogen in column 7 and thus it cannot form in these elimination reactions
which do not have sufficient energy to make a high energy product.
Elimination reactions can also be done at high temperatures when reactants and products are gases.
Haloalkanes tend to be liquids and must be heated to turn them into gases and then further heated to drive the gas
phase elimination reaction.
• Gas phase elimination reactions are well known in industry.
• But bromo compounds are avoided in industry because bromine is expensive.

Reaction conditions for a laboratory experiment :

Dissolve the haloalkane in a hot concentrated solution of NaOH or KOH in a pure ethanol solvent
Heat under reflux. The vapours enter a thin vertical reflux tube.
They cool down and condense back into a liquid which flows back into the reaction vessel.

This reaction needs a strong base. Group I or Group II metal hydroxides. reflux tube
The NaOH does not fully ionise in the ethanol so there are fewer OH‒ ions as any
excess OH‒ ions will substitute with the Br ‒ making an unwanted hydrolysis product.
cool air
Br

+ NaOH vapour liquid

( ionic )

+ Na Br
O
+
( ionic )
water bath
A solvent of pure ethanol is to maximize the solubility of the haloalkane.
Such compounds are generally poorly soluble in water and their solubility will be greatest in hot plate
ethanol when there is no water.
Zaitsev's rule : if more than one elimination product is possible the major product is the one where
the double bond will appear between the carbon atoms where the H is removed from the carbon that
already has the least number of H-atoms. ( eg. C number 3 from the left has 2 H )
Using a strong base as a reactant causes elimination at a lower temperature.

H Br H H concentrated strong base H H H H

+ O
H C C C C H + Na OH H C C C C H + Na Br
heat under
H H H H reflux H H H H
2-bromobutane This is the major product that forms ( but-2-ene ).
Normally three products form.
Hot ethanolic NaOH solvent
Hot, concentrated solutions cause elimination reactions. Also use pure ethanol.
Warm, dilute solutions cause substitution reactions that use more water in the solvent mixture.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 74 of 107
 Organic Molecules - Chemical Reactions NOTES
( c ) Cracking Crude Oil hydrocarbons in a Fractionating Column
A mixture of gases bubbles though the liquid in a tray that is kept at a certain temperature. Gases of that liquid will
condense in the tray, the other gases rise to condense at a lower temperature in the higher trays.

gases 120°C gases LPG C1 - C4

coolest
liquid petroleum gas
paraffin
170°C gases oil naptha for chemicals
70°C Cracking is the
C5 - C7
chemical process
A fractionating column has a series of trays,
in which longer
each at a constant temperature, thus many 120°C petrol C5 - C10 chain hydrocarbon
separate distillations are able to occur.
molecules are
Consequently, a liquid mixture can be
broken down to
separated into its different components. paraffin and jet fuel
170°C shorter more useful
Fractional distillation of crude oil. C10 - C16 molecules.
Crude oil is a mixture of many different
components. 270°C diesel fuels C14 - C20
Crude oil evaporates when heated to 700ºC.
The different vapours of its components are able
to condense at different temperatures in the
fractionating column. wax C20 - C50
Each fraction consists of hydrocarbon molecules
containing a similar number of carbon atoms. fuel oil for ships and
600°C
factories
crude oil from C20 - C70
fur nace ( feedstock ) 700°C
bitumen for tar roads
hottest > C70

Cracking Naphtha Alkane Chains ( done at SASOL )

Heavy naptha has 7 - 12 carbon atoms in a chain ( boiling points range from 75ºC to 200ºC )
These can be split up or cracked to yield petrol ( gasoline ) and petrochemicals.

Light naptha has 5 - 6 carbon atoms in a chain ( boiling points range from 20ºC to 75ºC ) yield ethene
Cracking of hydrocarbons
• thermal cracking : high pressures and temperatures without a catalyst.
Unbranched products form with low octane rating. Side branches can’t form under high pressure.
• catalytic cracking : lower temperatures and pressures, about 500ºC, in the presence of a catalyst form more
highly branched alkanes from which petrol is made with a higher octane rating.
Fortunately, mixtures of alkanes with similar boiling points are perfectly suitable for use as fuels, solvents and
lubricants.
Pyrolysis chemically decomposes organic materials by heating in the absence of oxygen.
( the breaking up of a molecule when heated )
Consider pentane which can split up into four different chain lengths. Each with an unpaired electron..making a
highly reactive free radical.

or
CH3CH2CH2CH2CH3 → CH3 • + • CH2CH2CH2CH3
free radicals
CH3CH2CH2CH2CH3 → CH CH • + • CH CH CH 3 2 2 2 3
These free radicals may recombine to form a mixture of different alkanes
If the unpaired electrons on each free radical join up with each other to form a bonding pair of electrons.
CH3 • + • CH3 → CH3CH3 ethane

CH3CH2 • + • CH3 → CH3CH2CH3 propane

Cracking forms a shorter chain.

CH3CH2 • + • CH2CH2CH2CH3 → CH3CH2CH2CH2CH2CH3 hexane

Cracking forms a longer chain.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 75 of 107
 Organic Molecules - Chemical Reactions NOTES
Or
the free radicals can perform another reaction ( called disproportionation )
This is another possible reaction during the thermal cracking and produces alkenes.
To make ethene, an ethyl free radical is needed because it has two C atoms.
A hydrogen atom ( with its electron ) is transferred from the C atom that is next to the C with the
unpaired free radical electron. This H transfer to another free radical produces an alkane and an alkene.
H H H H H H H H H
H C + H C C → H C H + H C C → H C H + C C
H H H H H H H H
transfer H
The two unpaired methane ethene
This reaction requires a high electrons form a
C 2H 4
temperature to enable the fast second ( pi ) bond
moving H atom to break its bond
and a high pressure to force the
gasses together so that they react.
Thermal cracking, no catalyst.
CH3 • + CH3CH2 • → CH4 + CH2 = CH2

Catalytic cracking of C10H22 into three possible products, two alkenes and ONE alkane
( always one alkane amongst the many alkenes )
The unpaired electrons form a double bond
C10 H22 (ℓ ) → C2H4 (g) + C5 H12 (ℓ) + C3H6 (g) (Assume C10 H22 breaks up into these 3 segments)
H H H H HH H H H H H H H H HH H H H H
I I I I I I I I I I I I I I I I I I I I
H–C ‒C C– C–C‒C‒C C–C‒C‒H → H–C ‒C + H C– C–C‒C‒C H + C–C‒C‒H
I I I I I I I I I I I I I I I I
H H H H H H H H HH H H H H H H H H

Abstraction : H H H H HH H H H H
both the H and its electron move I I I I I I I I I I
to join an unpaired electron. → H–C = C‒H + H‒C– C–C‒C‒C‒H + H‒C=C‒C‒H
The H comes from the C atom I I I I I I
next to the unpaired electron. H H H H H H
ethene pentane propene
Elimination or cracking of alkanes

Dehydrogenation reaction is the elimination of hydrogen from an alkane.

Saturated ethane is cracked to unsaturated ethene and H2 (g) Heat strongly and gas molecules move
faster.
H H H H Use high pressure to confine this
Pt movement of the molecules.
H C C H C C + H–H
∆ 800ºC Thus the energy goes into vibrating the
H H H H hydrogen atoms so that they can be
shaken off the ethane molecule.

This is a gas phase elimination reaction driven by high temperature.

Single bonds are strong.
At a very high temperature the C atoms vibrate so strongly that each C atom can shake off a H atom.

CH3CH3 (g) → CH2 = CH2 (g) + H2 (g)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 76 of 107
 Organic Molecules - Chemical Reactions NOTES
SASOL's gas - to - liquid ( GTL ) process
Natural gas ( methane CH4 ) from Mozambique is reformed into synthesis gas using steam and O2 at high
temperatures ( it is an endothermic reaction ).
CH4 + H2O → CO + 3 H2 ( synthesis gas or syngas ) ∆H > 0

The C from CO and the H from H2 can be joined together to make many hydrocarbon chains.
Sasol uses the Fischer-Tropsch technology to convert synthesis gas ( derived from natural gas or coal ) into
petrol and other fuels.
The hydrogen and carbon monoxide react under pressure at a moderate temperature.
An iron-based catalyst in fluid form is added.
This produces a broad spectrum of hydrocarbons, usually in the C1 - C20 range.
The C2 rich stream ( those hydrocarbons with two C atoms ) is split into ethene and ethane.
The ethane is cracked in a high-temperature furnace, producing ethene. The ethene is then purified.

The longer-chain olefins ( alkenes ) ( C8 - C11 ) are introduced into the fuel pool to make petrol.
The double bonds break and enable side chains to form which have better anti-knock properties in petrol.
CH3 CH3
100 % octane is CH3 ‒ C ‒ CH2 ‒ CH
CH3 CH3

The more compact molecule of 2,2,4-trimethylpentane compresses less and produces less knocking under
pressure.
Longer fuel molecules compress too much inside the car engine and self-explode at the wrong time ( which is
called knocking ) since compression causes heating.
3. Substitution reactions

( only HCℓ and HBr, Br2 and Cℓ2 )

Substitution reactions are reactions in which one atom or group of atoms is replaced by another

These occur VERY SLOWLY in saturated compounds.

(a) Halogenation of alkanes is the reaction of a halogen ( Br2, Cℓ2 ) with a compound

ethane + bromine gas in the presence of light or heat

• one Br atom swaps places with an H atom to form bromoethane
• liquid Br 2 does not readily attack single bonds in an alkane

light energy
H H H H
hf
H C C H + Br – Br (g) H C C Br + H–Br
∆
H H H H
heating

Br Br Br
+

swap Br

C2 H6 + Br2 C2 H5 Br + HBr

Alkane to haloalkane.
The brown colour of the bromine disappears slowly in the presence of heat or sunlight.

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 Organic Molecules - Chemical Reactions NOTES
(b) Reactions of haloalkanes with bases ( hydrolysis ) to produce alcohols
The non-polar haloalkane is dissolved in ethanol so that it can mix with dilute aqueous NaOH and then the
mixture is warmed to increase the reaction rate.
• ethanol can dissolve polar and non-polar substances
• the non-metal Br is substituted by the non-metal OH group

H H H dilute strong base H H H Normally only 2 products.

H
H C C C Br + Na OH H C C C O + Na Br
∆
H H H H H H
mild heat

( If the base is too concentrated, elimination of H and Br to form propene + NaBr and H ‒ OH occurs ).
swap

O
Br +
Na

O + Br

Na

The same hydrolysis reaction occurs more slowly without the alkali NaOH.
Water is added to a haloalkane dissolved in ethanol. and mildly heated. ( Water behaves as if it is H ‒ OH )
CH3 ( CH2 )2 Br + HOH → CH3 ( CH2 )2 OH + HBr
The advantage of this slower reaction, using water is that no elimination occurs.
This is because water releases far fewer OH groups than what NaOH will do. Too many OH will cause elimination.
A concentrated strong base will cause elimination as an unwanted by product of the substitution reaction.
swap

O
Br +

O +
Br

( c ) Hydrolysis is the reaction of a compound with water

The hydrolysis reaction, without the alkali, takes place very slowly as the concentration of OH– ions is lower.
excess water Split bromomethane into two parts.
H H H H H Split water into H+ and OH‒
H + O Then exchange functional groups to
C Br H C O + H – Br
∆ form two separate molecules,
H mild heat H an acid and an alcohol.
A hydrolysis reaction is when a compound splits into two parts when reacting with water which also splits into
H+ and OH ‒. The functional groups are exchanged to form two products.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 78 of 107
 Organic Molecules - Chemical Reactions NOTES
Substitution reactions using alcohols and water-free HCℓ or HBr ( dehydrated hydrohalides ).

The OH in water can also replace the OH that is removed from the alcohol molecule as OH is more active than Br.
This process simply reforms the alcohol. This is a waste of time so water must not be included.
• Mild heating increases the reaction rate.
• Strong heating can cause an unwanted elimination reaction.
H H H H H H
H water free H H
H C C C O + H – Br H C C Br + O
C
H mild heat
H H H H H
alcohol + dehydrated hydrohalide haloalkane + water

In the presence of dehydrated acids, alcohols act as bases to form water.

swap

O + Br

O
Br +

Alkenes decolourise yellow-brown bromine water rapidly.

To make bromine water : add a few drops of JIK ( not colour fast bleach.) to some dilute HCℓ to make chlorine
water. The yellow-green colour of Cℓ2 in suspension can be seen.
Pour a little of this chlorine water into a KBr solution in a test tube.
The yellow brown ( amber ) colour of bromine water is visible as the Br2 somehow remains in suspension..
From the E-Standard Table of reduction potentials :

Br2 + 2 e‒  2 Br ‒ + 1,09 V less positive about the forward reaction. ∴ favours reverse reaction.

Cℓ2 + 2 e‒ → 2 Cℓ ‒ + 1,36 V more positive about the forward reaction.

Cℓ2 water

2 Br ‒ → Br2 + 2 e‒ Swop the reverse reaction around.

Cℓ2 + 2 e‒ → 2 Cℓ ‒
bromine Br2
Cℓ2 (aq) + 2 Br ‒ (aq) → 2 Cℓ ‒ (aq) + Br2 (aq) Jik chlorine water
water Br ‒
HCℓ
Arrows must point to the right as products form on the right. Cℓ2 K+ KBr

Add a little of this Br2 water to colourless unsaturated cyclohexene.

Shake the mixture. The colour disappears quickly.
If you use saturated cyclohexane you would have to leave the mixture over night to get Br2 water
rid of the colour as there are no double bonds to quickly snap.
Light and heat can speed up this reaction.
cyclohexene
The concentration of the HCℓ affects the colour of the bromine water which can
range from yellow-brown to red if the HCℓ is fairly concentrated. ( unsaturated )

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Page 79 of 107
 Organic Chemistry - Chemical Reactions Activities 3
1. ( Memo Page 90 - 91 )
Write down balanced equations for the combustion in excess dioxygen of

1.1 C3 H8 + O2 1.2 C3 H6 + O2
1.3 hex-2-ene + dioxygen

2.1 O H
Complete and balance this esterification equation : H H
H C O + O C H

2.2 H
Write a balanced equation for making
2.2.1 methyl propanoate 2.2.2 propyl methanoate.

3.
Complete and balance the following
3.1 3.2
H H H H
C C + H–H C C + Cℓ – Cℓ
H H H H

3.3 H
H
C C + H – Br
H H

4.
4.1 Define hydrogenation 4.2 Define halogenation
4.3 Define hydration 4.4 Define hydrohalogenation
5.
5.1 Complete and balance
H H
| | H H
H–C=C–H + O

5.2 This is called .................. through addition.

5.3 Which reactant must be in excess ?
5.4 What catalysts must be used ?

6.
6.1 Complete and balance
H H H
| | |
H – C = C – C – H + H – Cℓ
|
H
6.2 This reaction is called ....................through addition. 6.3 Water ( must / must not ) be present
6.4 What happens if water is present ? 6.5 State Markovnikov's rule.
7.
7.1 Complete and balance this reaction
H H
| | H Aℓ2O3
H–C –C–O
| | ∆
H H
7.2 This is an ................... reaction.
7.3 What is the role of the Aℓ2O3 powder ?
7.4 What is the state of the ethanol ?

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 Page 80 of 107
 Organic Molecules - Chemical Reactions ACTIVITIES 3
8. ( Memo Page 91 - 92 )
8.1 Complete and balance this
reaction
H H
| | H
H2SO4
H–C –C–O
| |
H H ∆
8.2 This reaction is called ................ through elimination.
8.3 What catalyst is used?
8.4 What two functions does the sulfuric acid perform?

9. State Zaitsev’s rule

10.
10.1 What are two possible elimination products for this reaction ?
H Br H H
| | | |
H – C – C – C – C – H + Na OH
| | | |
H H H H
10.2 Which of the two products is most likely to be the major product ?
10.3 Name the rule that applies to elimination reactions that have more than one possible product.
10.4 What are the elimination reaction conditions for dehydrohalogenation?

11.
11.1 How can pentane crack to form propane?
11.2 What other product can form from the two free radicals that formed propane?

12.
Catalytic cracking of C7H16 can form three possible products as shown

C10 H22 (ℓ ) → 2 C2H4 (g) + X.

What is the structural formula and name for X?

13.
Write down a balanced equation to show how saturated ethane is cracked to unsaturated ethene and H2 (g).
State two reaction conditions
14.
Complete and balance the following

14.1 H H

H C C H + Br – Br
H H

14.2 H H
H C C H + H – Br
H H

14.3 H H
H C C Br + KOH
H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 Page 81 of 107
 Organic Molecules - Chemical Reactions ACTIVITIES 3
15. ( Memo Page 92 )
15.1 What are three reaction conditions for a hydrolysis substitution reaction to occur that uses NaOH and a
non-polar haloalkane.

15.2 Complete and balance the following equation

H excess water
H H
H C Br + O
∆
H mild heat

15.3 Define hydrolysis.

15.4 Mention
one disadvantage and
one advantage
of performing a hydrolysis reaction with water rather than using dilute NaOH.

16.
16.1 Write down formulae for two hydrohalides.
16.2 What is meant by a dehydrated hydrohalide?
16.3 Why must water not be present in the following reaction?

H H H
H water free
H C C C O + H – Cℓ
H mild heat
H H
alcohol + dehydrated hydrohalide haloalkane + water

16.4 Mild heating increases the reaction rate. What happens if the reactants are strongly heated?

16.5 Complete and balance the above equation.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 Page 82 of 107
 Organic Chemistry - Chemical Reactions Past Matric Papers
( Memo Page 93 - 94 )
1.1 What one word describes the elimination of H2O from an alcohol?
1.2 What name describes alkanes in which a hydrogen atom has been substituted by a halogen atom?
1.3 Name a group of compounds that can undergo addition reactions.

2.1 Write down the structural formulae and IUPAC names for the product(s) formed when the following
compounds react

2.1.1 hex-2-ene and HCℓ

2.1.2 CH3 ‒ CH2 ‒ C = CH ‒ CH3 and HBr

I
CH3

2.2 The following equations represent chemical reactions:

Reaction 1: A + HBr → CH3 ‒ CH2 ‒ CH2Br + H2O

NaOH
Reaction 2: CH3 ‒ CH2 ‒ CH2 Br A + NaBr

2.2.1 Name the type of reaction in reaction 2.

2.2.2 Write down the structural formula for the organic compound A.

2.3 Propanol can be oxidised to form compound Y. The functional group of compound Y is …

A —C—C=C— B — OH C — C Ξ C — D — C — OH
II
O

3.
3. 1 Liquid oils are converted to fats such as margarine during a chemical process where hydrogen gas is
bubbled through sunflower oil at 300ºC using a nickel catalyst.
NAME the type of reaction that occurs during this process (1)
3. 2 A gaseous hydrocarbon with 3 carbon atoms per molecule is decolourised by bromine water.
3.2.1 Is this hydrocarbon saturated or unsaturated? (1)
3.2.2 Write down the IUPAC name of the hydrocarbon. (2)
3.2.3 Use structural formulae to write down the equation for the reaction of the hydrocarbon with
bromine.
Hint : Addition reactions involving alkynes are not in the syllabus. (3)
3.3 Write down a structural formula for butan-2-ol and structural formulae for two of its isomers.
(6)
3.4 Study the flow diagram below and answer the questions that follow.
sugars

Process A
Chemical C
Ethanol + methanoic acid B + water

3.4.1 Write down the name of process A through which ethanol is produced.
(2)
3.4.2 Write down the structural formula and IUPAC name for compound B. (4)
3.4.3 What is the name and function of chemical C in the reaction? (2)
4.
4.1 Name the process caused by the addition of hydrogen to an alkyne.
4.2 Describe a test that can be used to distinguish the compound 4-methyl-2-hexyne from the compound
4-methylhexane.

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 Organic Molecules - Past Matric Exams Chemical Reactions
5. ( Memo Page 94 - 95 )
Some organic reactions are shown in the flow diagram below.
X

A Br2
UV light

C3H7 OH B C3H7Br C C3H7OH

propan-1-ol 1-bromopropane propan-1-ol

D concentrated KOH(aq)
heat
Y
5.1 Name the type of reactions illustrated by A, B, C and D. (4)

5.2 Use condensed structural formulae and write a balanced equation for reaction C. (3)

5.3 Write down the structural formula for compound X. (2)

5.4 In order to obtain product Y, C3H7Br is heated with a concentrated solution of KOH under reflux.
Use condensed structural formulae to write a balanced equation for the reaction. (3)

5.5 A group of learners decided to heat C3H7Br with dilute sodium hydroxide, instead of the concentrated
KOH, under reflux. Write down the IUPAC name of the organic compound that they will obtain. (2)

6.1
A simple reaction scheme is shown below
HBr(g) reflux with
CH3CH = CH2 X Y + NaBr
NaOH (aq)
The formula for Y is …

A CH3CH2COOH B CH3CHOHCH3

C CH3CHBrCH2OH D CH3CHOHCH2Br

6.2 Alcohols are prepared by the hydration of alkenes.

Use structural formulae to write down the equation which represents the formation of ethanol. (3)

6.3 Write a balanced chemical equation for the preparation of compound CH3 ‒ Cℓ using an alkane as one of
the reactants. (3)

7.
Ethene is a gaseous hormone associated with the ripening of fruit. It also contributes to the ageing and distortion
of plants. In industry, the artificial ripening of fruit takes place when ethene is passed over the fruit in large rooms.
After a while the ripening fruit releases its own ethene.

7.1 Write down the structural formula of ethene. (2)

7.2 Why is it not advisable to place a banana that has been artificially ripened alongside a cabbage and lettuce?
(2)

In industry ethene is also used to synthesise a variety of organic compounds.

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 Organic Molecules - Past Matric Exams Chemical Reactions
7. ( continued ) In industry ethene is also used to synthesise a variety of ( Memo Page 95 - 96 )
organic compounds. The flow diagram below illustrates some
of the many reactions ethene undergoes.
ethane
A

B
E D
bromoethane ethene ethanol
F C

H
7.3 Write down the general formula for the homologous series to which ethene belongs. (1)

7.4 Name the type of reaction represented by each of the letters A, B, D and H.
Write down the letters A, B, D and H and next to each the type of reaction. (4)

7.5 Use structural formulae to write down a balanced equation for reaction B. (3)

7.6 Apart from ethene, which other reactant is needed for reaction F? Write down the FORMULA only. (2)

7.7 Both reactions E and G occur in the presence of a base.

Reaction E is an elimination reaction and reaction G is a substitution reaction.

7.7.1 How is the base in reaction E different from the base in reaction G? (2)

7.7.2 Name the type of elimination reaction represented by E. (1)

8.
Most organic compounds can undergo substitution or addition or elimination reactions to produce a variety of
organic compounds. Some incomplete organic reactions are represented below.

Reaction I CH3 ‒ CH2 ‒ CH = CH2 + H2O →

Reaction II CH3 ‒ CH2 ‒ CH2 ‒ C = CH2 + HBr →

I
CH3

H2SO4
Reaction III CH3 ‒ CH ‒ CH2 ‒ CH3
I heat
OH

8.1 Name the type of reaction represented by reaction III. (1)

8.2 Both reactions I and II are examples of addition reactions.
Name the type of addition that is represented by each reaction. (2)
8.3 Write down the structural formula and IUPAC name of the major product formed in reaction I. (3)
8.4 Reaction I only takes place in the presence of a catalyst. Write down the formula of the catalyst used in
reaction I.
(1)
8.5 Write down the structural formula and IUPAC name of the major product formed in reaction II. (3)

8.6 To which homologous series does the organic product formed in reaction III belong? (2)

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 Organic Molecules - Past Matric Exams Chemical Reactions
9.1 Use condensed structural formulae to write a balanced equation for the ( Memo Page 96 - 97 )
preparation of chloroethane from ethane. (3)
9.2 State ONE reaction condition needed for the reaction in QUESTION 9.1 to occur. (1)

10.
10.1 In the flow diagram, which shows the conversion of an alcohol into haloalkanes :
10.1 Name the type of organic reaction of which dehydration is an example. (1)

10.2 To which homologous series do compounds P and Q belong? (1)

Compound X + Compound Y

HBr
Compound P
dehydration
butan-2-ol

Compound Q
HBr

Compound X

10.3 What type of reaction takes place when compound P is converted to compounds X and Y as illustrated
above? (1)
10.4 Use structural formulae to write a balanced equation for the preparation of compound Q, which is the major
product, as illustrated above.
(4)
10.5 What identifies Q, as the major product? Give a reason for your answer.
(2)
10.6 Write down the structural formula and the IUPAC name for compound X. (3)

10.7 A learner indicates that he can convert butan-2-ol directly into compound X.
Name the type of reaction that will take place during a direct conversion. (1)

11.
11.1 The chlorination of methane is an addition reaction. Correct this statement.

11.2 Esters are considered derivatives of carboxylic acids and can be prepared by using carboxylic acids as one
of the reactants.
Esters are known for their pleasant smells.
An ester with six carbon atoms is prepared using propanoic acid as one of the reactants.

11.2.1 Use structural formulae to write a balanced equation for the preparation of this ester. (6)

11.2.2 Write down the IUPAC name of this ester. (1)

11.2.3 Write down the name of the catalyst needed for this preparation. (1)

11.3 The flow diagram below shows the conversion of propene to a secondary alcohol.

HBr Substitution
Propene Compound X Secondary alcohol
H 2O
11.3.1 Give a reason why propene is classified as an unsaturated organic compound. (1)
11.3.2 Use structural formulae to write a balanced equation for the formation of compound X. (4)
11.3.3 Name the type of reaction that takes place when propene is converted to compound X. (1)
11.3.4 Write down the structural formula and IUPAC name for the secondary alcohol that is formed. (3)

11.3.5 Name the type of substitution reaction that takes place when compound X is converted to the secondary
alcohol. (1)

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 Organic Molecules - Past Matric Exams Chemical Reactions
11.3.6 With the aid of a catalyst, propene can be converted directly to the ( Memo Page 97 - 98 )
secondary alcohol, without the formation of the intermediate compound X.
11.3.6.1 Besides propene, write down the NAME of the reactant needed for this direct conversion. (1)
11.3.6.2 Write down the FORMULA of a catalyst that can be used. (1)

11.3.6.3 Name the type of reaction that will take place during this direct conversion. (1)

11.3.7 Instead of adding water to compound X, concentrated sodium hydroxide is added and the
mixture is heated.
11.3.7.1 Write down the IUPAC name of the organic product that is formed. (1)

11.3.7.2 Name the type of reaction that takes place. (1)

12.
12.1 Name the type of elimination reaction during which a hydrogen halide is removed from a haloalkane
12.2 Consider the flow diagram below:

H2
propene compound

Pt
The IUPAC name for compound X is:
A propyne.
B propan-1-ol
C propane
D propan-2-ol

12.3 During the dehydration of butan-2-ol, represented below, compound Y forms as one of the products.
H H H H
I I I I dehydration
H – C – C – C –C – H Y
I I I I
H H O H

Which ONE of the following is the correct condensed structural formula for compound Y?

A CH2 CH3 B CH CH3

CH3 CH2 CH3 CH

C CH2 OH D CH2

CH3 CH CH3 CH2 ̶ CH2

I
CH3 OH

12.4 Consider the following terms and compounds in organic chemistry.

aldehydes ketones oxidation haloalkanes hydrolysis

ethyne hydrohalogenation but-1-ene water

hydration chlorine butane potassium hydroxide alkynes

12.4.1 The product formed when an alkane reacts with a halogen. (1)
12.4.2 The reaction of 2-bromobutane with water. (1)
12.4.3 The type of organic reaction during which hydrogen chloride reacts with ethene. (1)

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Matric Past Papers Page 87 of 107
 Organic Molecules - Past Matric Exams Chemical Reactions
13. ( Memo Page 98 - 99 )
Petrol is a complex mixture of hydrocarbons such as hexane.
Compounds such as 2,2,4-trimethylpentane are added to petrol to change, its combustion properties.
13.1 Explain the term hydrocarbon. (2)
13.2 Complete the following equation that represents the complete combustion of hexane in a car engine.
C6H14 + O2 → ... + ... (2)

14.
Many of the flavours and odours of fruits are esters.
Ethyl ethanoate is the most common ester found in wines and contributes to the perception of the fruitiness of wine.
A learner wants to prepare ethyl ethanoate in the school laboratory. She follows the instructions below.
• Mix 1 cm3 ethanoic acid and 1 cm3 ethanol thoroughly in a test tube.
• Slowly add 4 drops of concentrated sulphuric acid while swirling the test tube.
• Soak a paper towel in cold water and fasten it around the test tube close to its mouth with an elastic band.
• Place the test tube in a water bath and heat the water with a flame to a temperature of about 60ºC
• Leave the test tube in the hot water bath for about 15 minutes.
• Cool the test tube by placing it in a beaker of cold water.
• Smell the vapour in the test tube after 10 minutes.

Thermometer

Paper towel soaked in cold water

water bath
Ethanol + ethanoic acid + 4 drops of sulfuric acid

14.1 To which homologous series does ethanol belong? (1)

14.2 Use structural formulae to write a balanced equation for the reaction taking place in the test tube. (5)
14.3 What is the function of the sulphuric acid in the above reaction? (1)
14.4 Why does the method use a water bath instead of direct heating over an open flame? (1)
14.5 State ONE function of the wet paper towel at the top of the test tube. (1)
14.6
The learner finds it difficult to detect the smell of the ester due to the presence of sulfuric acid and unreacted
ethanoic acid.
A friend suggests that she add 10 drops of a diluted sodium carbonate solution to the contents of the test tube.
Briefly explain why this suggestion might be a solution to the problem. (2)

14.7 Whilst several esters may be present in wine, the observed aroma is generally that of the smallest ester
present in wine, namely ethyl ethanoate.
State a physical property of ethyl ethanoate which is responsible for this. (2)

15. Which ONE of the following pairs of reactants can be used to prepare the
ester ethyl butanoate in the laboratory?
A Ethanal and butanol
B Ethanoic acid and butanol
C Ethanol and butanoic acid
D Ethanal and butanoic acid

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Matric Past Papers Page 88 of 107
 Organic Molecules - Past Matric Exams Chemical Reactions
16. ( Memo Page 99 )
Prop-1-ene is a flammable alkene.
16.1 Why is prop-1-ene considered to be a dangerous compound? (1)

Through addition reactions, prop-1-ene can be converted to other compounds, such as alkanes and alcohols.
16.2 Which part of the structure of an alkene allows it to undergo addition reactions? (1)
16.3
In one type of addition reaction, prop-1-ene can be converted to an alcohol.
16.3.1 Use structural formulae to write a balanced equation for the formation of the alcohol during this
addition reaction. (4)
16.3.2 Name the type of addition reaction that takes place. (1)
16.3.3 Write down the name or formula of the catalyst used in this reaction. (1)

16.4 Use molecular formulae to write down a balanced chemical equation for the complete combustion of
propane. (3)
Prop-1-ene be produced from an alcohol by an elimination reaction.
16.5 Use structural formulae to write a balanced chemical equation for the formation of prop-1-ene from a
PRIMARY alcohol. (4)
16.6 Name the type of elimination reaction that takes place. (1)

17.1 Which ONE of the following pairs of compounds correctly represents the products formed during the
COMPLETE combustion of octane?

A CO and H2O B CO and H2 C CO2 and H2 D CO2 and H2O

17.2 Which ONE of the following pairs of reactants can be used to prepare the ester ethyl methanoate in the
laboratory?
A Ethane and methanoic aid B Methanol and ethanoic acid

C Ethanol and methanoic acid D Ethene and methanol

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Matric Past Papers Page 89 of 107
 Organic Chemistry - Chemical Reactions Activities 3 Memorandum
( Questions from Page 80 )
1.
1.1 C3 H8 + 5 O2 3 CO2 + 4 H2O 1.2 C3 H6 + 4,5 O2 3 CO2 + 3 H2O
OR 2 C3 H6 + 9 O2 6 CO2 + 6 H2O
1.3 C6 H12 + 9 O2 6 CO2 + 6 H2O

2.1 O H O
H H
H
H C O O C H → H C O C H + H H
+
H O
H
2.2.1
H O H H H O H H
H H
H C O + O C C C H → H C O C C C H + H H
H H H H H O
H

2.2.2 H H H O H H H O
H H
H C C C O → H + H H
+ O C H C C C O C H
H H H H H H O

3.1
3.2
H H H H
C C H H H H
+H–H H C C H
H H C C + Cℓ‒Cℓ Cℓ C C Cℓ
H H H H
H H
3.3
H H H H
C C + H – Br C
H C Br
H H
H H
4.
4.1 Hydrogenation is the addition of hydrogen to an alkene.
4.2 Halogenation is the reaction of a halogen with a compound.
4.3 Hydration is the addition of water to a compound.
4.4 Hydrohalogenation is the addition of a hydrogen halide to to any alkene.

5. H
5.1 H H O H O
| | / \ H2SO4 | |
H –C =C–H + H H H–C–C–H
I I
H H
5.2 hydration 5.3 water 5.4 small amounts of a halogen acid or other strong acids
6.
6.1 HH H H H H
| I I | | |
H – C = C – C – H + H – Cℓ H –C–C–C–H
| I I I
H H Cℓ H
6.2 hydrohalogenation
6.3 must not
6.4 the - OH is added instead of the - Cℓ
6.5 The H atom is added to the C atom which already is bonded to the most H atoms

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 MEMORANDUM Page 90 of 107
 Organic Molecules - Chemical Reactions ACTIVITIES 3 Memorandum
7. ( Questions from Page 80 - 81 )
7.1 H H
| | H Aℓ2O3
H –C–C – O H –C= C–H
| | Δ I I
H H H H

7.2 elimination / dehydration

7.3 acts as a catalyst
7.4 vapour or gas

8.
8.1 H H
| | H H2SO4
H –C–C–O H –C= C–H + H H
| | Δ I I O
H H H H

8.2 dehydration
8.3 concentrated sulfuric or phosphoric acid
8.4 It acts as a dehydrating agent and as a catalyst.
9. If more than one elimination product is possible, the major product is the one where the H-atom is
removed from the C-atom with the least number of H-atoms. ( Zaitsev’s rule ).
Not from an end carbon that has 3 H-atoms.
10. but-2-ene
10.1 H Br H H H H
| | I I | |
H – C – C – C – C – H + NaOH H– C – C = C – C –H + NaBr + H ‒ O ‒ H
| | | I ∆ I I I I
H H H H H H H H

but-1-ene
H Br H H H H
| | I I | |
H – C – C – C – C – H + NaOH H– C = C – C – C –H + NaBr + H ‒ O ‒ H
| | | I ∆ I I I I
H H H H H H H H
10.2 but-2-ene
10.3 Zaitsev. Remove the H from the C that has fewest H atoms
10.4 Dissolve the haloalkane in a hot concentrated solution of NaOH or KOH in an ethanol solvent i.e.
absence of water.
11.
11.1 Step 1 : pentane can split into two fragments in two different ways, to form free radicals.

CH3CH2CH2CH2CH3 → CH3 • + • CH2CH2CH2CH3

or CH3CH2CH2CH2CH3 → CH3CH2 • + • CH2CH2CH3

Step 2 : If the unpaired electrons on each free radical join up with each other to form a bonding pair of electrons.
CH3CH2 • + • CH3 → CH3CH2CH3 ( propane )

11.2 CH3 • + CH3CH2 • → CH4 + CH2 = CH2

methane ethene
Abstraction .
A hydrogen atom ( with its electron ) is transferred. The two unpaired electrons form a double bond.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 MEMORANDUM Page 91 of 107
 Organic Molecules - Chemical Reactions ACTIVITIES 3 Memorandum
12. ( Questions from Page 81 - 82 )
H H H HH H H H H HH H H H
I I I I I I I I I I I I I I
H–C ‒C C‒C‒C C‒C‒H → H–C ‒C + H C‒C‒C H + C‒C‒H
I I I I I I I I I I
H H H H H H H H H H H H

Abstraction : H H H HH H H
both the H and its electron move I I I I I I I
to join an unpaired electron. → H–C = C‒H + H ‒ C–C‒C‒H + H‒C=C‒H
The H comes from the C atom I I I
next to the unpaired electron. H H H
ethene propane ethene

13.
H H H H
Pt
H C C H C C + H–H
∆ 800ºC
H H H H
High temperature. 800 ºC. Use platinum ( Pt ) as a catalyst.
14.
14.1
H H H H
H C C H + Br – Br H C C Br + H – Br
H H H H
14.2
H H
H C C H + H – Br no reaction.
H H
H2 is too explosively energetic to be made from this low energy substitution reaction.
14.3 H H H H
H C C Br + Na–OH H C C OH + Na – Br
H H H H
15.
15.1 The non-polar haloalkane is dissolved in ethanol so that it can mix with dilute aqueous NaOH and then the
mixture is warmed to increase the reaction rate. Hydrolysis.
• ethanol can dissolve polar and non-polar substances
• the non-metal Br is substituted by the non-metal OH group
15.2
excess water
H H H H H
H C Br + O O
H C + H – Br
∆
H mild heat H
15.3 Hydrolysis is the reaction of a compound with water ( The splitting of a chemical bond with water )
15.4 The reaction is very slow but no unwanted elimination byproducts are formed.

16.
16.1 HBr, HCℓ 16.2 water-free 16.3 The OH in water can also replace the OH that is removed from
the alcohol molecule as OH is more active than Br. This process simply reforms the alcohol and is a waste of time.
16.4 Strong heating can cause an unwanted elimination reaction instead of the substitution reaction that we want..
16.5 H H H H H H
H water free H H
H C C C O + H – Cℓ H C C C Cℓ + O

H H H mild heat
H H H

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Activities 3 MEMORANDUM Page 92 of 107
 Organic Chemistry - Chemical Reactions Past Matric Papers
Memorandum
( Questions from Page 83 )
1.1 Elimination
1.2 haloalkanes
1.3 Alkenes, alkynes
2.1.1
H H H H H H H Cℓ H H H H The H is added to the end C
I I I I I I I I I I I I atom of the double bond that had
C = C ‒ C ‒ C ‒ C ‒ C ‒ H + HCℓ → H‒C‒C‒C‒C‒C‒C‒H more H atoms than the second
I I I I I I I I I I I carbon atom that only had one
H H H H H H H H H H H H atom.

2.1.2 H H Br H H
I I I I I
H‒C‒C‒C‒C‒C‒H
I I I I
H H H H 3-bromo-3-methylpentane
H‒C‒H
2.2.1 Substitution I
H
2.2.2 CH3‒CH2‒CH2OH
2.3 D an alcohol is oxidised to an aldehyde and then to a carboxylic acid.
3.
3.1 hydrogenation
3.2.1 unsaturated
3.2.2 propene or propyne
3.2.3 H H H Br Br
I I H I I I
H–C–C=C + Br2 → H–C–C–C–H
I I H I I I
H H H H H

3.3 H
H H O H H H H H
I I I I I I I I H
H–C–C–C–C–H H–C–C–C–C–O
I I I I I I I I
H H H H H H H H

H
H O H H H H
I I I I I I H
H–C–C–C–H H–C–C–C–O
I I I I
H H H H

H–C–H H–C–H
I I
H H
3.4.1 fermentation
3.4.2 H H O
I I II
H – C – C – O – C – H ethyl methanoate
I I
H H
3.4.3 concentrated sulfuric acid acts as a dehydrating agent and thus a catalyst.
4.1 Hydrogenation

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 93 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
( Questions from Page 83 - 85 )

4.2 4-methyl-2-hexyne, being unsaturated, will decolorise bromine water quickly, while 4-methylhexane, being
saturated, will not decolorise bromine water unless placed in sunlight or heated.
5.
5.1 A: Substitution OR halogenation

B: Substitution

C: Substitution

D: elimination OR dehydrohalogenation

5.2 CH3CH2CH2Br + H2O → CH3CH2CH2OH + HBr

OR
CH3CH2CH2Br + OH– → CH3CH2CH2OH + Br –
(react with dilute base in ethanol)
5.3
H H H
I I I
H‒C‒C‒C‒H
I I I
H H H

5.4 CH3CH2CH2Br + KOH → CH2 = CHCH3 + KBr + H2O

5.5 Propan-1-ol OR 1-propanol

CH3CH2CH2Br + KOH → CH3CH2CH2OH + KBr
Warm, dilute base produces a substitution reaction.
Hot, concentrated base produces an elimination reaction.
6.1 addition
CH3CH = CH2 + HBr → CH3CHBrCH3
The H goes to the C atom across the double bond that has more H atoms.
substitution
CH3CHBrCH3 + NaOH → CH3CHOHCH3 + NaBr

6.2 H H
H H H H I I H
C=C + O → H‒C‒C‒O
H H I I
H H

6.3 CH4 + Cℓ2 → CH3Cℓ + HCℓ

7.
7.1 H H
C=C
H H

7.2 The ethene liberated by the banana ages the cabbage and lettuce which will become spoiled or rotten and
will change colour.

7.3 CnH2n

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 94 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
7.4 ( Questions from Page 85 )
A : substitution ( halogenation / bromination )

H H H H
I I I I
H ‒ C ‒ C ‒ H + Br ‒ Br → H ‒ C ‒ C ‒ Br + H ‒ Br
I I I I
H H H H

B : addition ( hydrogenation )
H H
H H I I
C=C + H‒H → H‒C‒C‒H
H H I I
H H
D : addition ( hydration )
H H
H H I I H
C=C + H ‒ OH → H‒C‒C‒O
H H I I
H H
H : substitution
H H H H
I I H I I H H
H‒C‒C‒O + H ‒ Br → H ‒ C ‒ C ‒ Br + O
I I I I
H H H H
7.5 H H
H H I I
C=C + H‒H → H‒C‒C‒H
H H I I
H H
7.6 HB
7.7.1 E: concentrated base solutions cause elimination.
G: dilute base solutions cause substitution reactions
The base is more concentrated in reaction E than in reaction G because the base in reaction E is dissolved in
ethanol and no water has been added.
7.7.2
Dehydrohalogenation as both H and Br are eliminated from the
haloalkane.
H H
I I H H
H ‒ C ‒ C ‒ Br + NaOH → C=C + NaBr + H‒OH
I I H H
H H
8.
8.1 III - elimination / dehydration

The concentrated sulfuric acid removes water.

H OH H H H H
I I I I I I
H ‒ C ‒ C ‒ C ‒ C ‒ H → H ‒ C ‒ C = C ‒ C ‒ H
I I I I I I I I
H H H H H H H H
but-2-ene
8.2 I – hydration
II – hydrohalogenation

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 95 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
8.3 Hydration : water acts as H ‒ OH. ( Questions from Page 85 - 86 )
The H adds across the double bond to the C atom that has more H atoms.
H H H H H H OH H
I I I I I I I I
H ‒ C ‒ C ‒ C = C ‒ H + H ‒ OH → H ‒ C ‒ C ‒ C ‒ C ‒ H
I I I I I I
H H H H H H
butan-2-ol
8.4 H2SO4

8.5 hydrohalogenation : HBr acts as H ‒ Br.

The H adds across the double bond to the C atom that has more H atoms.
H H H H H H H Br H
I I I I I I I I
H ‒ C ‒ C ‒ C ‒ C = C + H ‒ Br → H ‒ C ‒ C ‒ C ‒ C ‒ C ‒ H
I I I I I I I
H H H H H H H H
H ‒ C ‒ H H‒C‒H
I I
H H
2-bromo-2-methylpentane
8.6 Alkenes
9.
9.1 CH3CH3 + Cℓ2 → CH3CH2Cℓ + HCℓ
9.2 Heat / thermal energy or ultraviolet or sunlight

10.
10.1 Elimination
H H H H H H H H ( Questions from Page 85 )
I I I I I I I I
H–C–C–C–C–H → H–C–C=C–C–H + H H
I I I I I I O
H H O H H H

H major product : H removed from C with fewest H atoms

but-2-ene
OR

H H H H H H H H
I I I I I I I I
H–C–C–C–C–H → H–C–C‒C=C–H + H H
I I I I I I O
H H O H H H

H
minor product : H removed from C with most H atoms
but-1-ene
10.2 Alkenes
10.3 Addition / hydrohalogenation / hydrobromination

10.4 H H H H H H H H
I I I I I I I I
H–C–C–C–C–H → H–C–C=C–C–H + H H
I I I I I I O
H H O H H H

10.5 Q. The major product is the one in which the H atom is removed from the least substituted C atom
( the C atom with the least number of hydrogen atoms )

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 96 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
( Questions from Page 86 - 87 )
10.6 H H H H
I I I I
H–C–C–C–C–H 2-bromobutane 10.7 substitution
I I I I
H H Br H
11.1 … substitution reaction
H H
I I
H ‒ C ‒ H + Cℓ 2 → H ‒ C ‒ Cℓ + HCℓ
I I
H H

11.2.1
The structural formula of a compound shows which atoms are attached to which within the molecule. The atoms
are represented by their chemical symbols, and lines are used to represent the bonds that hold the atoms to-
gether.
H H O H H H H H H O H H
I I II H I I I H I I I II I I
H–C–C–C–O + H–C–C–C–O → H–C–C–C–O–C–C–C–H + H H
I I I I I I I I I I O
H H H H H H H H H H

11.2.2 propyl propanoate

11.2.3 concentrated sulfuric acid
11.3
11.3.1 Contains a double bond between two carbon atoms.
OR Carbon is not bonded to the maximum number of H atoms.
11.3.2 H H H H H H
I I I I I I
H – C – C = C – H + H – Br → H – C – C – C – H
I I I I
H H Br H
11.3.3 Addition / hydrohalogenation / hydrobromination
11.3.4 H H H
I I I
H–C–C–C–H propan-2-ol
I I I
H O H

H
H H H H H H
I I I H H I I I
H– C–C –C –H + O → H – C – C – C – H + HBr
I I I I I I
H Br H H O H

H
11.3.5 Hydrolysis
H
I H conc H2SO4 H H H
H H
H‒C‒ C C + O H C C C H
I ∆
H H O H
H
propene H propan-2-ol

11.3.6.1 Water
11.3.6.2 H3PO4 / H2SO4 / HCℓ / HBr
11.3.6.3 Addition / hydration

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 97 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
11.3.7.1 ( Questions from Page 87 - 88 )
H H H H H H
I I I I I I H H
H – C – C – C – H + NaOH → H – C – C = C – H + NaBr + O
I I I Δ I
H Br H H
Hot concentrated NaOH produces an elimination reaction.
11.3.7.1 propene
11.3.7.2 Dehydrohalogenation OR elimination.
12.1 dehydrohalogenation
12.2
H H H H H
\I I I I
C=C – C–H + H–H → H–C– C– C–H
/ I I I I I
H H H H H H
propane ( C )
12.3
H H H H H H H H
I I I I I I I I O
H–C– C–C–C–H → H–C–C = C–C–H + H H
I I I I I I
H H O H H H Zaitsev’s rule : remove H from C that has fewest H atoms
/
H CH CH3 (B)
/ \\ /
CH3 CH
12.4.1 haloalkane
12.4.2 hydrolysis ( bromobutane splits into two parts, butane and bromine. Water splits into H and OH.
The OH adds to the butane to make butan-2-ol and the H adds to the Br to make HBr )
H H H H H H H H
I I I I O I I I I
H – C– C– C–C– H + H H H – C– C– C–C– H + H – Br
I I I I I I I I
H Br H H H O H H
\
H
12.4.3 H H
\ /
H – C ≡ C – H + H – Cℓ → C=C hydrohalogenation
/ \
H Cℓ
13.1 Hydrocarbons are molecules consisting of hydrogen and carbon atoms only
13.2 2 C6 H14 + 19 O2 → 12 CO2 + 14 H2O

14.
14.1 alcohols or alkanols
14.2 . H O H H H O H H
I II H H I I I II I I O
H—C—C—O + O—C—C—H → H—C—C—O—C—C—H + H H
I I I I I I
H H H H H H
14.3 Dehydrating agent and catalyst
14.4 The ester organic molecule is delicate and will be destroyed by a high temperature.
14.5 Ester vapour rises and condenses on the cooler glass surface and runs back down into the liquid below.
This refluxes the upflowing vapour.
14.6 Sodium carbonate is a base which neutralises the sulfuric and ethanoic acids.
14.7 Smaller molecules are more soluble in water. The O atom in the ester can form hydrogen bonds with water.
As the ester gets larger, its non-polar alkyl ( C and H ) chain gets longer and this makes it less water-soluble.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 98 of 107
 Organic Molecules - Chemical Reactions Past Matric Papers Memorandum
15. C ( Questions from Page 88 - 89 )
16.
16.1 Prop-1-ene is highly flammable.
because it burns quickly and easily due to its high volatility as it evaporates very easily and thus it can be explosive.
16.2 Alkenes contain a double carbon – carbon ( C=C) bond. The presence of the pi double bond makes them
unsaturated as all the carbon atoms are not bonded to the maximum number of atoms.

16.3.1 H H H H H H
I I I H H I I I
H— C— C = C + O → H—C—C—C—H
I I I I I
H H H O H
H

16.3.2 Hydration
16.3.3 Sulphuric acid H2SO4 OR Phosphoric acid ( H3PO4 ). Any other acid NOT accepted.
16.4 C3H8 + 5 O2 → 3 CO2 + 4 H2O

16.5 H H H H H
I I I concentrated H2SO4 I H H
H–C –C–C–H → C =C–C–H + O
I I I ∆ I I
O H H H H H
H

Functional group encircled. Primary alcohol has the OH attached to a C that is only attached to one other C.
16.6 Dehydration

17.1 D If there is limited O2 then instead of CO2 forming, CO or C ( smoky soot ) will form
17.2 C Alcohol : ethanol is represented in the ester name as ethyl.
Acid : methanoic acid is represented in the ester name as methanoate.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Reactions Past Matric Papers MEMORANDUM Page 98 of 106
 TOPIC : Organic Chemistry - Plastics and Polymers NOTES
Making a polymer from ethene molecules
Monomers are small organic molecules that can be covalently bonded to each other in a repeating pattern.

H H H H H H H H H H
H H I I I I I I I I I I
ethene monomer C=C → ‒C‒C‒ ‒C‒C‒ + ‒C‒C‒ → ‒C‒C‒ C‒C‒
H H I I I I I I I I I I
H H H H H H H H H H
repeat unit

The double bond of the monomer snaps to form a repeat unit. chain growth

Polymerisation is the chemical reaction in which monomer molecules join to form a polymer.

repeat unit
repeating chain
H H H H H H H H H H H H
I I I I I I I I I I I I
‒C‒C‒C‒C‒ + ‒C‒C‒ → ‒C‒C‒C‒C‒C‒C‒
I I I I I I I I I I I I
H H H H H H H H H H H H
The double bonds snap to form two unpaired electrons and in this free radical state new bonds can keep form-
ing with identical neighbouring molecular fragments that are also free radicals as they have one or more
unpaired electrons.
The repeat units link up
like a string of beads.

+ repeating chain

Each time a repeat unit adds on,

the repeating chain grows longer

We represent the polythene polymer as

H H H H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I I I I
‒C‒ C‒C‒C‒C‒C‒ + ‒C‒C‒ → ‒C‒C‒C‒C‒C‒C‒C‒C‒ ‒C‒C‒
I I I I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H H H H n

This is a chain-growth or addition polymer.

[ H2 C ‒ C H2 ]
n
A polymer is a large molecule composed of smaller monomer units covalently bonded to each other in a
repeating pattern.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Page 100 of 107
 Organic Chemistry - Plastics and Polymers NOTES
Addition polymer isation
is a reaction in which small molecules join to form very large molecules by adding on double bonds.

polythene or polyethylene

A macromolecule is a molecule that consists of a large number of atoms.

The final macromolecule polymer is called polythene or polyethylene. ( poly means many ethenes )
Polythene is only useful if the molecular mass is about 1 million ( tens of thousands of atoms linked )
which is achieved by heating the reaction at 200ºC - 300 ºC and 1 200 - 2 000 atmospheres of pressure to limit
side branches forming.
The many side branches that do form prevent close packing of the polymers and this process makes low density
polythene ( LDPE ).
An addition polymer is a polymer formed when monomers ( usually containing a double bond ) combine
through an addition reaction.

Polyethylene, world wide, is the most popular plastic as it is cheap, flexible, durable and chemically resistant.
Some uses of LDPE ( low density polyethylene )

make milk containers

sandwich plastic bags cling wrap plastic toys moisture proof

moulded plastic
electrical insulators plastic crates squeeze bottles objects

Polythene is the most common plastic and makes the familiar supermarket plastic bags, thin plastic films and
sheets and squeeze bottles, packaging materials, moulded objects and electrical insulation, cling wrap for
protecting food.
Its recycling number is
4
LDPE
We write the polymerization reaction as
n CH2 = CH2 → ‒ CH2 ‒ CH2 ‒ n
monomers polymer where n is a big number.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Page 101 of 107
 Organic Chemistry - Plastics and Polymers NOTES
High density polythene.
Using a catalyst at 60ºC and 1 atmosphere pressure allows few side branches to form as the ethene
molecules snap their double bonds and add on to the end of the chain where the ions of the catalyst are.
These polymers thus tend to be long straight chains, with few side chains, that can pack together closely to form
hard and rigid plastic crates, car fittings and pipes.
In this compact form the polymer is called high density polythene. HDPE. 2 is the recycling number.
HDPE

water pipes garbage bins milk jug

toys

HDPE storm drainage pipeline

( Wikipedia )

Addition polymer The CH2 = CH‒ group is called a vinyl group.

PVC Polyvinyl chloride ( ethene is called vinyl when atoms are attached to a C- atom in the place of H )
H H polymer monomer monomer
I I H H H H
C‒C‒ I I chloroethene I I
‒ CH2 CH ‒ C ‒ C ‒
I I n or vinyl chloride C = C OR CH2 = CH
I I I
H Cℓ Cℓ I I I
n H Cℓ H Cℓ Cℓ
poly ( chloroethene ) repeat unit a section of the PVC polymer chain
H H H H H H H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I I I I I I 3
‒ C ‒ C ‒ C ‒ C ‒ C ‒ C C ‒ C ‒ C ‒ C ‒ C ‒ C ‒ C ‒ C ‒C ‒ C ‒ C ‒ C C ‒ C ‒
I I I I I I I I I I I I I I I I v
I I I I
H Cℓ H Cℓ H Cℓ H Cℓ H Cℓ H H Cℓ H Cℓ H Cℓ H Cℓ H Cℓ Recycle number
To participate in polymerisation, the vinyl chloride monomer molecule must be able to react at both ends.

Cℓ Cℓ Cℓ Cℓ Cℓ Cℓ Cℓ Cℓ
Cℓ Cℓ

PVC gutters
gluing PVC plastic PVC conduit pipes that protect
floor tiles electrical wiring in a house rain water

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Page 102 of 107
 Organic Chemistry - Plastics and Polymers NOTES
Polyesters are formed by step-growth or condensation polymerisation.
Condensation polymerisation occurs when molecules of two monomers with different functional
groups undergo condensation reactions with the loss of small molecules, usually water.

A molecule with two alcohol functional groups reacts with a molecule that has two carboxylic acid functional groups.
A water molecule is eliminated, for example, if ethan-1,2-diol reacts with ethandioic acid

H H monomer O O monomer H H O O
I I II II I I II II
H‒O‒C‒C‒O‒H H‒O‒C‒C‒O‒H → H‒O‒C‒C‒O ‒C‒C‒O‒H + H2O
I I I I
H H H H dimer or copolymer
Copolymer
is a polymer derived from two monomeric species ( made of one part only.because “mer” means a “ part “ )
The dimer molecules must line up alternately with the acid group next to an alcohol group to undergo elimination

A condensation polymer is a polymer formed H H O O

by two monomers with different functional groups I I II II
that are linked together in a condensation reaction ‒O‒C‒C‒O ‒C‒C ‒
in which a small molecule, usually water, is lost. I I
H H n polyester

Mylar is a polyester that makes thin films like space blankets which are thin layers of tough plastic on either side of
aluminium foil. The aluminium foil reflects back the body heat to keep the person warm.
Kevlar polyester fibres make bullet proof vests.
A polycarbonate polyester makes Lexan which is tough and transparent and acts as shatter-proof glass and
motor bike riders' helmets and visors ( a surface which protects the eyes ).

bullet

Mylar outdoor space blanket. Kevlar bullet-proof vest Lexan helmet and visor

Polylactic acid ( PLA ) is a bioplastic and biodegrades mealie

PLA is produced by fermentation of cor n ( mealies ).
Lactic acid forms which has both an OH and a COOH functional group. .
PLA is used for food and cosmetic packaging, agricultural sheeting and household appliances.
Plastic polymers cannot be economically recycled like metals, so disposal is a problem.
But PLA is the one plastic that is biodegradable by the enzymes in bacteria.
The package which keeps the hamburger warm is
made from PLA

hamburger
City dumps are full of plastic waste.
One million sea birds die each year when they try to eat plastic and choke to death.
100 000 sea mammals die each year by eating and choking on plastic or getting tangled up in plastic nets and
drowning.
dolphin

seagull sea cow whale

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Page 103 of 107
 Organic Chemistry - Plastics and Polymers Activities 4
1. ( Memo Page 106 )
1.1
Write a formula to explain what an ethene molecule looks like when its double bond snaps.
H H
ethene monomer
C=C →
H H
1.2 What does it look like if a number of ethene double bonds snap and these snapped bonds join up with each
other?
1.3 What name do we give to a polymer if it consists of thousands of ethene molecules that have joined together
after snapping their double bonds?

1.4 What is the usual way for writing the formula of a long polythene polymer or macromolecule?
1.5 What does the n stand for in the formula of a polymer?

1.6 How do we deduce the formula of the monomer that is the basis of the polythene polymer?

2.
2.1
Write a formula to explain what a chloroethene molecule looks like when its double bond snaps.
H Cℓ
C=C →
H H
2.2 What does it look like if a number of chloroethene double bonds snap and these snapped bonds join up with
each other?
2.3 What name do we give to a polymer if it consists of thousands of chloroethene molecules that have joined
together after snapping their double bonds?
2.4 What is the usual way for writing the formula of a long polyvinyl chloride polymer?

2.5.1 What does the word vinyl refer to?

2.5.2 Write a structural formula for the vinyl functional group.

2.5.3 Write a formula for vinyl chloride.

2.6 How do we deduce the formula of the monomer that is the basis of the polyvinyl chloride polymer ( PVC )?

3.
The following is a fragment from a long polymer :

F F F F F F F F F F
I I I I I I I I I I
C ‒ C ‒C ‒ C C ‒ C ‒ C ‒ C ‒C ‒ C ‒
I I I I I I I I I I
F F F F F F F F F F

3.1 Write the formula of the repeat unit.

3.2 Write the formula of the polymer in two different ways.

3.3 Write down the formula of the monomer that produces this polymer. Name this monomer.

3.4 Name this polymer.

3.5 What type of polymerization produces this polymer, addition or condensation?

3.6 Mention two uses for this polymer.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Activities 4 Page 104 of 107
 Organic Chemistry - Polymers Past Matric Papers
( Memo Page 107 )
1.1 Cracking is a process that is generally used in the oil industry.

1.1.1 What is meant by cracking? (2)

1.1.2 Why is cracking used in the fuel industry? (2)

1.1.3 Give a reason for the difference in the melting and boiling points of the following two compounds,
produced from a specific cracking process:

COMPOUND MELTING POINT (˚C) BOILING POINT (˚C)

Butane ‒138 ‒1
Heptane ‒91 89 (2)

1.2 In which phase (gas, liquid or solid) is each of the following when used as a fuel:

1.2.1 Butane

1.2.2 Heptane (2)

1.3 Which ONE of the following reaction types can be used to prepare ethene from octane?
A Addition
B Hydrogenation
C Cracking
D Substitution

1.4 The reaction type that can be used to convert hydrocarbons with high molecular masses to hydrocarbons
with low molecular masses (1)

2. Petrol requires alkanes in the range from C5 to C10. Cracking is the process that is used to convert longer
chains into shorter chains. The diagram below illustrates one of the possible cracking reactions of C15H32

H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
H‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒H
I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H

high temperature high pressure

H H H H H H H H H H H H
I I I I I I I I I I I I
C=C + C=C + Y + H‒C‒C‒C‒C‒C‒C‒C‒C‒H
I I I I I I I I I I I I
H H H H H H H H H H H H

Write down the STRUCTURAL FORMULA and NAME for the hydrocarbon represented by Y.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Past Matric Papers Page 105 of 107
 Organic Chemistry - Polymers Activities 4 Memorandum
( Questions from Page 104 )
H H H H 1.2
1.1 H H H H H H
C=C I I
H H → ‒C‒C‒ I I I I I I
I I ‒C‒C‒C‒C‒C‒C‒
H H I I I I I I
H H H H H H
1.3 Polythene or polyethene or polyethelene.
1.4 H H 1.5 A very big number. 1.6 Remove the n and the square brackets and
I I use the two unattached horizontal bonds to reform
C‒C the original double bond.
I I H H H H
H H n I I I I
C‒C C=C
2.1 I I I I
H H n H H
H H
H H
I I 2.2 H H H H H H
C=C
→ ‒C‒C‒ I I I I I I
H Cℓ
I I ‒C‒C‒C‒C‒C‒C‒
H Cℓ I I I I I I
H Cℓ H Cℓ H Cℓ
2.3 Polytvinyl chloride

2.4 H H 2.5.1 Vinyl means an ethene molecule has lost a hydrogen atom.
I I
C‒C 2.5.2
H H
I I
C=C vinyl functional group
H Cℓ n H

2.5.3
H H
Vinyl chloride means that a chlorine atom has replaced the hydrogen
C=C vinyl chloride
atom in ethene.
H Cℓ

2.6 Remove the n and the square brackets and use the two unattached horizontal bonds to reform the original
double bond. H H H H
I I I I
C‒C C=C vinyl chloride monomer
I I I I
H Cℓ n H Cℓ

3.1 3.2
F F 3.3
F F F F
I I I I
C‒C‒ I I
C ‒ C ‒ polymer tetrafluoroethene
I I C=C
I I I I
F F F F F F
n
repeat unit
‒ CF2 CF2 ‒ monomer
n

3.4 Teflon polytetrafluoroethene 3.5 addition

PTFE
3.6 Its surface is smoothest and needs no lubrication. So it makes low friction sliders that are fitted under objects
if they are to be moved around, like cupboards or chairs and sofas in a lounge.
Non-stick pans are coated with teflon.
Makes a stain repellent for carpets and clothes as it does not react with anything.

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Activities 4 MEMORANDUM Page 106 of 107
 Organic Chemistry - Polymers Past Matric Papers
1.1 Memorandum ( Questions from Page 105 )
1.1.1 Dividing longer chains of hydrocarbons into shorter chains
1.1.2 To obtain a larger percentage usable products from larger fractions crude oil. Shorter chains which bur n
more evenly. Shorter chains are blended with fuel to enrich fuel
1.1.3 Boiling point increases with increasing molecular mass.
Van der Waals forces increase with increasing molecular mass.
1.2 1.2.1 gas 1.2.2 liquid 1.3 C 1.4 cracking
2. H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
H C‒C• •C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒H →
••

I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H
An electron-pair bond breaks. Each C atom keeps one electron’.
H•
One H atom with its electron moves to the other chain, leaving an unpaired electron
behind.
H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
• C‒C• H C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒H →
••

I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H

The two unpaired electrons form a double bond, the ethene molecule.

H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
C=C H‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒H →
I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H

We are told that this process repeats itself to form another ethene molecule.
This leaves a chain of 11 carbon atoms

H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
C=C C=C H‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒C‒H →
I I I I I I I I I I I I I I I
H H H H H H H H H H H H H H H

This longest chain has another bond that snaps to leave a chain of 8 carbon atoms
H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
C=C C=C H‒C‒C‒C‒C‒C‒C‒C‒C• • C‒C‒C‒H →
I I I I I I I I I I I I I •• I
H H H H H H H H H H H H H H H

A H atom and its electron transfer across the broken bond. H•

H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
C=C C=C H‒C‒C‒C‒C‒C‒C‒C‒C H • C‒C‒C‒H →
••

I I I I I I I I I I I I I • I
H H H H H H H H H H H H H H

The two unpaired electrons unite to form a double bond.

H H H H H H H H H H H H H H H
I I I I I I I I I I I I I I I
C=C C=C H‒C‒C‒C‒C‒C‒C‒C‒C‒H C=C‒C‒H →
I I I I I I I I I I I I I I
H H H H H H H H H H H H H H propene

F PT S 2410 Physical Sciences TDP Gr 10-12 Organic Chemistry Polymers Past Matric Papers MEMORANDUM Page 107 of 107