PHYSICAL SCIENCES

GRADE 12
TOPIC:MATTER AND MATERIALS
ORGANIC MOLECULES

CURRICULUM SUPPORT SERVICE

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2
 MATTER AND MATERIALS:
ORGANIC CHEMISTRY

Key concepts to be learnt:

1.Defining organic molecules

2. Naming of organic compounds

3. Types of reactions in organic compounds

4. Physical properties of organic compounds

•NB: Key words should be taken into consideration in definitions.

x Definitions should be written as they appear in the Examination Guidelines .
 Definitions
• Organic molecules as molecules containing carbon
atoms
• Molecular formula is a chemical formular that indicates
the elements and numbers of each of the atoms in a
molecule. Example
• Structural formula is a compound shows which atoms
are attached to which within the molecule. Atoms are
represented by their chemical symbols and lines
5
 Activity
Give definitions of the following:
1.Organic molecules
2.Hydrocarbons
3.Functional group
4.Homologous series
5.Saturated Compounds
6.Unsaturated Compounds.
NB. Teacher should give more
activities for each concept.
Homologous Series, Functional Groups and
General Formulae.

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Activity

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 Type of structural isomers:
Organic molecules with the same molecular formula, but
different structural formulae.
• Restrict structural isomers to chain isomers, positional
isomers and functional isomers.
• Chain isomers: Same molecular formula, but
different types of chains, e.g. butane and 2-
methylpropane.
• Positional isomers: Same molecular formula, but
different positions of the side chain, substituents or
functional groups on the parent chain, e.g. 1-
chloropropane and 2-chloropropane or but-2-ene
and but-1-ene.
• Functional isomers: Same molecular formula, but
different functional groups, e.g. methyl methanoate
and ethanoic acid, Propanal and Propan – 2 - one
Examples of structural Isomers
1. Chain Isomers
Chain Isomers
2. Positional Isomers
eg. Positional Isomers of Pentan – 2 – ol
 Positional Isomers
eg. Positional isomers of butene:
 Functional Isomers examples
• Butanal

• Butan – 2 – one

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Activity

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Functional isomers of Carboxylic
acids and esters
• Butanoic acid

• Ethylethanoate

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Examples of functional
Isomers
Activity

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 NAMING OF ORGANIC COMPOUNDS

Step 1: Examine the molecule and the

number of carbon atoms it contains
1.1 Identify the longest continuous carbon chain
(longest chain can include the double or triple
bond or functional group)
NB The chain is not always straight.
1.2 Identify the functional groups, and branches
(side chains) attached to this chain
NAMING OF ORGANIC COMPOUNDS

1.3. Name the longest continuous carbon

chain (longest chain must include the
double or triple bond or functional group)
1.3 Start numbering closest to the
functional group or the side chain.

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NAMING OF ORGANIC COMPOUNDS

1.3.1 Note that functional group, double

and triple bonds have the lowest number.
1.3.2 Chains are numbered so that the
largest side chains (branch) have the
lowest numbers.
1.3.3 Halo-groups named in alphabetical
order: bromo-, chloro-, fluoro-, and iodo

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 NAMING OF ORGANIC COMPOUNDS

1.3.4. Halogen substituents do not get

preference over Alkyl Groups.( And Alkyl
Group do not get preference over Halogen)
1.3.5. When substituents, e.g. Br and Cℓ or
Cℓ , and have the methyl same number
when numbered from different ends of
chain, preference is given to alphabetical
order, e.g. bromo- over chloro-; chloro- over
methyl-.
 NAMING OF ORGANIC COMPOUNDS

1.3.6. When writing IUPAC names,

substituents are written alphabetically
namely bromo, chloro, ethyl, methyl. Ignore
prefixes di and tri.
1.3.7. If two or more identical alky group
( Identical substituent) are present:
1.3.8. Use a suitable Greek prefix, such as
di, tri, tetra etc to indicate the position of the
identical substituent.
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 Naming organic molecules
2. Apart from that each substituent is given a
number depending on its position on the main
chain.
3. The numbers which indicate the positions are
separated by commas, preceded by prefix di,
tri, tetra
4. Numbers are separated by hyphens.
5. If two identical substituents are attached to the
same carbon atom, the number is used twice.
Prefixes
Naming the molecules
 Functional group and multiple bonds are
indicated by suffixes. See table below

 In the case of alkenes (double bonds present)

or alkynes (triple bonds present) we add the
suffix “-ene” or “-yne” respectively. E.g. but-1-
ene
Naming of organic molecules
Naming of organic molecules
Naming of Organic molecules
 Class activities 1,2,3 and 4
Write the IUPAC names of the following
organic molecules.
 Organic Structures
• Answers to the activity above:
• Structure 4 – 3 – 1 – 2
• 1. 4-bromo-2-methylhexane
• 2. 3-bromo – 2 – chloro – 4 –
methylpentane
• 3. 2 – bromo – 4 – chloro – 3 -
methylpentane
• 4. 2-bromo-4-chloro-4-methylpentane
 Ketones and Aldehydes
• Ketones and Aldehydes are
compounds that contain carbonyl group
an oxygen is attached to
carbon atom with the help of double bond
in a compound.
They are functional isomer with the same
general formula of .

36
 Aldehydes
• Aldehydes are organic molecules which
at least contains one Hydrogen on the
carbonyl group.

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 Naming of Aldehydes
• When naming Aldehydes numbering
start next to the carbonyl group.
• The name of the parent chain should
have the carbonyl group.
• The name of aldehyde take the suffix al
at the end.

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Example of naming aldehydes

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 Ketones

• Ketones are organic molecules has

two organic compounds attached to the
carbon on the carbonyl group.

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 Naming Ketones
• Ketones end with the suffix one.
• The parent chain should have the
carbonyl group, number starts next to
the functional group.

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Activity Naming Organic

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 Using the above information:
Write down the LETTER that represents EACH of the following:
1.1. Aldehyde (1)
1.2. Ketone (1)
1.4. Functional isomer of B. (1)
2. Write down IUPAC Names of:
2.1. Compoud B (1)
2.2. Compoud E (4)
3. Define positional isomers. (2)
4. Write down the STRUCTURAL FORMULA of:
4.1. A positional isomer of compound C (2)
4.2. Compound D (2)

NB. Teacher give more activities for

each topic
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Organic molecules reactions

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 TYPES OF REACTIONS IN ORGANIC COMPOUNDS
 Organic compounds undergo different reactions depending on
whether the compound is saturated or not, the compound it is
reacting with and the conditions under which the reaction is
taking place.
Alkanes undergo the following reactions:
• Combustion (or oxidation)
• Substitution
• Elimination
Alkenes undergo the following reactions:
• Combustion (or oxidation)
• Addition
 TYPES OF REACTIONS IN ORGANIC
COMPOUNDS
Alkynes undergo the following reactions:
• Combustion (or oxidation) reactions
• Addition reactions
Haloalkanes undergo the following reactions:
• Substitution
• Elimination
Alcohols undergo the following reactions:
• Substitution
• Elimination

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 Application of Organic Chemistry:
Combustion Reactions
Combustion/ Oxidation is reactions of
hydrocarbons (Alkanes, Alkenes and
Alkynes) with oxygen.
Alkanes
 Alkenes
Alkynes
Oxygen is always in excess.

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 Alkanes

1.
1st Step: Balance the n both sides.

2nd Step: Balance nboth sides.

3rd Step: Balance nboth sides.

Now the equation is balanced.

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 Alkenes

2.
1st Step: Balance the n both sides.

2nd Step: Balance nboth sides.

3rd Step: Balance nboth sides.

Now the equation is balanced

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 Alkynes

1.
1st Step: Balance the n both sides.

2nd Step: Balance nboth sides.

3rd Step: Balance nboth sides.

Now the equation is balanced.

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 Activity
1. Write the reaction and products of the
following:
1.1. The combustion of Pentane in excess
oxygen.
1.2. When butane is burning in excess
oxygen.
1.3. When ethene is burning in excess
oxygen.
NB. Teacher give more activities for each
topic
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 Application of Organic Chemistry:
Esterification
• Ester is organic compound that is
formed during reaction between
Carboxylic acid(s) and Alcohol(s).
• General formular of
• And esters and carboxylic acids forms
functional isomers.
• It is a condensation reaction is
eliminated.

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 Application of Organic Chemistry:
Esterification
• is formed from removedfrom the acid
and from the alcohol.
• Very slow reaction, unless! an
acid catalyst used (usually
sulphuric acid)
• General formula is:

• Names of esters end in –oate.

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 Names of esters end
Naming in –oate.

Named after alcohol & carboxylic acid

from which they are derived.
O
C CH3
CH3 CH2 O
ethyl ethanoate

this part comes from this part from the

the alcohol & is acid and is named
named after it after it
 Structural
formulae
Although the previous structural formula
are the clearest way of showing esters,
they can draw out in a shortened form.
In this
version the
ethyl ethanoate acid part
Or…
O has been
O
written first
CH3 C O CH2 CH3
CH3 CH2 O C CH3
 Identify the group attached to the C=O –
this is from the acid
 The group attached to the –O- is from the
alcohol.
Structural formulae

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Structural formulae

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 Smell of Esters
• Esters have strong, sweet smells.
• Their bouquet is often floral or
fruity.
• This means they are used in food
flavourings & perfumes.
• Also, very good at dissolving
organic compounds so often used
as solvents.

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 Activity
Redraw and comple the table
Alcohol Acid Ester Structural formula

Propanol Ethanoic acid

Ethanol Ethyl Pentanoate

Methanoic Butyl Methanoate

acid

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 ADDITION REACTIONS
There are four types of addition
reactions and these only occur in
unsaturated compounds.
1. Hydrohalogenation
2. Halogenation
3. Hydration
4. Hydrogenation
 Hydrohalogenation

• In hydrohalogenation and hydration there is a special

rule (Markovnikov’s Rule) that must be used:
“The H-atom joins to the C-atom of the double bond that
already has the most H-atoms attached to it.”
1.1 the addition of a compound consisting of hydrogen
and a halide ion such as I- , Cl- , Br- , etc - i.e. the
addition of HX
1.2. Halogen atoms and hydrogen atoms are added into
the original molecule
1.3 Example:

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Reaction conditions for hydrohalogenation
When the HX (X = Cl, Br, I) is added to the
alkene, no water must be present
 Addition HX to unsaturated hydrocarbons – the
H atom attaches to the C-atom already having
the greater number of hydrogen atoms
(Markovnikov’s rule) and the X attaches to the C-
atom having fewer hydrogen atoms (use propene
/ butene to illustrate this rule)
Example of Hydrohalogenation

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Example of Hydrohalogenation

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 Halogenation (Addition)
This reaction occurs easily and does
not require a catalyst.
It is a addition of halogen to
unsaturated hydrocarbon.

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 Reaction conditions
• is dissolved in non – polar solvent.
• No water should be present.
• Catalyst is not needed.
• The reaction is spontaneous
• It occurs at room temperature

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 Examples of Halogenation
• Bromination of 1-propene to form 1,2-
H
dibromopropane
CH Br Br
3

C C + Br Br H C C CH3
H H
H H
• Chlorination of trans-2-butene to form
2,3-dichlorobutane
Cl Cl
H CH3
C C + Cl Cl H3C C C CH3
H3C H
H H
Examples of halogenation

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Examples of halogenation

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 Hydration
The addition of as reactant to alkenes

The H-atom attaches to the C-atom

already having the greater number of H-
atoms (Markovnikov’s rule) and the OH
group attaches to the more substituted C-
atom (use pronene / butene to illustrate
this rule)

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 Reaction conditions for hydration:

 in excess, added to alkene

Small amount of can be used as a
catalyst during this addition
reaction.

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Hydration

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Hydration

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 Hydrogenation
The addition of to alkenes
• →
The addition of to alkynes
•

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 Reaction conditions for
hydrogenation:
in excess ( atmosphere), added to
alkene or alkyne
 Alkene/alkyne dissolved in a non-polar
solvent with catalyst (Pt, Pd or Ni)

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Hydrogenation

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Hydrogenation

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 Activity
1.1. What is addition reaction
1.2. Name the homologous series of
which compounds undergo addition
reaction.
1.3.Name four types of addition reaction.

NB. Teacher give more activities for

each topic

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 ELIMINATION REACTIONS
Saturated compounds namely
• haloalkanes,
• alcohols and
• alkanes undergo elimination reactions.
Elimination reactions are the reverse of
addition reactions
Something is removed from a substance
So, one single compound forms two
compounds

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 Types of elimination reactions:

Dehydrohalogenation
Dehydration
Cracking of alkanes

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 Dehydrohalogenation:
• The removal of a hydrohalide, HX, from
a haloalkane, forming an alkene

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 Reaction conditions:
• Heat under reflux (vapours condensate and
return to reaction vessel during heating)
• • Heat strongly in concentrated NaOH or KOH
solution in pure ethanol as the solvent
• • If more than one elimination product is
possible, the major product is one where the
H-atom is removed from the C-atom with the
least number of H atoms (Zaitzev’s Rule )

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Dehydrohalogenation

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Dehydrohalogenation

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Dehydrohalogenation

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 Dehydration
• The removal of from an alcohol
• An alkene forms

86
 Reaction conditions for
dehydration
• Reaction is an acid catalysed dehydration reaction –
the alcohol is heated with an excess of conc. H2SO4
(or H3PO4)
• • To produce a gaseous alkene (ethene) easier – use
ethanol vapour that is passed over heated Al2O3
powder
• • If more than one elimination product is possible, the
major product is one where the H atom is removed
from the C-atom with the least number of H atoms (an
alkene with the more highly substituted double bond is
the major product)

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Dehydration

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 Cracking
• A process where by longer chain
hydrocarbon molecule is broken into
shorter and more useful molecules.
• Two types of cracking :
• Thermal and Catalytic Cracking.

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 Thermal Cracking
• Is a cracking of hydrocarbon under
condition of high pressure and
temperature, without using catalyst to
break down the larger fraction of cruide
oil into useful molecules.
• Reaction conditions:
• Higher temperature (800+
• Higher pressure (700+atm)

90
Examples of Thermal
Cracking

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Thermal Cracking

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 Activity
1.1. What is elimination?
1.2. Name the homologous series of
which undergo elimination.
1.3. Name the type of elimination that:
1.3.1. HX is eliminated
1.3.2. is eliminated.
1.3.3. Larger molecules are broken down
into smaller molecules.
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 Substitution reaction
• Is a chemical reaction in which an atom or
group of atoms in a molecule are displaced
by another atom or group of atoms.
• Substitution occurs on:
Alkanes Haloalkane
Alcohols
 Haloalkanes dilute strong base Alcohol +
Salt + Heat.
Haloalkane + O Alcohol +
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 Substitution reaction
• Alkanes Haloalkane
• Reaction conditions:
Heat or Sunlight (UV Light).

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Alkanes Haloalkane

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Alkanes Haloalkane

97
Alkane + Haloalkane + HX

98
 Substitution reaction
• Alcohols HaloalkaneO
• Reaction conditions:
 For tertiary alcohols HBr or HCL is added
directly at room temperature.
 For primary and secondary alcohols,
Solid NaBr or KBr + (Sulphiric acid is used
to make HBr in a reaction flask.
 HBr react slowly and it must be heated.

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Substitution reaction

100
Substitution reaction

101
Substitution reaction

102
 1st Method
•
• Reaction conditions:
 Diluted strong base (LiOH, KOH or
NaOH) NB, Base should be in aqueous
solution. Strong base causes elimination
 Haloalkane should be dissolved in
ethanol and heat the mixture
moderately

103
1 Method
st

104
1 Method
st

105
 2 Method
nd

• Reaction condition:
 Add excess water.
 Dissolve the Haloalkane in ethanol
and heat moderately.

106
2 Method
nd

107
2 Method
nd

108
 Activities for consolidating
reactions
Identify the types of reaction taking place in A,B,C,D
and E

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Physical properties

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Physical properties
of organic molecules
 Boiling point
What is boiling point?

Temperature at which the vapour pressure of a

substance is equal to the atmospheric
pressure.

(The stronger the intermolecular forces, the

higher the boiling point)
 Melting point
What is melting point?

• The temperature at which the solid and liquid

phases of a substance are at equilibrium.

• (The stronger the intermolecular forces, the

higher the melting point)
 Vapour pressure
What is vapour pressure?

The pressure exerted by a vapour at

equilibrium with its liquid in a closed
system.

(The stronger the intermolecular forces,

the lower the vapour pressure)
 Intermolecular forces
The stronger the intermolecular force the higher the
boiling point and melting point, lower vapour
pressure
London Dipole dipole Hydrogen bonds
forces forces

Alkanes Aldehydes Alcohols ( 1 )

Alkenes Ketones Carboxylic acids ( 2)
Alkynes Halo- alkanes
Esters
116
 SITES FOR HYDROGEN
BOND
• Alcohols have 1(one) site for Hydrogen Bond

• Carboxylic Acids have 2(two) sites for

Hydrogen Bond.
 Factors influencing physical
properties
• Functional group

• Chain length

• Branching of the chain

Type of functional group
 Polarity of functional group

H H H H
H H H H H
H C C C C O
H C C C C C H
H H H H H
H H H H H
butanal

H H H O

H C C C C

H H H H
pentane butan-1-ol
 carboxylic alcohol Ketone ~ aldehyde ester
acid

H
O O O
R C O O
R H H R C R R C R C O
C O H
H R

Decreasing polarity of functional groups

alkane

CnH2n+2
Number of functional groups
 Number of functional groups

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

ethanol ethan-1,2-diol
Surface area - chain length
 Surface area - chain length

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

pentane
H H H H H H H H
H C C C H H C C C C C H
H H H H H H H H
propane butane
Surface area - branching
 Surface area - branching

de
c re
as
ei
ns
urf
ac
ea
r ea

pentane

2,3-dimethylpropane

1-methylbutane
 Exercise 1
Give IUPAC names & explain the difference in boiling points.
H H H H
H
H C C C C Cl H H C H
H H H H H C C Cl
b.p. 78 °C
H H C H

b.p. 51 °C H
 Exercise 1: answer H
b.p. 51 °C
b.p. 78 °C
H H C H
H H H H
H C C Cl
H C C C C Cl
H H C H
H H H H 2-chloro-2-methylpropane
1-chlorobutane
H
The BRANCHED HYDROCARBON, 2-chloro-2-methylpropane,
will have LESS SURFACE AREA, and thus weaker
intermolecular attractions than the straight-chain
hydrocarbon, 1-chlorobutane.
 Exercise 2
Give IUPAC names & explain the difference in boiling points.
H H H H

H H H H H C C C C H
H
H C C C C O H H O H
H H C H H
H H H H H H
100 °C
H C C C H
118 °C
H O H
H
81 – 83 °C
 Exercise 2: answer
Give IUPAC names & explain the difference in boiling points.
H H H H
H H H H
H C C C C H
H C C C C O H

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

H O H
H
2-methylpropan-2-ol
 Exercise 2: answer
• Butan-1-ol is a primary alcohol
• Butan-2-ol is a secondary alcohol
• 2-methylpropan-2-ol is a tertiary alcohol
• There is a increase in the branching of the
chain and therefore weaker intermolecular
forces (Van der Waals) resulting in a decrease
in the boiling point from butan-1-ol to butan-2-
ol to 2-methylpropan-2-ol.
• The least energy is needed to break the Van
der Waals forces between methylpropan-2-ol
molecules and therefore its boiling point is the
lowest.
 butan-1-ol

Decreasing boiling point

butan-2-ol

2-methylpropan-2-ol
 Exercise 3

Draw the structural formulae for each of the

following
compounds and predict which one will have
the
highest melting point .

3.1 but-2-yne

3.2 hex-2-yne

3.3 pent-2-yne
 Exercise 3: answer
H H H H H H

3.1 but-2-yne H C C C C H 3.2 hex-2-yneH C C C C C C H

H H H H H H

H H H

C C C C
3.3 pent-2-yneH C H

H H H

All three compounds are alkynes. There is an increase in chain

length with
but-2-yne having the shortest chain and hex-2-yne the longest.
The Van der Waals forces (London forces) will be stronger in the
longest chain compound, hex-2-yne, because it has more sites
for London forces to act.
Hex-2-yne will therefore have the highest melting point as the
molecules will stick together more.
 Exercise 4
Draw the condensed structural formula for each compound
& explain the difference in vapour pressure.

4.1 propanoic acid (vp = 0,5 kPa at

20oC)

4.2 butan-1-ol (vp = 5,4 kPa at 20oC)

 Exercise 4: answer

4.1 CH3CH2COOH
4.2 CH3CH2CH2CH2OH

Both compounds have the same molecular mass,

but butan-1-ol is less polar than propanoic acid.
Propanoic acid has two sites for hydrogen
bonding, but butan-1-ol has only one.
Butan-1-ol therefore has weaker intermolecular
forces (hydrogen bonds) and will go into the
vapour phase easier than propanoic acid.
Butan-1-ol therefore has a higher vapour
pressure than propanoic acid.
 B
• Because B has a longer • A – Propane
chain length than C • B – Pentane
then its surface area is
high. • C - Butane
• The intermolecular
forces in B will be
stronger than in C
• Much energy is needed
to overcome the
stronger Intermolecular
forces in B
 Acknowledgement of resources
• Theory and Workbook by Olivier book 2
(Organic Chemistyry).
• Physical Sciences Solution for all grade
12.
• Physical Sciences Docscientia Book 2.
• NB. Teacher give more activities for
each topic

139