Organic

Chemistry
Introduction
Organic Chemistry

What do I
need to know
about organic
chemistry?
 Organic Chemistry
Overview
In the nineteenth century, chemists believed that all organic chemicals
originated in tissues of living organisms. Friedrich Wohler, in 1828,
challenged this belief and synthesised the organic compound urea, a
compound found in urine, under laboratory conditions. His work led
other chemists to attempt the synthesis of other organic compounds.
In this section, students examine the sources of fuels, some basic
concepts of organic chemistry such as homologous series, functional
group, general formula and structural formula, and polymers. Students
should be able to identify and name unbranched alkanes, alkenes,
alcohols and carboxylic acids. They should recognise that materials
such as plastics, detergents and medicines, and even the food that we
eat are examples of organic compounds. Students should be able to
value the need for assessing the impacts of the use of synthetic
materials and the environmental issues related to the use of plastics.
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 Ministry of Education Singapore
 Organic Chemistry
Learning Outcomes:
Candidates should be able to:
Fuels and Crude Oil
a) Name natural gas, mainly methane, and petroleum as sources of energy.
b) Describe petroleum as a mixture of hydrocarbons and its separation into
useful fractions by fractional distillation.
c) Name the following fractions and state their uses:
i) Petrol (gasoline) as a fuel in cars.
ii) Naphtha as feedstock for the chemical industry.
iii) Paraffin (kerosene) as a fuel for heating and cooking and for aircraft
engines.
iv) Diesel as a fuel for diesel engines.
v) Lubricating oils as lubricants and as a sources of polishes and waxes.
vi) Bitumen for making road surfaces.

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 Organic Chemistry
d) State that the naphtha fraction from crude oil is the main source of
hydrocarbons used as the feedstock for the production of a wide range of
organic compounds.
e) Describe the issues relating to the competing uses of oil as an energy
source and as a chemical feedstock.

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 Organic Chemistry
Alkanes
a) Describe an homologous series as a group of compounds with a general
formula, similar chemical properties and showing a gradation in physical
properties as a result of increase in the size and mass of the molecules,
e.g. melting and boiling points; viscosity; flammability.
b) Describe the alkanes as an homologous series of saturated hydrocarbons
with the general formula CnH2n+2.
c) Draw the structures of branched and unbranched alkanes, C1 to C4, and
name the unbranched alkanes, methane to butane.
d) Define isomerism and identify isomers.
e) Describe the properties of alkanes (exemplified by methane) as being
generally unreactive except in terms of burning and substitution by
chlorine.

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 Organic Chemistry
Alkenes
a) Describe the alkenes as an homologous series of unsaturated
hydrocarbons with the general formula CnH2n.
b) Draw the structures of branched and unbranched alkenes, C2 to C4, and
name the unbranched alkenes, ethene to butene.
c) Describe the manufacture of alkenes and hydrogen by cracking
hydrocarbons and recognise that cracking is essential to match the
demand for fractions containing smaller molecules from the refinery
process.
d) Describe the difference between saturated and unsaturated hydrocarbons
from their molecular structures and by using aqueous bromine.
e) Describe the properties of alkenes (exemplified by ethene) in terms of
combustion, polymerisation and the addition reactions with bromine,
steam and hydrogen.
f) State the meaning of polyunsaturated when applied to food products.
g) Describe the manufacture of margarine by the addition of hydrogen to
unsaturated vegetable oils to form a solid product.
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 Organic Chemistry
Alcohols
a) Describe the alcohols as an homologous series containing the –OH group.
b) Draw the structures of alcohols, C1 to C4, and name the unbranched
alcohols, methanol to butanol.
c) Describe the properties of alcohols in terms of combustion and oxidation
to carboxylic acids.
d) Describe the formation of ethanol by the catalysed addition of steam to
ethene and by fermentation of glucose.
e) State some uses of ethanol, e.g. as a solvent; as a fuel; as a constituent of
alcoholic beverages.

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 Organic Chemistry
Carboxylic Acids
a) Describe the carboxylic acids as an homologous series containing the
–CO2H group.
b) Draw the structures of carboxylic acids, methanoic acid to butanoic acid
and name the unbranched acids, methanoic to butanoic acids.
c) Describe the carboxylic acids as weak acids, reacting with carbonates,
bases and some metals.
d) Describe the formation of ethanoic acid by the oxidation of ethanol by
atmospheric oxygen or acidified potassium dichromate(VI).
e) Describe the reaction of a carboxylic acid with an alcohol to form an ester,
e.g. ethyl ethanoate.
f) State some commercial uses of esters, e.g. perfumes; flavourings;
solvents.

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 Organic Chemistry
Macromolecules
a) Describe macromolecules as large molecules built up from small units,
different macromolecules having different units and/or different linkages.
b) Describe the formation of poly(ethene) as an example of addition
polymerisation of ethene as the monomer.
c) State some uses of poly(ethene) as a typical plastic, e.g. plastic bags;
clingfilm.
d) Deduce the structure of the polymer product from a given monomer and
vice versa.
e) Describe nylon, a polyamide, and Terylene, a polyester, as condensation
polymers, the partial structure of nylon being represented as:

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 Organic Chemistry
And the partial structure of Terylene as:

(Details of manufacture and mechanisms of these polymerisations are not

required).
f) State some typical uses of man-made fibres such as nylon and Terylene,
e.g. clothing; curtain materials; fishing line; parachutes; sleeping bags.
g) Describe the pollution problems caused by the disposal of
non-biodegradable plastics.

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Organic Chemistry

What is an
organic
compound?
 Organic Chemistry
Organic Inorganic
Citric Acid – C6H8O7 Aluminium Oxide – Al2O3
Ethanoic Acid – CH3COOH Calcium Carbonate – CaCO3
Ethanol – CH3CH2OH Carbon Dioxide – CO2
Glucose – C6H12O6 Copper(II) Sulfate – CuSO4
Methane – CH4 Sodium Chloride – NaCl
Poly(ethene) – (CH2CH2)n Sulfuric Acid – H2SO4
Propane – C3H8 Water – H2O
 Compare the organic compounds with the
inorganic compounds. What are the differences?
 Organic Chemistry
 An organic compound is a compound that
contains carbon covalently bonded to hydrogen.
 Methane  Carbon dioxide
(formula CH4) (formula CO2)
is organic. is inorganic.
H
H C H O C O
H
Organic Chemistry

What is the nature

of the bonding in
organic
compounds?

 Because only atoms of

non-metallic elements are
present, the bonding in organic
compounds is covalent.
Organic Chemistry
Bonding in Organic Compounds
Ethane – C2H6
Organic Chemistry
Bonding in Organic Compounds
Ethene – C2H4
Organic Chemistry
Bonding in Organic Compounds
Ethyne – C2H2
Organic Chemistry
Bonding in Organic Compounds
Ethanol – CH3CH2OH
Organic Chemistry
Bonding in Organic Compounds
Ethanoic Acid – CH3COOH
Organic Chemistry

What properties
of carbon make it
such an important
element?
 Organic Chemistry
 Compare the bonding in the organic compounds with the bonding in the
inorganic elements and compounds. What similarities and differences do
you notice?
H
O
H H H S S S H H
H C H S S
C C H Si Si Si H S H C C O
H H H S S H H H
C C
H C H
N O H O
H C N O
O S O H H H H
C H
H H O H
H
P
H H H H H H H H
H C C C C C C C C H P P
H H H H H H H H
P
 Organic Chemistry
 Compare the bond strengths between i) carbon atoms, ii) carbon atoms
and other elements iii) other elements (excluding carbon). What similarities
and differences do you notice?

H H H
Bond Bond Bond
kJ/mol kJ/mol kJ/mol
C–C 348 C–H 412 C=C 612
Si – Si 176 Si – H 318 CC 837
N–N 163 N–H 388 C–N 305
O–O 146 O–H 463 C=N 613
P–P 172 P–H 322 CN 890
S–S 264 S–H 338 C–O 360
Cl – Cl 242 Cl – H 431 C – Cl 338
 Organic Chemistry
The Special Properties of carbon

 Carbon is in Group IV of the Periodic Table. It

has four electrons in its valence shell and
therefore makes four covalent bonds with atoms
of other non-metallic elements.
Carbon is described as being tetravalent.
 The covalent bond between two carbon atoms
is very strong. This allows carbon atoms to join
together in large numbers to form long-chains
and complex rings.
Carbon is said to catenate.
 Organic Chemistry
The Special Properties of carbon

 The complex structure of the antibiotic penicillin.

Organic Chemistry

What is a
homologous
series?
 Organic Chemistry
Homologous Series
 A homologous series of organic compounds is a group
of molecules that possess the same functional group,
share the same general formula and have similar names.
 A functional group is a group of atoms that are bonded
together in a way that is unique to that particular
homologous series. The functional group is responsible
for a compound’s characteristic chemical properties.
 Because they all possess the same functional group,
members of the same homologous series will all react in
a similar way to each other.
 Organic Chemistry
Homologous Series – Alkanes

H H H H H
H C C H H C C C H
H H H H H
 Ethane  Propane
 Organic Chemistry
Homologous Series – Alkanes

Functional Group C C

General Formula CnH2n+2

Name -ane
 Organic Chemistry
Homologous Series – Alkenes

 Ethene  Propene
 Organic Chemistry
Homologous Series – Alkenes

Functional Group C C

General Formula CnH2n

Name -ene
 Organic Chemistry
Homologous Series – Alcohols

 Ethanol  Propan-1-ol
 Organic Chemistry
Homologous Series – Alcohols

Functional Group
hydroxyl
C O H

General Formula CnH2n+1OH

Name -ol
 Organic Chemistry
Homologous Series – Halogenoalkanes

 Bromoethane  1-Chloropropane
 Organic Chemistry
Homologous Series – Halogenoalkanes

Functional Group C Halogen

General Formula CnH2n+1Hal

Bromo-
Name
Chloro-
 Organic Chemistry
Homologous Series – Carboxylic Acids

 Ethanoic Acid  Propanoic Acid

 Organic Chemistry
Homologous Series – Carboxylic Acids

O
Functional Group
C
carboxyl
O H
General Formula CnH2nO2
Name -oic acid
 Organic Chemistry
Homologous Series – Esters

 Ethyl Ethanoate  Methyl Propanoate

 Organic Chemistry
Homologous Series – Esters

O
C
Functional Group
O C

General Formula CnH2nO2

Name -yl -anoate
Organic Chemistry

What are the

names and
formulae of the first
10 straight chain
alkanes?
 Organic Chemistry
Naming Straight Chain Alkanes
 The alkanes are saturated hydrocarbons with the
general formula CnH2n+2.
 Saturated means that the bonds between the carbon
atoms are all single covalent bonds, there are no double
or triple covalent bonds.
 Hydrocarbon means that the alkanes are composed
only of the two elements hydrogen and carbon.
 General formula of CnH2n+2. For example, if n = 2, then
(2  2) + 2 = 6, so the formula of the alkane that contains
two carbon atoms will be C2H6.
Organic Chemistry
Naming Straight Chain Alkanes

Methane
H
H C H
H

CH4
Melting Point = −182.5C
Boiling Point = −161.6C
 Organic Chemistry
Naming Straight Chain Alkanes

Methane
H
Prefix: Suffix:
Denotes the H C H Denotes the
number of homologous series
carbon atoms H that the compound
in the molecule. belongs to.
CH4
Melting Point = −182.5C
Boiling Point = −161.6C
Organic Chemistry
Naming Straight Chain Alkanes

Ethane
H H
H C C H
H H

C2H6
Melting Point = −181.8C
Boiling Point = −89.0C
Organic Chemistry
Naming Straight Chain Alkanes

Propane
H H H
H C C C H
H H H

C3H8
Melting Point = −187.7C
Boiling Point = −42.1C
Organic Chemistry
Naming Straight Chain Alkanes

Butane
H H H H
H C C C C H
H H H H

C4H10
Melting Point = −138.4C
Boiling Point = −0.5C
Organic Chemistry
Naming Straight Chain Alkanes

Pentane
H H H H H
H C C C C C H
H H H H H

C5H12
Melting Point = −129.8C
Boiling Point = 36.1C
Organic Chemistry
Naming Straight Chain Alkanes

Hexane
H H H H H H
H C C C C C C H
H H H H H H

C6H14
Melting Point = −95.3C
Boiling Point = 68.7C
 Organic Chemistry
Naming Straight Chain Alkanes

Heptane
H H H H H H H
H C C C C C C C H
H H H H H H H

C7H16
Melting Point = −90.6C
Boiling Point = 98.4C
 Organic Chemistry
Naming Straight Chain Alkanes

Octane
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

C8H18
Melting Point = −57.0C
Boiling Point = 125.5C
 Organic Chemistry
Naming Straight Chain Alkanes

Nonane
H H H H H H H H H
H C C C C C C C C C H
H H H H H H H H H

C9H20
Melting Point = −53.0C
Boiling Point = 151.0C
 Organic Chemistry
Naming Straight Chain Alkanes

Decane
H H H H H H H H H H
H C C C C C C C C C C H
H H H H H H H H H H

C10H22
Melting Point = −27.9C
Boiling Point = 174.1C
 Organic Chemistry
Naming Branched Chain Alkanes

2-Methylpentane
H H H
Methyl group H C H H H Indicates the
(–CH3) bonded longest carbon
to carbon 1 2 3 4 5 chain. Five
No. 2 of the H C C C C C H carbon atoms
longest = pentane.
carbon chain. H H H H H
2-methylpentane
 Organic Chemistry
Naming Branched Chain Alkanes

2,3-Dimethylbutane
H H H
Two methyl H C H H Indicates the
groups (–CH3), longest carbon
one bonded 1 2 3 4 chain. Four
to carbon
H C C C C H carbon atoms
No. 2, and one = butane.
bonded to H H C H
carbon No. 3 H H H
of the longest
carbon chain.
2,3-dimethylbutane
 Organic Chemistry
Naming Cyclic Alkanes

Cyclobutane
H H
The prefix cyclo– H C C H Indicates the
indicates that the longest carbon
carbon atoms chain. Four
are arranged in H C C H carbon atoms
a ring. = butane.
H H
cyclobutane
 Organic Chemistry
Naming Straight Chain Alkanes
m.p. / C b.p. / C
Relative Molecular
Name Formula Mass

Methane CH4 16 –182.5 –161.6

Ethane C2H6 30 –181.8 –89.0
Propane C3H8 44 –187.7 –42.1
Butane C4H10 58 –138.4 –0.5
Pentane C5H12 72 –129.8 36.1
Hexane C6H14 86 –95.3 68.7
Heptane C7H16 100 –90.6 98.4
Octane C8H18 114 –57.0 125.5
Nonane C9H20 128 –53.0 151.0
Decane C10H22 142 –27.9 174.1
 Organic Chemistry
Naming Straight Chain Alkanes
 The melting points and boiling points of the alkanes
increases as the length of the carbon chain increases.
 The melting points and boiling points of the alkanes
increases as relative molecular mass increases.
 A complex mixture of alkanes can be separated by
fractional distillation.
 On an industrial scale, the complex mixture of alkanes
in crude oil is separated by fractional distillation in an
oil refinery.
Organic Chemistry
Naming Straight Chain Alkanes

 The melting points and

boiling points of the alkanes
increases as relative
molecular mass increases.
This is because the surface
area of the molecules
increases, hence
intermolecular forces of
attraction (Van der Waals
forces) become stronger.
More energy is required to
weaken the force of
attraction between the
molecules.
Organic Chemistry
Naming Straight Chain Alkanes

 The melting points and

boiling points of the alkanes
increases as relative
molecular mass increases.
This is because the surface
area of the molecules
increases, hence
intermolecular forces of
attraction (Van der Waals
forces) become stronger.
More energy is required to
weaken the force of
attraction between the
molecules.
Organic Chemistry
Naming Straight Chain Alkanes
 As relative molecular mass
increases, the liquid alkanes
become more viscous. This
is because the length of the
hydrocarbon chain increases
and hence their surface area
increases. Consequently,
intermolecular forces of
attraction (Van der Waals
forces) become stronger and
the molecules are unable to
slip and slide over each
other as easily.
Organic Chemistry
Naming Straight Chain Alkanes
 As relative molecular mass
increases, the alkanes
become less flammable. As
the surface area of the
molecules increases, the
intermolecular forces of
attraction (Van der Waals
forces) also increase and the
alkanes become less
volatile. Alkanes burn when
gaseous. The less likely an
alkane is to be gaseous, the
less likely it is to ignite
and burn.
 Organic Chemistry
Naming Straight Chain Alkanes
H H H H H
 Pentane and 2,2-dimethylpropane are
H C C C C C H isomers, i.e. they share the same
H H H H H molecular formula (C5H12), but have
pentane different structural formulae. Pentane boils
at 31.6 C, while 2,2-dimethylpropane boils
at 9.50 C. The difference in boiling points
H H H
H C H
is due to the difference in their surface
areas. The larger surface area of pentane
H C C C H
results in stronger intermolecular forces of
H C H
H H H
attraction (Van der Waals forces) between
the molecules, which require more energy
2,2-dimethylpropane to overcome, hence increasing the
(or just dimethylpropane) boiling point.
Organic Chemistry

How do I name the

alkenes,
halogenoalkanes,
alcohols and
carboxylic acids?
 Organic Chemistry
Naming Alkenes
 The alkenes are unsaturated hydrocarbons with the
general formula CnH2n.
 Unsaturated means that the molecule contains at least
one carbon-to-carbon double covalent bond.
 Hydrocarbon means that the alkenes are composed
only of the two elements hydrogen and carbon.
 General formula of CnH2n. For example, if n = 3, then
2  3 = 6, so the formula of the alkene that contains three
carbon atoms will be C3H6.
Organic Chemistry
Naming Alkenes

Ethene
H H
C C
H H

C2H4
 Organic Chemistry
Naming Alkenes

Ethene
H H
Prefix: Suffix:
Denotes the C C Denotes the
number of homologous series
carbon atoms
H H that the compound
in the molecule. belongs to.
C2H4
Organic Chemistry
Naming Alkenes

Propene
H H H
C C C H
H H

C3 H6
Organic Chemistry
Naming Alkenes

But-1-ene
H H H H
1 2 3 4
C C C C H
H H H

C4H8
Organic Chemistry
Naming Alkenes

But-1-ene
H H H H Number:
1 2 3 4 Indicates the
C C C C H location of the
C=C bond
H H H within the
molecule.

C4H8
Organic Chemistry
Naming Alkenes

But-2-ene
H H H H
1 2 3 4
H C C C C H
H H

C4H8
Organic Chemistry
Naming Alkenes

But-2-ene
H H H H Number:
1 2 3 4 Indicates the
H C C C C H location of the
C=C bond
H H within the
molecule.

C4H8
 Organic Chemistry
Naming Halogenoalkanes
 The halogenoalkanes are alkanes in which at least one
of the hydrogen atoms has been substituted by a
halogen (Group VII element).

 The general formula of the halogenoalkanes is

CnH2n+1Hal, where Hal is the symbol of a Group VII
element (i.e. F, Cl, Br, I). For example, if n = 4, then
(2  4) + 1 = 9, so the formula of the halogenoalkane that
contains four carbon atoms and chlorine will be C4H9Cl.
Organic Chemistry
Naming Halogenoalkanes

Chloromethane
H
H C Cl
H

CH3Cl
 Organic Chemistry
Naming Halogenoalkanes

Chloromethane
H
Prefix: Suffix:
Indicates the H C Cl Denotes the
Group VII number of
element that H carbon atoms
is present in in the molecule.
the compound,
F = fluoro-
CH3Cl
Cl = chloro-
Br = bromo-
I = Iodo-
Organic Chemistry
Naming Halogenoalkanes

Bromoethane
H H
H C C Br
H H

C2H5Br
Organic Chemistry
Naming Halogenoalkanes

1-Chloropropane
H H H
3 2 1
H C C C Cl
H H H

C3H7Cl
 Organic Chemistry
Naming Halogenoalkanes

1-Chloropropane
H H H
Number: 3 2 1
Indicates the
H C C C Cl
location of the
chlorine atom
H H H
within the
molecule. C3H7Cl
Organic Chemistry
Naming Halogenoalkanes

2-Chloropropane
H Cl H
1 2 3
H C C C H
H H H

C3H7Cl
 Organic Chemistry
Naming Halogenoalkanes

2-Chloropropane
H Cl H
Number: 1 2 3
Indicates the
H C C C H
location of the
chlorine atom
H H H
within the
molecule. C3H7Cl
 Organic Chemistry
Naming Alcohols
 The alcohols are alkanes in which at least one of the
hydrogen atoms has been substituted by a hydroxyl
group, O–H.
 The general formula of the alcohols is CnH2n+1OH. For
example, if n = 5, then (2  5) + 1 = 11, so the formula of
the alcohol that contains five carbon atoms will be
C5H11OH.
 Organic Chemistry
Naming Alcohols

Methanol
H
Prefix: Suffix:
Denotes the H C O Denotes the
number of H homologous series
carbon atoms H that the compound
in the molecule. belongs to.
CH3OH
Melting Point = –97.6 C
Boiling Point = 64.7 C
Organic Chemistry
Naming Alcohols

Ethanol
H H
H C C O
H H H

C2H5OH
Melting Point = –114 C
Boiling Point = 78.2 C
Organic Chemistry
Naming Alcohols

Propan-1-ol
H H H Number:
3 2 1 Indicates the
H C C C O location of the
O–H group
H H H H within the
molecule.

C3H7OH
Melting Point = –126 C
Boiling Point = 97.5 C
Organic Chemistry
Naming Alcohols

Propan-1-ol
H H H
3 2 1
H C C C O
H H H H

C3H7OH
Organic Chemistry
Naming Alcohols

Propan-1-ol
H H H Number:
3 2 1 Indicates the
H C C C O location of the
O–H group
H H H H within the
molecule.

C3H7OH
Organic Chemistry
Naming Alcohols

Propan-2-ol
H
H O H
1 2 3
H C C C H
H H H

C3H7OH
Organic Chemistry
Naming Alcohols

Propan-2-ol
H Number:
Indicates the
H O H location of the
1 2 3 O–H group
H C C C H within the
molecule.
H H H

C3H7OH
 Organic Chemistry
Naming Carboxylic Acids
 The general formula of the carboxylic acids is CnH2nO2.
For example, if n = 6, then 2  6 = 12, so the formula of
the carboxylic acid that contains six carbon atoms will be
C6H12O2.
Note: The carboxylic acid functional group is COOH
(carboxyl). This is normally written separately in the
formula, so C6H12O2 is re-written as C5H11COOH.
 Remember, the carboxylic acids are weak acids, i.e.
they only partially ionise when dissolved in water.
CH3COOH Ý CH3COO– + H+
 Organic Chemistry
Naming Carboxylic Acids

Methanoic Acid
O
H C
O H

CHOOH
By default, the C of COOH is always No. 1.
 Organic Chemistry
Naming Carboxylic Acids

Methanoic Acid
O
Prefix: Suffix:
Denotes the H C Denotes the
number of homologous series
carbon atoms O H that the compound
in the molecule. belongs to.
CHOOH
By default, the C of COOH is always No. 1.
 Organic Chemistry
Naming Carboxylic Acids

Ethanoic Acid
H O
H C C
H O H

CH3COOH
By default, the C of COOH is always No. 1.
 Organic Chemistry
Naming Carboxylic Acids

Propanoic Acid
H H O
H C C C
H H O H

C2H5COOH
By default, the C of COOH is always No. 1.
 Organic Chemistry
Naming Carboxylic Acids

Butanoic Acid
H H H O
H C C C C
H H H O H

C3H7COOH
By default, the C of COOH is always No. 1.
 Organic Chemistry
Hierarchy of Functional Groups in Naming Compounds
O
 Higher Priority C  Carboxylic Acid
O H

C O H  Alcohol

C C  Alkene

 Lower Priority C Halogen  Halogenoalkane

 Higher priority groups have lower numbers

assigned to them when naming.
 Organic Chemistry
Hierarchy of Functional Groups in Naming Compounds

CHCl2–CH2–CH2–CH2OH

4,4-dichlorobutan-1-ol not 1,1-dichlorobutan-4-ol

 The hydroxyl group of the alcohol is given the priority
of having the lower number.

CHCl2–CH2–CH=CH2

4,4-dichlorobut-1-ene not 1,1-dichlorobut-3-ene

 The carbon-to-carbon double covalent bond of the
alkene is given the priority of having the lower number.
 Organic Chemistry
Hierarchy of Functional Groups in Naming Compounds

CH2Cl–CHCl–CH2–COOH

3,4-dichlorobutanoic acid not 1,2-dichlorobutan-4-oic acid

 The carbon of the carboxylic acid group (carboxyl
group) is given the priority of having the lower number.

CH2=CH–CH2–CH2–COOH

pent-4-enoic acid not pent-1-en-5-oic acid

 The carbon of the carboxylic acid group (carboxyl
group) is given the priority of having the lower number.
Organic Chemistry

What is the origin

of the organic
compounds that
are used by
chemists?
Organic Chemistry
 Organic Chemistry
Origin of Crude Oil (Petroleum)
 Millions of years ago, tiny sea creatures and plants sank
to the seabed when they died. The dead sea creatures and
plants were slowly covered by mud and sand.
 Heat from the Earth and pressure from the mud and sand
acted on these organisms over millions of years, eventually
producing crude oil (petroleum) and natural gas.
 Petroleum and natural gas are often found in underground
deposits hundreds, or thousands, of metres below the
surface of the Earth. Deep wells have to be drilled to extract
them.
Organic Chemistry
Origin of Crude Oil (Petroleum)
 Organic Chemistry
Origin of Crude Oil (Petroleum)
 Crude oil (petroleum) is a very complex mixture of
organic compounds.
 Crude oil is a dark brown, toxic, foul smelling and
viscous liquid.
 Crude oil can be separated into useful fractions by
fractional distillation.
 Each crude oil fraction is a mixture of hydrocarbons
that boils over a certain temperature.
 Lighter fractions consist of smaller hydrocarbons.
 Heavier fractions consist of larger hydrocarbons.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 Diagram to illustrate some uses of the different

fractions that are separated from crude oil.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 Petrol – C5H12 to C10H22 – is an important fraction that

is separated from crude oil by fractional distillation.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
Petroleum C1 – C4
Gas b.p. = < 40 C

C5 – C10
Petrol b.p. = 40 – 75 C

C7 – C14
Naphtha b.p. = 90 – 150 C

Paraffin C9 – C16
(Kerosene) b.p. = 150 – 240 C

Diesel C15 – C25

Oil b.p. = 220 – 250 C
Crude
Oil Lubricating C20 – C35
Oil b.p. = 300 – 350 C

> C70
Bitumen b.p. = > 350 C
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
Name of Number of Boiling Point Use of
Fraction Carbon Atoms / C Fraction
Fuel for cooking and
Petroleum Gas C1 – C4 < 40 heating.

Petrol C5 – C10 40 – 75 Fuel for motorcars.

Feedstock for the

Naphtha C7 – C14 90 – 150 chemical industry.
Paraffin Fuel for aircraft,
(Kerosene)
C9 – C16 150 – 240 cooking and heating.
Fuel for buses,
Diesel Oil C15 – C25 220 – 250 lorries and trains.
For lubricating
Lubricating Oil C20 – C35 300 – 350 machines.
For making road
Bitumen > C70 > 350 surfaces and roofing.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
The catalytic cracking of long-chain alkanes produces short-
chain alkanes and alkenes as reaction products. Short-chain
alkanes tend to be more useful than long-chain alkanes, and
alkenes can be used in organic synthesis.
High
H H H H H H H H Temperature / H H H H H H H H
Catalyst
H C C C C C C C C H H C C C C C C H + C C
Al2O3 H H
H H H H H H H H H H H H H H
Octane Hexane Ethene
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 An experiment to crack a long-chain hydrocarbon in the lab.

Note that the insoluble ethene gas is collected by the
downward displacement of water.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 Accidents during the transport of crude oil can

lead to environmental disasters.
 The non-polar hydrocarbon molecules in crude
oil are immiscible with the polar solvent water.
 Crude oil is less dense than water.
 The crude oil coats plants and animals with a
thick, viscous layer of toxic chemicals which will
eventually kill them if not removed.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 Crude oil, coal and natural gas are fossil fuels.

They are non-renewable sources of energy, and
will eventually run out.
 It is important to develop alternative sources of
clean and renewable energy.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 The combustion of fossil fuels produce

pollutants such as:
 Carbon dioxide  causes global warming.
 Carbon monoxide  toxic.
 Oxides of nitrogen  irritant, causes acid rain.
 Sulfur dioxide  irritant, causes acid rain.
 Unburned hydrocarbons  cause cancer.
 Organic Chemistry
Fractional Distillation of Crude Oil (Petroleum)

 Pollutants can be removed from car exhaust fumes

using catalytic converters.
Organic Chemistry

What are
isomers?
 Organic Chemistry
Isomers

 Isomers are compounds that share the same

molecular formula, but have different structural
formulas (arrangement of atoms).
 Isomers may or may not belong to the same
homologous series.
 Isomers have different names.
Organic Chemistry
There are Two Isomers of C4H10:
 Organic Chemistry
There are Two Isomers of C4H10:
H H H
H H H H H C H
H C C C C H H C C C H
H H H H H H H
butane 2-methylpropane
(or just methylpropane)
 Organic Chemistry
There are Two Isomers of C4H10:
H H H
H H H H H C H
H C C C C H H C C C H
H H H H H H H
butane 2-methylpropane
(or just methylpropane)
H H H H H H
H H H C H
C H H H C C C H
H C C H
H C C C H H H C
H C H H H
H H H H H H
This is butane not This is butane not
1-methylpropane This is butane not 1-methylpropane
1,2-dimethylethane
Organic Chemistry
What are the Isomers of C4H9Br?
 Organic Chemistry
What are the Isomers of C4H9Br?

H H H H H Br H H
Br C C C C H H C C C C H
H H H H H H H H
1-bromobutane 2-bromobutane

H H H H H H
H C H H C H
Br C C C H H C C C H
H H H H Br H
1-bromo-2-methylpropane 2-bromo-2-methylpropane
(or just 1-bromomethylpropane) (or just 2-bromomethylpropane)
Organic Chemistry
What are the Isomers of C5H12?
 Organic Chemistry
What are the Isomers of C5H12?

H H H
H H H H C H
H H H H H H C H H
H C C C H
H C C C C C H H C C C C H
H C H
H H H H H H H H H H H H
pentane 2-methylbutane
(or just methylbutane) 2,2-dimethylpropane
(or just dimethylpropane)
Organic Chemistry
What are the Isomers of C6H14?
 Organic Chemistry
What are the Isomers of C6H14?

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

2,2-dimethylbutane 2,3-dimethylbutane
Organic Chemistry
What are the Isomers of C4H8?
 Organic Chemistry
What are the Isomers of C4H8?
Geometric Isomers!
H H
H H H H
H H H H H H H H H C H
H C C H
C C C C H H C C C C H C C
C C
H H H H H H C H
H H
H H
but-1-ene but-2-ene cis-but-2-ene
trans-but-2-ene
H
H H H H H H H
H C H C
H C C H H
C C C H C
H C C H
H H H C C H
H H
H H
2-methylprop-1-ene cyclobutane
(or just methylpropene) methylcyclopropane
Organic Chemistry

How do I calculate
the formula of an
organic compound
from its percentage
composition?
 Organic Chemistry
Calculation of Formula from Percentage Composition
 Calculate the empirical formula of the hydrocarbon
that has the following percentage composition:
C = 85.7% H = 14.3 %
 Given that the relative molecular mass of the
hydrocarbon is 42.0, calculate the molecular
formula of the hydrocarbon.
 This hydrocarbon has two isomers. Give the
structural formulae and names of the two isomers.
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 1: Divide each element’s percentage by

the element’s relative atomic mass.
 For carbon: 85.7  12.0 = 7.14
 For hydrogen: 14.3  1.0 = 14.3
How does this calculation work? Imagine that you had 100 g of the hydrocarbon. 85.7 g of the compound would be carbon,
and 14.3 g would be hydrogen. Remember, mass in grams divided by relative atomic mass gives number of moles as
the answer. So, 85.7  12.0 = 7.14 moles of carbon and 14.3  1.0 = 14.3 moles of hydrogen. The simple mole ratio of
elements in a compound gives us the empirical formula of the compound.
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 2: Divide each one of the answers

by the smallest answer.
 For carbon: 7.14  7.14 = 1.00
 For hydrogen: 14.3  7.14 = 2.00
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 3: This gives the compound’s empirical

formula which is the most simple ratio of
elements in the compound.

CH2
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 4: Calculate the relative molecular mass

of the compound’s empirical formula.
= C + (2  H)
= 12.0 + (2  1.0)

= 14.0
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 5: Divide the relative molecular mass of the

compound’s molecular formula by the relative
molecular mass of the compound’s
empirical formula.
= 42.0  14.0

= 3.00
 Organic Chemistry
Calculation of Formula from Percentage Composition

Step 6: Multiply the empirical formula by the

answer to Step 5 to determine the compound’s
molecular formula.
= CH2  3.00

C3H6
 Organic Chemistry
Calculation of Formula from Percentage Composition

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

Propene
Cyclopropane
Organic Chemistry

How are the

reactions of
organic
compounds
classified?
 Organic Chemistry
Classification of Organic Reactions

Organic reactions can be classified

into (at least) three main types:
 Addition.
 Elimination.
 Substitution.
 Organic Chemistry
Classification of Organic Reactions

H H Br Br
C C + Br2 H C C H
H H H H
Ethene 1,2-Dibromoethane

Unsaturated Saturated
 Organic Chemistry
Classification of Organic Reactions

H H Br Br
C C + Br2 H C C H
H H H H
Ethene 1,2-Dibromoethane

Unsaturated Saturated
 Organic Chemistry
Classification of Organic Reactions

H H H H
H C C Br + KOH(ethanol) C C + KBr + H2O
H H H H
Bromoethane Ethene

Saturated Unsaturated
 Organic Chemistry
Classification of Organic Reactions

H H H H
H C C Br + KOH(ethanol) C C + KBr + H2O
H H H H
Bromoethane Ethene

Saturated Unsaturated
 Organic Chemistry
Classification of Organic Reactions

Substitute

H H H H
H C C Br + KOH(aqueous) H C C OH + KBr
H H H H
Bromoethane Ethanol
 Organic Chemistry
Classification of Organic Reactions

Substitute

H H H H
H C C Br + KOH(aqueous) H C C OH + KBr
H H H H
Bromoethane Ethanol
 Organic Chemistry
Classification of Organic Reactions

H H H H Br Br
H C C C + Br2 H C C C H
H H H H H
Propene 1,2-Dibromopropane
 Organic Chemistry
Classification of Organic Reactions

H H H H Br Br
H C C C + Br2 H C C C H
H H H H H
Propene 1,2-Dibromopropane
 Organic Chemistry
Classification of Organic Reactions

H H H H
H H H
C C H
H C C Br H C C
+ KOH(ethanol) + KBr + H2O
H C C H H C C
C C H
H H H
H H H H
Bromo- Cyclohexene
cyclohexane
 Organic Chemistry
Classification of Organic Reactions

H H H H
H H H
C C H
H C C Br H C C
+ KOH(ethanol) + KBr + H2O
H C C H H C C
C C H
H H H
H H H H
Bromo- Cyclohexene
cyclohexane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H
H C C C C + H2 H C C C C H
H H H H H H H
But-1-ene Butane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H
H C C C C + H2 H C C C C H
H H H H H H H
But-1-ene Butane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H H
H C C C C Br + NH3 H C C C C N + HBr
H H H H H H H H H
1-Bromobutane Butyl-1-amine
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H H
H C C C C Br + NH3 H C C C C N + HBr
H H H H H H H H H
1-Bromobutane Butyl-1-amine
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C C C Cl + KOH(ethanol) H C C C + KCl + H2O
H H H H H
1-Chloropropane Propene
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C C C Cl + KOH(ethanol) H C C C + KCl + H2O
H H H H H
1-Chloropropane Propene
 Organic Chemistry
Classification of Organic Reactions

H H H H H H Br H
H C C C C H + HBr H C C C C H
H H H H H H
But-2-ene 2-Bromobutane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H Br H
H C C C C H + HBr H C C C C H
H H H H H H
But-2-ene 2-Bromobutane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C C C Cl + H2O H C C C OH + HCl
H H H H H H
1-Chloropropane Propan-1-ol
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C C C Cl + H2O H C C C OH + HCl
H H H H H H
1-Chloropropane Propan-1-ol
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H
H C C C C OH H C C C C + H2O
H H H H H H H
Butan-1-ol But-1-ene
 Organic Chemistry
Classification of Organic Reactions

H H H H H H H H
H C C C C OH H C C C C + H2O
H H H H H H H
Butan-1-ol But-1-ene
 Organic Chemistry
Classification of Organic Reactions

H H H H
H C C Br + KC N H C C C N + KBr
H H H H
Bromoethane Propanenitrile
 Organic Chemistry
Classification of Organic Reactions

H H H H
H C C Br + KC N H C C C N + KBr
H H H H
Bromoethane Propanenitrile
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C H H C H
H C C C Br + KOH(ethanol) H C C C + KBr + H2O
H H H H H
1-Bromo-2- 2-Methylpropene
methylpropane or Methylpropene
or
1-Bromo-
methylpropane
 Organic Chemistry
Classification of Organic Reactions

H H H H H H
H C H H C H
H C C C Br + KOH(ethanol) H C C C + KBr + H2O
H H H H H
1-Bromo-2- 2-Methylpropene
methylpropane or Methylpropene
or
1-Bromo-
methylpropane
 Organic Chemistry
Classification of Organic Reactions

H H H
H C
H C H H H C H
C C C C
+ H C Br + HBr
C C C C
H C H H H C H
H H
Benzene Methylbenzene
 Organic Chemistry
Classification of Organic Reactions

H H H
H C
H C H H H C H
C C C C
+ H C Br + HBr
C C C C
H C H H H C H
H H
Benzene Methylbenzene
 Organic Chemistry
Classification of Organic Reactions

H H H H
H H H
C H C
H C C H C C OH
+ H2O
H C C H C C H
C H C
H H H
H H H H
Cyclohexene Cyclohexanol
 Organic Chemistry
Classification of Organic Reactions

H H H H
H H H
C H C
H C C H C C OH
+ H2O
H C C H C C H
C H C
H H H
H H H H
Cyclohexene Cyclohexanol
Organic Chemistry
Presentation on
Organic Chemistry
By Dr. Chris Slatter
christopher_john_slatter@nygh.edu.sg

Nanyang Girls’ High School

2 Linden Drive
Singapore
288683

14th February 2016