organic chemistry introduction · 2017. 8. 3. · organic chemistry learning outcomes: candidates...
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Organic
Chemistry
Introduction
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What do I
need to know
about organic
chemistry?
Organic Chemistry
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Organic ChemistryOverview
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.
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
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Organic ChemistryLearning 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.
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
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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.
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
Organic Chemistry
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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.
Organic Chemistry
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
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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.
Organic Chemistry
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
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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.
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
Organic Chemistry
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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.
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
Organic Chemistry
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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:
Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
Organic Chemistry
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Singapore Examinations and Assessment
Board University of Cambridge International Examinations
Ministry of Education Singapore
Organic ChemistryAnd 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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What is an
organic
compound?
Organic Chemistry
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Organic Chemistry
Organic Inorganic
Glucose – C6H12O6
Ethanoic Acid – CH3COOH
Ethanol – CH3CH2OH
Methane – CH4
Poly(ethene) – (CH2CH2)n
Sodium Chloride – NaCl
Carbon Dioxide – CO2
Water – H2O
Calcium Carbonate – CaCO3
Sulfuric Acid – H2SO4
Aluminium Oxide – Al2O3
Copper(II) Sulfate – CuSO4
Propane – C3H8
Citric Acid – C6H8O7
Compare the organic compounds with the
inorganic compounds. What are the differences?
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Organic Chemistry An organic compound is a compound that
contains carbon covalently bonded to hydrogen.
Methane
(formula CH4)
is organic.
H
CH
H
H
Carbon dioxide
(formula CO2)
is inorganic.
O C O
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What is the nature
of the bonding in
organic
compounds?
Organic Chemistry
Because only atoms of
non-metallic elements are
present, the bonding in organic
compounds is covalent.
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Organic ChemistryBonding in Organic Compounds
Ethane – C2H6
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Organic ChemistryBonding in Organic Compounds
Ethene – C2H4
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Organic ChemistryBonding in Organic Compounds
Ethyne – C2H2
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Organic ChemistryBonding in Organic Compounds
Ethanol – CH3CH2OH
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Organic ChemistryBonding in Organic Compounds
Ethanoic Acid – CH3COOH
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What properties
of carbon make it
such an important
element?
Organic Chemistry
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Organic Chemistry
P P
P
P
H Si
H
H
Si
H
H
Si
H
H
H
O
SO O
O H
H
SS
S
SS
SS S
H HN
H H HO
H
CH
H
C
H
H
O
H
C
CC
C
CC
O
N
H
H C
H H
HH
C
O
H HH
Compare the bonding in the organic compounds with the bonding in the
inorganic elements and compounds. What similarities and differences do
you notice?
H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
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Organic Chemistry
BondH
kJ/molBond
H
kJ/molBond
H
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
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?
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Organic ChemistryThe 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.
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Organic Chemistry
The complex structure of the antibiotic penicillin.
The Special Properties of carbon
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What is a
homologous
series?
Organic Chemistry
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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 ChemistryHomologous Series
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Organic ChemistryHomologous Series – Alkanes
Propane
H C
H
H
C
H
H
C
H
H
HH C
H
H
C
H
H
H
Ethane
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Organic ChemistryHomologous Series – Alkanes
Functional Group
General Formula CnH2n+2
Name -ane
C C
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Ethene Propene
Organic ChemistryHomologous Series – Alkenes
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Organic ChemistryHomologous Series – Alkenes
Functional Group
General Formula CnH2n
Name -ene
C C
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Ethanol Propan-1-ol
Organic ChemistryHomologous Series – Alcohols
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Organic ChemistryHomologous Series – Alcohols
Functional Group
hydroxyl
General Formula CnH2n+1OH
Name -ol
C O H
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Bromoethane 1-Chloropropane
Organic ChemistryHomologous Series – Halogenoalkanes
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Organic ChemistryHomologous Series – Halogenoalkanes
Functional Group
General Formula CnH2n+1Hal
NameBromo-
Chloro-
C Halogen
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Ethanoic Acid Propanoic Acid
Organic ChemistryHomologous Series – Carboxylic Acids
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Organic ChemistryHomologous Series – Carboxylic Acids
Functional Group
carboxyl
General Formula CnH2nO2
Name -oic acid
C
O H
O
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Ethyl Ethanoate
Organic ChemistryHomologous Series – Esters
Methyl Propanoate
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Organic ChemistryHomologous Series – Esters
Functional Group
General Formula CnH2nO2
Name -yl -anoate
O C
O
C
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What are the
names and
formulae of the first
10 straight chain
alkanes?
Organic Chemistry
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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 ChemistryNaming Straight Chain Alkanes
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H C
H
H
H
CH4Melting Point = −182.5C
Boiling Point = −161.6C
Methane
Organic ChemistryNaming Straight Chain Alkanes
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H C
H
H
H
CH4Melting Point = −182.5C
Boiling Point = −161.6C
Methane
Prefix:
Denotes the
number of
carbon atoms
in the molecule.
Suffix:
Denotes the
homologous series
that the compound
belongs to.
Organic ChemistryNaming Straight Chain Alkanes
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H C
H
H
C
H
H
H
C2H6Melting Point = −181.8C
Boiling Point = −89.0C
Organic ChemistryNaming Straight Chain Alkanes
Ethane
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H C
H
H
C
H
H
C
H
H
H
C3H8Melting Point = −187.7C
Boiling Point = −42.1C
Organic ChemistryNaming Straight Chain Alkanes
Propane
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H C
H
H
C
H
H
C
H
H
C
H
H
H
C4H10Melting Point = −138.4C
Boiling Point = −0.5C
Organic ChemistryNaming Straight Chain Alkanes
Butane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C5H12Melting Point = −129.8C
Boiling Point = 36.1C
Organic ChemistryNaming Straight Chain Alkanes
Pentane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C6H14Melting Point = −95.3C
Boiling Point = 68.7C
Organic ChemistryNaming Straight Chain Alkanes
Hexane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C7H16Melting Point = −90.6C
Boiling Point = 98.4C
Organic ChemistryNaming Straight Chain Alkanes
Heptane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C8H18Melting Point = −57.0C
Boiling Point = 125.5C
Organic ChemistryNaming Straight Chain Alkanes
Octane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C9H20Melting Point = −53.0C
Boiling Point = 151.0C
Organic ChemistryNaming Straight Chain Alkanes
Nonane
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
C10H22Melting Point = −27.9C
Boiling Point = 174.1C
Organic ChemistryNaming Straight Chain Alkanes
Decane
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Organic ChemistryNaming Branched Chain Alkanes
H C
H
H
C
C
H
C
H
H
C
H HH
H
H
C
H
H
H
2-methylpentane
2-Methylpentane
Methyl group
(–CH3) bonded
to carbon
No. 2 of the
longest
carbon chain.
Indicates the
longest carbon
chain. Five
carbon atoms
= pentane.
1 2 3 4 5
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Organic ChemistryNaming Branched Chain Alkanes
H C
H
H
C
C
H
C
H
C
C
H HH
H
H
H
H HH
2,3-dimethylbutane
2,3-Dimethylbutane
1 2 3 4
Two methyl
groups (–CH3),
one bonded
to carbon
No. 2, and one
bonded to
carbon No. 3
of the longest
carbon chain.
Indicates the
longest carbon
chain. Four
carbon atoms
= butane.
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Organic ChemistryNaming Cyclic Alkanes
Cyclobutane
C C
C C
H
H
H
H H
H
H
H
cyclobutane
The prefix cyclo–
indicates that the
carbon atoms
are arranged in
a ring.
Indicates the
longest carbon
chain. Four
carbon atoms
= butane.
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Name FormulaRelative Molecular
Mass m.p. / C b.p. / C
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 ChemistryNaming Straight Chain Alkanes
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The melting points and boiling points of the alkanes
increases as the length of the carbon chain 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.
The melting points and boiling points of the alkanes
increases as relative molecular mass increases.
Organic ChemistryNaming Straight Chain Alkanes
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Organic ChemistryNaming 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.
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Organic ChemistryNaming 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.
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Organic ChemistryNaming 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.
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Organic ChemistryNaming 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.
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Organic ChemistryNaming Straight Chain Alkanes
H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
pentane
H C
H
H
C
C
C
C
H
H
H
H HH
H HH
2,2-dimethylpropane(or just dimethylpropane)
Pentane and 2,2-dimethylpropane are
isomers, i.e. they share the same
molecular formula (C5H12), but have
different structural formulae. Pentane boils
at 31.6 C, while 2,2-dimethylpropane boils
at 9.50 C. The difference in boiling points
is due to the difference in their surface
areas. The larger surface area of pentane
results in stronger intermolecular forces of
attraction (Van der Waals forces) between
the molecules, which require more energy
to overcome, hence increasing the
boiling point.
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How do I name the
alkenes,
halogenoalkanes,
alcohols and
carboxylic acids?
Organic Chemistry
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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 ChemistryNaming Alkenes
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C2H4
Ethene
C C
H
HH
H
Organic ChemistryNaming Alkenes
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C2H4
Ethene
Prefix:
Denotes the
number of
carbon atoms
in the molecule.
Suffix:
Denotes the
homologous series
that the compound
belongs to.
C C
H
HH
H
Organic ChemistryNaming Alkenes
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C3H6
H
C
H
C
H
C
H
H
H
Organic ChemistryNaming Alkenes
Propene
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C4H8
But-1-ene
H
C
H
C
H
C
H
H
C
H
H
H1 2 3 4
Organic ChemistryNaming Alkenes
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C4H8
But-1-eneNumber:
Indicates the
location of the
C=C bond
within the
molecule.
H
C
H
C
H
C
H
H
C
H
H
H1 2 3 4
Organic ChemistryNaming Alkenes
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C C
H H
C C
H
H
H
H
H
H
1 2 3 4
Organic ChemistryNaming Alkenes
C4H8
But-2-ene
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C C
H H
C C
H
H
H
H
H
H
1 2 3 4
Organic ChemistryNaming Alkenes
C4H8
But-2-eneNumber:
Indicates the
location of the
C=C bond
within the
molecule.
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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 ChemistryNaming Halogenoalkanes
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CH3Cl
ChloromethaneH
CH
H
Cl
Organic ChemistryNaming Halogenoalkanes
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CH3Cl
Chloromethane
Prefix:
Indicates the
Group VII
element that
is present in
the compound,F = fluoro-
Cl = chloro-
Br = bromo-
I = Iodo-
Suffix:
Denotes the
number of
carbon atoms
in the molecule.
H
CH
H
Cl
Organic ChemistryNaming Halogenoalkanes
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C2H5Br
H C
H
H
C
H
H
Br
Organic Chemistry
Bromoethane
Naming Halogenoalkanes
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C3H7Cl
1-Chloropropane
H C
H
H
C
H
H
C
H
H
Cl123
Organic ChemistryNaming Halogenoalkanes
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C3H7Cl
1-Chloropropane
Number:
Indicates the
location of the
chlorine atom
within the
molecule.
H C
H
H
C
H
H
C
H
H
Cl123
Organic ChemistryNaming Halogenoalkanes
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H C
H
H
C
Cl
H
C
H
H
H1 2 3
Organic Chemistry
C3H7Cl
2-Chloropropane
Naming Halogenoalkanes
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H C
H
H
C
Cl
H
C
H
H
H1 2 3
Organic Chemistry
C3H7Cl
2-Chloropropane
Number:
Indicates the
location of the
chlorine atom
within the
molecule.
Naming Halogenoalkanes
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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 ChemistryNaming Alcohols
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CH3OHMelting Point = –97.6 C
Boiling Point = 64.7 C
Methanol
Prefix:
Denotes the
number of
carbon atoms
in the molecule.
Suffix:
Denotes the
homologous series
that the compound
belongs to.
H C
H
H
O
H
Organic ChemistryNaming Alcohols
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C2H5OHMelting Point = –114 C
Boiling Point = 78.2 C
Ethanol
H C
H
H
C
H
H
O
H
Organic ChemistryNaming Alcohols
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C3H7OHMelting Point = –126 C
Boiling Point = 97.5 C
Propan-1-olNumber:
Indicates the
location of the
O–H group
within the
molecule.
C C
H
H
C
H
H
O
H
H
H
H123
Organic ChemistryNaming Alcohols
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C3H7OH
Propan-1-ol
C C
H
H
C
H
H
O
H
H
H
H123
Organic ChemistryNaming Alcohols
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C3H7OH
Propan-1-olNumber:
Indicates the
location of the
O–H group
within the
molecule.
C C
H
H
C
H
H
O
H
H
H
H123
Organic ChemistryNaming Alcohols
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C C
O
H
C
H
H
H
H
H
H
H
1 2 3
Organic ChemistryNaming Alcohols
C3H7OH
Propan-2-ol
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C C
O
H
C
H
H
H
H
H
H
H
1 2 3
Organic ChemistryNaming Alcohols
C3H7OH
Propan-2-olNumber:
Indicates the
location of the
O–H group
within the
molecule.
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Remember, the carboxylic acids are weak acids, i.e.
they only partially ionise when dissolved in water.
CH3COOH Ý CH3COO– + H+
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.
Organic ChemistryNaming Carboxylic Acids
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CHOOH
Methanoic Acid
H C
O H
O
Organic ChemistryNaming Carboxylic Acids
By default, the C of COOH is always No. 1.
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CHOOH
Methanoic Acid
Prefix:
Denotes the
number of
carbon atoms
in the molecule.
Suffix:
Denotes the
homologous series
that the compound
belongs to.
H C
O H
O
Organic ChemistryNaming Carboxylic Acids
By default, the C of COOH is always No. 1.
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H C
H
H
C
O H
O
Organic ChemistryNaming Carboxylic Acids
CH3COOH
Ethanoic Acid
By default, the C of COOH is always No. 1.
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C C
H
H
C
O H
OH
H
H
Organic ChemistryNaming Carboxylic Acids
C2H5COOH
Propanoic Acid
By default, the C of COOH is always No. 1.
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Organic ChemistryNaming Carboxylic Acids
H C
H
H
C
H
H
C
H
H
C
O H
O
C3H7COOH
Butanoic Acid
By default, the C of COOH is always No. 1.
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Organic ChemistryHierarchy of Functional Groups in Naming Compounds
C
O H
O
C O H
C C
C Halogen
Higher Priority
Lower Priority
Carboxylic Acid
Alcohol
Alkene
Halogenoalkane
Higher priority groups have lower numbers
assigned to them when naming.
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Organic ChemistryHierarchy of Functional Groups in Naming Compounds
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–CH2–CH2OH
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.
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Organic ChemistryHierarchy of Functional Groups in Naming Compounds
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.
CH2Cl–CHCl–CH2–COOH
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.
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What is the origin
of the organic
compounds that
are used by
chemists?
Organic Chemistry
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Organic Chemistry
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Organic Chemistry
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.
Origin of Crude Oil (Petroleum)
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.
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Organic ChemistryOrigin of Crude Oil (Petroleum)
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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 ChemistryOrigin of Crude Oil (Petroleum)
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Diagram to illustrate some uses of the different
fractions that are separated from crude oil.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Petrol – C5H12 to C10H22 – is an important fraction that
is separated from crude oil by fractional distillation.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Petroleum
GasC1 – C4
b.p. = < 40 C
PetrolC5 – C10
b.p. = 40 – 75 C
NaphthaC7 – C14
b.p. = 90 – 150 C
Paraffin
(Kerosene)
C9 – C16
b.p. = 150 – 240 C
Diesel
Oil
C15 – C25
b.p. = 220 – 250 C
Lubricating
Oil
C20 – C35
b.p. = 300 – 350 C
Bitumen> C70
b.p. = > 350 C
Crude
Oil
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Name of
Fraction
Number of
Carbon Atoms
Boiling Point
/ C
Use of
Fraction
Petroleum Gas C1 – C4 < 40Fuel for cooking and
heating.
Petrol C5 – C10 40 – 75 Fuel for motorcars.
Naphtha C7 – C14 90 – 150Feedstock for the
chemical industry.
Paraffin
(Kerosene)C9 – C16 150 – 240
Fuel for aircraft,
cooking and heating.
Diesel Oil C15 – C25 220 – 250Fuel for buses,
lorries and trains.
Lubricating Oil C20 – C35 300 – 350For lubricating
machines.
Bitumen > C70 > 350For making road
surfaces and roofing.
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Octane Hexane Ethene
H C
H
H
C
H
C
H
C
H
C
H
C
H
C
H
C
H
H
H H H H H H H
H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H C C
H
H H
H
+
HighTemperature /
Catalyst
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.
Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Al2O3
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Organic ChemistryFractional 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.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
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Organic ChemistryFractional 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.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
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Organic ChemistryFractional 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.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
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Organic ChemistryFractional 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.
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Organic ChemistryFractional Distillation of Crude Oil (Petroleum)
Pollutants can be removed from car exhaust fumes
using catalytic converters.
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What are
isomers?
Organic Chemistry
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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 ChemistryIsomers
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Organic ChemistryThere are Two Isomers of C4H10:
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H C
H
H
C
H
H
C
H
H
C
H
H
H
butane
H C
H
H
C
C
H
C
H
H
H
H HH
2-methylpropane(or just methylpropane)
Organic ChemistryThere are Two Isomers of C4H10:
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H C
H
H
C
H
H
C
H
H
C
H
H
H
butane
C C
C
H
H
C
H
H
H
H
H
H HH
This is butane not1-methylpropane
C
C C
C
H
H
H
H
H HH
H HH
This is butane not1,2-dimethylethane
H C
H
H
C
H
H
C
H
C
H
H HH
This is butane not1-methylpropane
H C
H
H
C
C
H
C
H
H
H
H HH
2-methylpropane(or just methylpropane)
Organic ChemistryThere are Two Isomers of C4H10:
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Organic ChemistryWhat are the Isomers of C4H9Br?
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Br C
H
H
C
C
H
C
H
H
H
H HH
1-bromo-2-methylpropane(or just 1-bromomethylpropane)
Br C
H
H
C
H
H
C
H
H
C
H
H
H
1-bromobutane
H C
H
H
C
Br
H
C
H
H
C
H
H
H
2-bromobutane
H C
H
H
C
C
Br
C
H
H
H
H HH
2-bromo-2-methylpropane(or just 2-bromomethylpropane)
Organic ChemistryWhat are the Isomers of C4H9Br?
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Organic ChemistryWhat are the Isomers of C5H12?
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
pentane
H C
H
H
C
C
H
C
H
H
C
H HH
H
H
H
2-methylbutane(or just methylbutane)
H C
H
H
C
C
C
C
H
H
H
H HH
H HH
2,2-dimethylpropane(or just dimethylpropane)
Organic ChemistryWhat are the Isomers of C5H12?
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Organic ChemistryWhat are the Isomers of C6H14?
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H C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
C
H
H
H
hexane
H C
H
H
C
C
H
C
H
H
C
H HH
H
H
C
H
H
H
2-methylpentane
C C
H
H
C
C
H
C
H
H
C
H HH
H
H
H
H
H
H
3-methylpentane
H C
H
H
C
C
C
C
H
H
C
H HH
H
H
H
HHH
2,2-dimethylbutane
H C
H
H
C
C
H
C
H
C
C
H HH
H
H
H
H HH
2,3-dimethylbutane
Organic ChemistryWhat are the Isomers of C6H14?
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Organic ChemistryWhat are the Isomers of C4H8?
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Geometric Isomers!
C C
H
H
H
C
H
H
C
H
H
H
but-1-ene
H
CH
H
C
H
C
H
C
H
H
H
but-2-ene
C C
CH
H C H
H
HH
H H
trans-but-2-ene
C C
CH
H H
HC
H H H H
cis-but-2-ene
C C
C
C
H
H
H
H HH
H
H
2-methylprop-1-ene(or just methylpropene)
C C
C C
H
H
H
H H
H
H
H
cyclobutane
C C
C
C
H
H
H
H H
H
H H
methylcyclopropane
Organic ChemistryWhat are the Isomers of C4H8?
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How do I calculate
the formula of an
organic compound
from its percentage
composition?
Organic Chemistry
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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 ChemistryCalculation of Formula from Percentage Composition
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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 = 14.3How 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 ChemistryCalculation of Formula from Percentage Composition
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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 ChemistryCalculation of Formula from Percentage Composition
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Step 3: This gives the compound’s empirical
formula which is the most simple ratio of
elements in the compound.
CH2
Organic ChemistryCalculation of Formula from Percentage Composition
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Step 4: Calculate the relative molecular mass
of the compound’s empirical formula.
= C + (2 H)
= 12.0 + (2 1.0)
= 14.0
Organic ChemistryCalculation of Formula from Percentage Composition
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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 ChemistryCalculation of Formula from Percentage Composition
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Step 6: Multiply the empirical formula by the
answer to Step 5 to determine the compound’s
molecular formula.
= CH2 3.00
C3H6
Organic ChemistryCalculation of Formula from Percentage Composition
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C C
H
C
H
H
H
H
H
Propene
C C
C
H H
HH
H H
Cyclopropane
Organic ChemistryCalculation of Formula from Percentage Composition
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How are the
reactions of
organic
compounds
classified?
Organic Chemistry
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Organic reactions can be classified
into (at least) three main types:
Addition.
Elimination.
Substitution.
Organic ChemistryClassification of Organic Reactions
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H
C
H
C
H
H
H C
Br
H
C
Br
H
HBr2+
Unsaturated Saturated
Ethene 1,2-Dibromoethane
Organic ChemistryClassification of Organic Reactions
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H
C
H
C
H
H
H C
Br
H
C
Br
H
HBr2+
Unsaturated Saturated
Ethene 1,2-Dibromoethane
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
Br
H
C
H
C
H
H
+ +KOH(ethanol) +KBr H2O
UnsaturatedSaturated
Bromoethane Ethene
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
Br
H
C
H
C
H
H
+ +KOH(ethanol) +KBr H2O
UnsaturatedSaturated
Bromoethane Ethene
Organic ChemistryClassification of Organic Reactions
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Bromoethane
H C
H
H
C
H
H
Br H C
H
H
C
H
H
OH+ KOH(aqueous) + KBr
Substitute
Ethanol
Organic ChemistryClassification of Organic Reactions
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Bromoethane
H C
H
H
C
H
H
Br H C
H
H
C
H
H
OH+ KOH(aqueous) + KBr
Substitute
Ethanol
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
Br
H
C
Br
H
HC
H
C
H
H
C
H
H
H
+ Br2
Propene 1,2-Dibromopropane
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
Br
H
C
Br
H
HC
H
C
H
H
C
H
H
H
+ Br2
Propene 1,2-Dibromopropane
Organic ChemistryClassification of Organic Reactions
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Bromo-
cyclohexane
C
CC
C
CC
H H
H H
H
HH
H
H
H
C
CC
C
CC
H H
H H
H
Br
H
HH
H
H
H
KOH(ethanol)+ + KBr H2O+
Cyclohexene
Organic ChemistryClassification of Organic Reactions
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Bromo-
cyclohexane
C
CC
C
CC
H H
H H
H
HH
H
H
H
C
CC
C
CC
H H
H H
H
Br
H
HH
H
H
H
KOH(ethanol)+ + KBr H2O+
Cyclohexene
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
C
H
H
C
H
H
HC
H
C
H
C
H
H
H
C
H
H
H + H2
But-1-ene Butane
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
C
H
H
C
H
H
HC
H
C
H
C
H
H
H
C
H
H
H + H2
But-1-ene Butane
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
C
H
C
H
H
Br
H H
C
H
C
H
H
C
H
H
NC
H
H
H
H
H
H
+ NH3 HBr+
1-Bromobutane Butyl-1-amine
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
C
H
C
H
H
Br
H H
C
H
C
H
H
C
H
H
NC
H
H
H
H
H
H
+ NH3 HBr+
1-Bromobutane Butyl-1-amine
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
H
C
H
H
Cl C
H
C
H
C
H
H
H
HKOH(ethanol)+ + KCl H2O+
1-Chloropropane Propene
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
H
C
H
H
Cl C
H
C
H
C
H
H
H
HKOH(ethanol)+ + KCl H2O+
1-Chloropropane Propene
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
C
H
C
H
H
H H C
H
H
C
H
H
C
Br
H
C
H
H
H+ HBr
But-2-ene 2-Bromobutane
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
C
H
C
H
H
H H C
H
H
C
H
H
C
Br
H
C
H
H
H+ HBr
But-2-ene 2-Bromobutane
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
H
C
H
H
Cl
H
CH
H
C
H
H
C
H
H
OHH2O HCl+ +
1-Chloropropane Propan-1-ol
Organic ChemistryClassification of Organic Reactions
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H
CH
H
C
H
H
C
H
H
Cl
H
CH
H
C
H
H
C
H
H
OHH2O HCl+ +
1-Chloropropane Propan-1-ol
Organic ChemistryClassification of Organic Reactions
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Butan-1-ol
C C
H
H
C
H
H
OH
H
H
C
H
H
H C
H
C
H
C
H
H
H
C
H
H
H + H2O
But-1-ene
Organic ChemistryClassification of Organic Reactions
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Butan-1-ol
C C
H
H
C
H
H
OH
H
H
C
H
H
H C
H
C
H
C
H
H
H
C
H
H
H + H2O
But-1-ene
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
Br H C
H
H
C
H
H
C NKC N+ + KBr
Bromoethane Propanenitrile
Organic ChemistryClassification of Organic Reactions
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H C
H
H
C
H
H
Br H C
H
H
C
H
H
C NKC N+ + KBr
Bromoethane Propanenitrile
Organic ChemistryClassification of Organic Reactions
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1-Bromo-2-
methylpropane
or
1-Bromo-
methylpropane
H
CH
H
C
C
H
C
H
H
Br
HHH
C
H
C
C
C
H
H
H
H
H HH
KOH(ethanol)+ + KBr H2O+
2-Methylpropene
or Methylpropene
Organic ChemistryClassification of Organic Reactions
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1-Bromo-2-
methylpropane
or
1-Bromo-
methylpropane
H
CH
H
C
C
H
C
H
H
Br
HHH
C
H
C
C
C
H
H
H
H
H HH
KOH(ethanol)+ + KBr H2O+
2-Methylpropene
or Methylpropene
Organic ChemistryClassification of Organic Reactions
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Benzene
C
CC
C
CC
C
H
H H
H H
H HH
C
CC
C
CC
H
H
H H
H H H
CH
H
Br HBr+ +
Methylbenzene
Organic ChemistryClassification of Organic Reactions
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Benzene
C
CC
C
CC
C
H
H H
H H
H HH
C
CC
C
CC
H
H
H H
H H H
CH
H
Br HBr+ +
Methylbenzene
Organic ChemistryClassification of Organic Reactions
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C
CC
C
CC
H H
H H
H
HH
H
H
H
C
CC
C
CC
H H
H HH
H
H
H H
H
H
OH+ H2O
Cyclohexene Cyclohexanol
Organic ChemistryClassification of Organic Reactions
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C
CC
C
CC
H H
H H
H
HH
H
H
H
C
CC
C
CC
H H
H HH
H
H
H H
H
H
OH+ H2O
Cyclohexene Cyclohexanol
Organic ChemistryClassification of Organic Reactions
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Organic Chemistry
Presentation on
Organic Chemistry
By Dr. Chris Slatter
Nanyang Girls’ High School
2 Linden Drive
Singapore
288683
14th February 2016