TOPIC 11
NOTES (ORGANIC CHEMISTRY)
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SYLLABUS CONTENT
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11. ORGANIC CHEMISTRY
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11. ORGANIC CHEMISTRY
Organic chemistry is the branch of chemistry that
deals with carbons compounds.
ORGANIC COMPOUNDS
Compounds found in living organisms.
Examples: sugar, fats, plant oils, urea
FUNCTIONAL GROUPS
CHARACTERISTICS OF ORGANIC
COMPOUNDS Functional groups is the special group of atoms
o All contain carbon element. available in homologous series compounds which
o Most come with hydrogen. responsible for the chemical properties of the
o Others with oxygen, nitrogen and compound
halogens.
Example:
USES OF ORGANIC COMPOUNDS Alkane with C – C single bond.
Fuels, plastic, rubber, detergents, insecticides, Alkene with C = C double bond.
most medicines. Alcohol with – OH functional group.
Carboxylic acid with – COOH functional
group.
HOMOLOGOUS SERIES
A family of organic compounds with same
general formula and chemical properties.
Example:
o Alkane with general formula CnH2n+2 HYDROCARBONS
o Alkene with general formula CnH2n
Organic compounds which contain carbon (C)
o Alcohol with general formula CnH2n+1 OH
and hydrogen (H) only.
o Carboxylic acid with general formula
CnH2n+1 COOH
CHARACTERISTICS OF A HOMOLOGOUS SERIES SATURATED HYDROCARBONS
1. All members of homologous series have Organic compound containing C - C single bond,
same general formula. said to be saturated. They only have single bond
2. Formula of each member differs by –CH2 (–) only.
group.
3. Physical properties changes gradually by UNSATURATED HYDROCARBONS
the increase of carbon atoms.
4. The members have similar chemical Organic compound containing C = C double
properties. bond, said to be unsaturated.
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11.1 ALKANES
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The majority of compounds found in the mixture of hydrocarbons we call crude oil are alkanes.
Alkanes have general formula CnH2n+2
Alkanes are saturated hydrocarbons (compound containing C - C single bond).
Next alkane formula differ by –CH2 atoms.
Alkanes are unreactive.
MEMBERS OF THE SERIES
NUMBER OF CARBONS NAME OF ALKANE MOLECULAR FORMULA
n=1 Methane CH4
n=2 Ethane C2H6
n=3 Propane C3H8
n=4 Butane C4H10
PHYSICAL PROPERTIES OF ALKANES
Name Molecular Formula Melting Point (0C) Boiling Point (0C) State at r.t.p Density (g/cm3)
Methane CH4 -182 -162 0.00068
Ethane C2H6 -172 -89 Gas 0.00127
Propane C3H8 -187 -42 0.00186
Butane C4H10 -138 -0.5 0.00245
Pentane C5H12 -130 36 0.63
Hexane C6H14 -95 69 0.66
. . . . Liquid .
. . . . .
. . . . .
Heptadecane C17H36 22 292 0.77
Octadecane C18H38 28 308 Solid 0.78
Nonadecane C19H40 32 320 0.78
o Melting points and boiling points increase down the series
o Alkane density increases down the series.
o Alkanes become more viscous (uneasily flow) going down the series
o Alkanes become less flammable down the series as B.P. becomes larger.
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11.1.1 SOURCES OF THE ALKANES
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Crude oil is a complex mixture of hydrocarbons – alkanes.
The complex mixture of hydrocarbons in crude oil can be separated into fractions by the technique of
fractional distillation.
11.1.2 REACTIONS OF ALKANES
The alkanes are generally unreactive compounds.
11.1.2.1 COMBUSTION OF ALKANES
Alkanes are often used as fuels. Burning of an alkane in the presence of oxygen is known as
combustion.
1. COMPLETE COMBUSTION
o Complete combustion (given sufficient oxygen) of alkane (any hydrocarbon) produces carbon
dioxide and water.
C3H8 + 5O2 3CO2 + 4H2O
2. INCOMPLETE COMBUSTION
o Incomplete combustion (where there isn't enough oxygen present) can lead to the
formation of carbon or carbon monoxide and water.
C3H8 + 3/2O2 3CO + 4H2O
OR C3H8 + 2O2 3C + 4H2O
11.1.2.2 SUBSTITUTION REACTIONS OF ALKANES (CHLORINATION OF ALKANE)
Alkanes undergo a substitution reaction with halogens in the presence of light. There is no
reaction in the dark.
o Substitution reaction – the reaction in which one or more atoms replace other atoms in a
molecule (Chlorine molecule replaces alkane hydrogen atom with chlorine atom).
o Light is needed to break covalent bond between chlorine molecules.
Example: Methane reacts with halogen molecules such as chlorine and bromine. This reaction is
a substitution reaction because one of the hydrogen atoms from the methane is replaced by a chlorine
atom.
CH4 + Cl2 CH3Cl + HCl
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Example:
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Worksheet 1
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REACTION OF ALKANES WITH CHLORINE
EXAMPLE
REACTION OF METHANE WITH CHLORINE
Light is needed
MOLECULAR
CH4 + Cl2 CH3Cl + HCl
STRUCTURAL
REACTION OF ETHANE WITH CHLORINE
MOLECULAR
STRUCTURAL
REACTION OF PROPANE WITH CHLORINE
MOLECULAR
STRUCTURAL
REACTION OF BUTANE WITH CHLORINE
MOLECULAR
STRUCTURAL
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11.2 ALKENES
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Alkenes are unsaturated hydrocarbons.
Alkenes have general formula CnH2n (with one double bond).
Next alkane formula differ by –CH2 atoms.
MEMBERS OF THE SERIES
NUMBER OF CARBONS NAME OF ALKANE MOLECULAR FORMULA
n=2 Ethene C2H4
n=3 Propene C3H6
n=4 Butene C4H8
11.2.1 REACTIONS OF ALKENES
11.2.1.1 COMBUSTION OF ALKENES
Burning of an alkene in the presence of oxygen is known as combustion.
1. COMPLETE COMBUSTION
o Complete combustion (given sufficient oxygen) of alkane (any hydrocarbon) produces
carbon dioxide and water.
C2H4 + 3O2 2CO2 + 2H2O
2. INCOMPLETE COMBUSTION
o Incomplete combustion (where there isn't enough oxygen present) can lead to the
formation of carbon or carbon monoxide and water.
C2H4 + 2O2 2CO + 2H2O
OR C2H4 + O2 2C + 2H2O
11.2.2 ADDITION REACTIONS OF THE ALKENES
Alkenes undergo an addition reaction.
o Addition reaction – the reaction in which two or more molecules to form a single product.
1. ADDITION OF HYDROGEN
Alkenes react with hydrogen to form alkanes, called hydrogenation. Must use nickel as catalyst
and heat (140 °C).
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2. ADDITION OF HALOGENS X2(aq) (ADDITION OF BROMINE Br2 (aq))
If we bubble an alkene through a solution of chlorine or bromine at room temperature, we get an
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addition reaction.
The colour of the halogen molecules in solution, which is pale green for chlorine water and
orange/yellow for bromine water, is removed.
In fact, bromine water is used to test for the presence of the C = C bond in compounds. The
compound to be tested is shaken with bromine water. If it is unsaturated, the bromine water will
be decolorised.
Bromine adds to C = C double bond of alkane molecules to form C2H4Br2.
3. ADDITION OF STEAM, H2O(g)
Alkene reacts with water, in the form of steam, to produce alcohol.
Alkene + steam is passed over concentrated phosphoric acid (H3PO4) catalyst, temperature of
330oC and a pressure of 6 MPa.
4. POLYMERIZATION
The joining of several identical alkene molecules to form a big molecule
Foods and Unsaturated Compounds
The Manufacture of Margarine Polyunsaturated food – food containing C=C bond in their molecules Eg:
Vegetable oil
To produce margarine:
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Hydrogen is reacted with vegetable oil with presence of nickel catalyst and heat, which adds to C=C bond,
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increasing the molecular mass of the compound
With increase in mass, the compound has higher boiling point. Therefore, margarine is solid at room
temperature.
Since only some C=C bonds react with hydrogen, margarine is partially hydrogenated and each has
different hardness, depending on the number of C=C bonds.
ISOMERISM
Isomers are compounds with same molecular formula but different structural formula.
Due to different chain length, they have different physical properties (e.g. boiling point).
For example
Hexane has several chain isomers, all with the molecular formula C6H14.
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ALCOHOLS
Are homologous series with general formula CnH2n+1OH
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They have –OH functional group (hydroxyl group)
All alcohols end with suffix –ol
MEMBERS OF THE SERIES
NUMBER OF CARBONS NAME OF ALCOHOLS MOLECULAR FORMULA
n=1 Methanol CH3OH
n=2 Ethanol C2H5OH
n=3 Propanol C3H7OH
n=4 Butanol C4H9OH
PREPARATION OF ALCOHOLS
FERMENTING GLUCOSE
Fermentation is breakdown of sugars into smaller molecules by microorganisms.
Temperature is kept constant at 37oC to prevent destruction of yeast at higher temperatures.
Oxygen is removed by limewater and carbon dioxide is produced during fermentation.
Alcohol is separated from solution by fractional distillation.
REACTING ETHENE WITH STEAM
Ethene and steam are passed over phosphoric acid H3PO4 (as a catalyst) under high temperature of 300oC
and pressure of 65 atm. Since this is reversible reaction, both ethene and water are produced aside from
ethanol. The ethanol is separated by fractional distillation.
USES OF ALCOHOL
As organic solvent; alcoholic drink; preservatives; vehicle fuel
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REACTIONS OF ALCOHOL
COMBUSTION
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Alcohols burn in air to produce carbon dioxide and water.
E.g. combustion of ethanol
OXIDATION
1. Alcohol can be prepared in laboratory by warming alcohol with oxidizing agent (e.g. acidified
potassium chromate(VI). The product is carboxylic acid and water.
E.g. oxidation of ethanol produces water and ethanoic acid.
2. Alcohol can be oxidized when left in air with bacterial enzymes as catalyst. The products are
carboxylic acid and water.
E.g. ethanol produces water and ethanoic acid when left in air.
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CARBOXYLIC ACIDS
Homologous series with general formula CnH2n+1COOH (first serie, n = 0, ascending)
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They have –COOH functional group (carboxyl group)
All carboxylic acids end with suffix –oic acid
MEMBERS OF THE SERIES
NUMBER OF CARBONS NAME OF CARBOXYLIC MOLECULAR FORMULA
ACID
n=0 Methanoic acid HCOOH
n=1 Ethanoic acid CH3COOH
n=2 Propanoic acid C2H5COOH
n=3 Butanoic acid C3H7COOH
PREPARATION OF CARBOXYLIC ACID
1. FROM NATURAL GAS (CH4)
Natural gas is passed over air and catalyst to form ethanoic acid and water.
E.g. production of ethanoic acid from methane
2. OXIDATION
1. Alcohol can be prepared in laboratory by warming alcohol with oxidizing agent (e.g. acidified
potassium chromate(VI). The product is carboxylic acid and water.
E.g. oxidation of ethanol produces water and ethanoic acid.
2. Alcohol can be oxidized when left in air with bacterial enzymes as catalyst. The products are
carboxylic acid and water.
E.g. ethanol produces water and ethanoic acid when left in air.
PROPERTIES OF CARBOXYLIC ACIDS
1. Carboxylic acids are weak acids (partially ionises in water)
2. Carboxylic acids react with metals to form metal ethanoate (salt) and hydrogen
E.g. Reaction between calcium and ethanoic acid forming calcium ethanoate and hydrogen
3. Carboxylic acids react with bases to form salt and water (neutralization)
E.g. Ethanoic acid reacts with sodium hydroxide to form sodium ethanoate and water.
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4. Carboxylic acids react with carbonates to form salt, carbon dioxide and water.
E.g. Ethanoic acid reacts with sodium carbonate to form sodium ethanoate, carbon dioxide and water.
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ESTERIFICATION
Ester is organic compound made from carboxylic acid and alcohol with the removal of one molecule of
water. Sulfuric acid is added as catalyst then heat mixture. The reaction is reversible. We can add sodium
hydroxide and heat mixture to obtain carboxylic acid and alcohol from ester. This is HYDROLYSIS.
ESTER NOMENCLATURE:
Ester name is [alcohol] yl [carboxylic acid] oate.
For instance, example above is propyl Ethaoate, where “propyl” is from propaol; “Ethanoate” is from
ehtanoic acid.
ESTERIFICATION WORKSHEET
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
Methanol Methanoic Acid Methyl Methanoate WATER
CH3OH HCOOH HCOOCH3 H2O
STRUCTURAL EQATION
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ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
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Methanol Ethanoic Acid Methyl Ethanoate WATER
CH3OH CH3COOH CH3COOCH3 H2O
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
Methanol Propanoic Acid Methyl Propanoate WATER
CH3OH C2H5COOH C2H5COOCH3 H2O
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
Methanol Butanoic Acid Methyl Butanoate WATER
CH3OH C3H7COOH C3H7COOCH3 H2O
STRUCTURAL EQATION
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ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
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STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
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ALCOHOL CARBOXYLIC ACID ESTER WATER
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MOLECULAR EQUATION
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
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ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
ALCOHOL CARBOXYLIC ACID ESTER WATER
MOLECULAR EQUATION
STRUCTURAL EQATION
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POLYMERISATION
ADDITION POLYMERISATION
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Alkenes undergo addition polymerization, in which small molecules (monomers) join together to form
large molecules (polymer).
Example: Formation of poly(ethene) from ethene.
Repeat unit is the simplest part of the polymer which is repeated many times to form the polymer.
Some plastic variations and their uses are shown:
Poly (ethene)
Uses: plastic bags, plastic bottles, etc.
Poly (chloroethene)
Uses: plastic bags, plastic pipes, etc
Poly (phenylethene)
Poly (tetrafluoroethene)
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CONDENSATION POLYMERISATION
Condensation Polymerisation is the joining of monomers together to form polymers along with the
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elimination of water molecules.
NYLON
Dicarboxylic acid and diamine undergo condensation polymerisation to form nylon.
The linkage between monomers in nylon is called amide linkage. Therefore we can also call nylon as
polyamide.
Today, we use nylon as:
a replacement of stockings and manufacture of garments to replace silk
make tents and parachutes due to strength
fishing lines
rugs and carpets
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TERYLENE
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Dicarboxylic acid and diol undergo condensation polymerisation to form terylene.
The linkage between the monomers in terylene is called ester linkage. Therefore we can call this polymer as
polyester.
Today, we use terylene in fabrics as it’s strong, resists stretching and sinking and doesn’t crumple when
washed.
PROBLEMS ASSOCIATED WITH PLASTICS
Plastics are non-biodegradable
They cannot be decomposed by bacteria. Therefore, many plastic waste will pollute the Earth
Plastics produce toxic gas (such as hydrogen chloride) when burnt and this contributes to acid rain.
Plastics produce carbon dioxide when burnt so it increases global warming.
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NATURAL MACROMOLECULES
CARBOHYDRATES
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Carbohydrates contain carbon, hydrogen & oxygen. The simplest carbohydrate is C6H12O6 (glucose).
Glucose polymerise each other to form starch.
Starch can also be broken down into glucose by heating with sulfuric acid. This is HYDROLYSIS.
PROTEINS
Proteins have similar linkage to that of a nylon. Only that their monomers are only amino acids joined
together. They are formed by condensation polymerisation.
Proteins can be called as polyamide as it has amide linkage. Proteins can also be broken down into amino
acids by boiling protein with sulfuric acid. This adds water molecule into the polymer.
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FATS
Fats have similar linkage to that of a terylene (ester linkage). Only that their monomers consists of glycerol
and fatty acids.
Fats can also be broken down to sodium salts of fatty acids and glycerol by boiling it with an acid or alkali.
This is HYDROLYSIS.
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