Introduction to Organic Chemistry
Organic chemistry is the chemistry of carbon compounds. Due to the ability of carbon to form chains of atoms, and for other atoms or groups of atoms to be attached to these chains, there are a huge number of carbon compounds.
All organic compounds contain carbon together with one or more other elements such as hydrogen, oxygen, nitrogen, sulphur and the halogens.
Normally every compound of carbon is an organic compound. Even after discovering that these compounds could be synthesized in the laboratory, the definition that they are organic (of organic nature, that is, they originate from living things) has been retained. However, for conventional and historic reasons, some of the simpler compounds such as carbon dioxide (CO2) carbonates, carbon monoxide (CO3) are usually studied with other non-carbon compounds in Inorganic Chemistry.
Difference between Organic from Inorganic Chemistry
Distinguish organic from inorganic chemistry
Organic chemistry is the chemistry of carbon compounds. All organic compounds contain carbon and other elements such as H, O, N, S and the halogens.
Normally every compound of carbon is an organic compound. Examples of organic compounds/substances are plastics, milk, carbohydrates, lipids, proteins, sugar and hydrocarbons. Inorganic substances includes table salt, CO2, diamond, iron and water.
The Importance of Organic Chemistry in Life
Explain the importance of organic chemistry in life
Carbon is the most unusual atom. It has the ability to join up to itself and form very long chains of atoms. Without this ability, life on Earth would not exist because the molecules that make our bodies contain mostly long chains of carbon atoms.
All living things contain carbon compounds. Raw materials such as oil and coal, derived from living things, are also based on carbon. Our modern society is very much dependent on organic chemistry to make the fuels and materials that we use in every day of our lives. In particular, polymers, large molecules obtained from alkanes, have very widespread use. Without alkanes from crude oil our transport system would be impossible.
We also need various fractions obtained from crude oil (petrol, diesel, kerosene, oil, natural gas, etc.) to run motor vehicles and other machines to simplify our work and life.
In brief, the compounds obtained from crude oil have thousands of different uses, for example:
- some are used as fuel or converted into fuels;
- some
are used for making detergents, dyes, drugs, paints, and cosmetics; and
yet some are used for making polyethene, polyvinyl chloride (PVC) and
other plastics.
The Origin of Organic Compounds
Explain the origin of organic compounds
Fossil
fuels were formed in the Earth’s crust from material that was once
living. Coal comes from fossils of plant material. Crude oil and natural
gas are formed from bodies of marine microorganisms. The formation of
these fuels took place over geological periods of time (many millions of
years).
fuels were formed in the Earth’s crust from material that was once
living. Coal comes from fossils of plant material. Crude oil and natural
gas are formed from bodies of marine microorganisms. The formation of
these fuels took place over geological periods of time (many millions of
years).
Crude
oil is one of the world’s major natural resources. The oil is the
result of a process that began up to 400 million years ago. Prehistoric
marine organisms died and sunk to the sea bed and were covered by mud
and sand. The change into crude oil and natural gas was brought about by
high pressure, high temperature and bacteria acting over millions of
years. The original organic material broke down into hydrocarbons.
Compression of the mud above the hydrocarbon mixture transformed it into
shale. Then geological movements and pressure changed this shale into
harder rocks, squeezing out the oil and gas. The oil and gas moved
upwards through the porous rocks, moving from high- pressure to
low-pressure conditions. Sometimes they reached the surface, but often
they became trapped by a layer of non porous rock. Reservoirs of oil and
gas were created. These reservoirs are not lakes of oil or pockets of
gas. Instead, the oil or gas is spreadthroughout the pores in coarse
rocks such as sandstone or limestone the same as water is held in a
sponge.
oil is one of the world’s major natural resources. The oil is the
result of a process that began up to 400 million years ago. Prehistoric
marine organisms died and sunk to the sea bed and were covered by mud
and sand. The change into crude oil and natural gas was brought about by
high pressure, high temperature and bacteria acting over millions of
years. The original organic material broke down into hydrocarbons.
Compression of the mud above the hydrocarbon mixture transformed it into
shale. Then geological movements and pressure changed this shale into
harder rocks, squeezing out the oil and gas. The oil and gas moved
upwards through the porous rocks, moving from high- pressure to
low-pressure conditions. Sometimes they reached the surface, but often
they became trapped by a layer of non porous rock. Reservoirs of oil and
gas were created. These reservoirs are not lakes of oil or pockets of
gas. Instead, the oil or gas is spreadthroughout the pores in coarse
rocks such as sandstone or limestone the same as water is held in a
sponge.
The Fractional Distillation of Crude Oil
Describe the fractional distillation of crude oil
Crude
oil from an oilfield is separated from impurities such as sand and
water and is pumped through pipelines to the refinery. At the refinery,
fractional distillation is used to separate the crude oil into several
fractions, each fraction containing several hydrocarbons which boil
within a certain range of temperatures. These different boiling points
are roughly related to the number of carbon atoms in the hydrocarbon
(Table 2.1)
oil from an oilfield is separated from impurities such as sand and
water and is pumped through pipelines to the refinery. At the refinery,
fractional distillation is used to separate the crude oil into several
fractions, each fraction containing several hydrocarbons which boil
within a certain range of temperatures. These different boiling points
are roughly related to the number of carbon atoms in the hydrocarbon
(Table 2.1)
Separation
of the hydrocarbons takes place in a fractionating column
(fractionating tower). At the start of the refinery process, crude oil
is preheated to a temperature of 350–400°C and pumped in at
the base of the tower. As it boils, the vapour passes up the tower. It
passes through a series of bubble caps and cools as it rises further up
the column. The different fractions cool and condense at different
temperatures, and therefore at different heights in the column. The
fractions condensing at the different levels are collected on trays.
of the hydrocarbons takes place in a fractionating column
(fractionating tower). At the start of the refinery process, crude oil
is preheated to a temperature of 350–400°C and pumped in at
the base of the tower. As it boils, the vapour passes up the tower. It
passes through a series of bubble caps and cools as it rises further up
the column. The different fractions cool and condense at different
temperatures, and therefore at different heights in the column. The
fractions condensing at the different levels are collected on trays.
Thus,
vapour is rising and liquid falling at each level in the tower. As a
result very efficient fractionation occurs. Liquid is taken off at
several different levels, the higher the level, the lower the boiling
point of the fraction removed. Figure 2.2 shows the process of
separation of crude oil into different fractions.
vapour is rising and liquid falling at each level in the tower. As a
result very efficient fractionation occurs. Liquid is taken off at
several different levels, the higher the level, the lower the boiling
point of the fraction removed. Figure 2.2 shows the process of
separation of crude oil into different fractions.
After
fractional distillation, impurities are removed. The commonest impurity
is sulphur, which is removed and used to manufacture sulphuric acid. If
petrol (gasoline) containing sulphur is not purified before it is used
in an internal combustion engine, the exhaust fumes will contain oxides
of sulphur (SO2 and SO3). These are poisonous gases and will pollute the environment.
fractional distillation, impurities are removed. The commonest impurity
is sulphur, which is removed and used to manufacture sulphuric acid. If
petrol (gasoline) containing sulphur is not purified before it is used
in an internal combustion engine, the exhaust fumes will contain oxides
of sulphur (SO2 and SO3). These are poisonous gases and will pollute the environment.
Uses of different petroleum fractions
1.
Natural gas (refinery gas). The gas fractions consist of mainly
methane, ethane, propane, and butane. The methane and ethane are usually
burnt as fuel. The propane and butane are liquefied and are distributed
in high pressure gas cylinders and tanks to be used for lighting and
heating purposes.
Natural gas (refinery gas). The gas fractions consist of mainly
methane, ethane, propane, and butane. The methane and ethane are usually
burnt as fuel. The propane and butane are liquefied and are distributed
in high pressure gas cylinders and tanks to be used for lighting and
heating purposes.
2.
Petrol (motor gasoline). It is mainly used as a fuel in internal
combustion engines in motor vehicles. It is also used as a solvent for
grease stains and paints.
Petrol (motor gasoline). It is mainly used as a fuel in internal
combustion engines in motor vehicles. It is also used as a solvent for
grease stains and paints.
3. Naphtha. It is used as a raw material for making many chemicals and plastics.
4.
Kerosene (paraffin). It is used in homes as a fuel in paraffin lamps
and stoves for heating, lighting and cooking food. However, in addition
to its domestic use, it is used as a fuel for jet engines in aeroplanes.
It is also used as a detergent.
Kerosene (paraffin). It is used in homes as a fuel in paraffin lamps
and stoves for heating, lighting and cooking food. However, in addition
to its domestic use, it is used as a fuel for jet engines in aeroplanes.
It is also used as a detergent.
5. Diesel oil. It is used as a fuel in diesel engines (e.g. in diesel train engines, tractors, lorries, diesel car engines).
6.
Lubricating oil. It is used to make petroleum jelly (e.g. Vaseline). It
is also used as oil for lubricating moving parts of cars and other
machines.
Lubricating oil. It is used to make petroleum jelly (e.g. Vaseline). It
is also used as oil for lubricating moving parts of cars and other
machines.
7. Fuel oil. It is used as a fuel for power stations, ships and factories.
8. Paraffin waxes. They are used to make candles, polishes and waxed papers. They are also used in water proofing and as grease.
9.
Asphalt, bitumen. They are used to make protective coatings for road
surfaces and concrete roof tops, and also as binding agents for roofing
sheets.
Asphalt, bitumen. They are used to make protective coatings for road
surfaces and concrete roof tops, and also as binding agents for roofing
sheets.
Hydrocarbons
Hydrocarbons
are compounds containing hydrogen and carbon and no other element. That
is, a hydrocarbon has the molecular formula CxHy, x and being whole
numbers. For example, methane (CH4) ethane (C2H2) and benzene (C6H6) are
hydrocarbons.
are compounds containing hydrogen and carbon and no other element. That
is, a hydrocarbon has the molecular formula CxHy, x and being whole
numbers. For example, methane (CH4) ethane (C2H2) and benzene (C6H6) are
hydrocarbons.
The three Families of Hydrocarbons
Classify the three families of hydrocarbons
In
order to simplify the study of these compounds, chemists have grouped
them into families. The members of each family have characteristic
chemical properties and graded physical properties, such as boiling
point, etc. The main family members of hydrocarbons that we shall study
at this level are the alkanes, the alkenes and the alkynes.
order to simplify the study of these compounds, chemists have grouped
them into families. The members of each family have characteristic
chemical properties and graded physical properties, such as boiling
point, etc. The main family members of hydrocarbons that we shall study
at this level are the alkanes, the alkenes and the alkynes.
Alkanes
The
members of this group of hydrocarbons are distinguished by possessing
the general molecular formula Cn H2n+2, where is 1, 2, 3, etc., for
successive members of the group. The first member of the series (n = 1)
is methane (CH4) and the second (n = 2) is ethane (C2H6). Both are gases
at room temperature and pressure. This general formula can be used to
work out the formula of any other alkane if we know the number of carbon
atoms it consists of. The following table gives the molecular formula
and name of the first few alkanes, plus an indication of some of their
physical properties.
members of this group of hydrocarbons are distinguished by possessing
the general molecular formula Cn H2n+2, where is 1, 2, 3, etc., for
successive members of the group. The first member of the series (n = 1)
is methane (CH4) and the second (n = 2) is ethane (C2H6). Both are gases
at room temperature and pressure. This general formula can be used to
work out the formula of any other alkane if we know the number of carbon
atoms it consists of. The following table gives the molecular formula
and name of the first few alkanes, plus an indication of some of their
physical properties.
Table 2.2 Formulae and physical properties of some alkanes
| name | Molecular formula | Melting point (oC) | Boiling point (oC) | Density (gcm–3) |
| Methane | CH4 | –183 | –162 | gas |
| Ethane | C2H6 | –172 | –89 | gas |
| Propane | C3H8 | –188 | –42 | gas |
| Butane | C4H10 | –135 | –1 | gas |
| Pentane | C5H12 | –130 | 36 | 0.626 |
| Hexane | C6H14 | –95 | 69 | 0.659 |
| Heptane | C7H16 | –91 | 98 | 0.684 |
| Octane | C8H18 | –57 | 126 | 0.703 |
| Nonane | C9H20 | –54 | 151 | 0.718 |
| Decane | C10H22 | –30 | 174 | 0.730 |
Structure of alkanes
In
the alkanes, all carbon atoms show a covalency of four. Table 2.3 shows
the structures of the first five members of the alkanes.
the alkanes, all carbon atoms show a covalency of four. Table 2.3 shows
the structures of the first five members of the alkanes.
The Homologous Series of the Three Families of Hydrocarbons
Write the homologous series of the three families of hydrocarbons
A
homologous series is a series of compounds with similar chemical
properties which differ by –CH2. Such series has the following
characteristics:
homologous series is a series of compounds with similar chemical
properties which differ by –CH2. Such series has the following
characteristics:
- All members obey the general molecular formula, e.g. for alkanes Cn H2n+2, alkenes Cn H2n and alkynes, Cn H2n-2.
- Each member differs, in molecular formula, from the next by CH2, e.g. alkanes are CH4, C2H6, C3H8, and so on.
- All members show similar chemical properties.
- The
general properties of members change gradually in the same direction
along the series, e.g. in alkanes, boiling points and freezing points
rise with increase in the number of carbon atoms (CH4 – a gas; C5H12 – a
liquid; C20H42 – a solid at ordinary temperatures and pressure). - General
methods of preparation are known which can be applied to any member of
the series. Other homologous series are alcohols, CnH2n+1 and carboxylic
acids, CnH2n+1COOH.
Nomenclature of alkanes
The
term nomenclature means naming. Organic compounds are named using IUPAC
system of nomenclature. IUPAC stands for International Union of Pure
and Applied Chemistry.
term nomenclature means naming. Organic compounds are named using IUPAC
system of nomenclature. IUPAC stands for International Union of Pure
and Applied Chemistry.
Rules of Nomenclature
1. Name the longest unbranched carbon chain. For example, consider the following compound:
In this compound, the longest unbranched chain is
The longest chain is, therefore, butane.
2. Name the functional groups. Functional groups are branches of the main carbon chain. These are sometimes called alkyl groups.
Examples of alkyl groups are as follows:
- CH3 – methyl
- CH3CH2 – ethyl
- CH3CH2CH2 – propyl
- Cl – chloro
- Br – bromo
- I – iodo
- F – flouro
3. Give the position(s) of the functional group(s) using lower numbers when possible. Consider the following example:
There are two possibilities of naming the above compound but only one is correct.
- 2 – methylbutane
- 3 – methylbutane
The first name is correct because it bears the lowest number (2). The second name is wrong because it bears a large number (3).
4. Names of the functional groups are named in alphabetical order in the final name.
Example
Consider the following compound:
The name of the compound is: 3–bromo–2–choloropentane
Note: We start with bromo and not chloro because b comes before c in alphabet (a, b, c, d …)
5.
If there are identical functional groups, use the prefixes di (2), tri
(3), tetra (4), penta (5), etc. These prefixes do not account for
alphabetical order.
If there are identical functional groups, use the prefixes di (2), tri
(3), tetra (4), penta (5), etc. These prefixes do not account for
alphabetical order.
Examples:
6. Commas separate numbers and hyphens separate numbers from words.
The Concept of Isomerism
Explain the concept of isomerism
Isomers are organic compounds with the same molecular formula but different structural formulae.
Isomerism
is the occurrence of two or more compounds with the same molecular
formula but different molecular structures (structural formulae).
is the occurrence of two or more compounds with the same molecular
formula but different molecular structures (structural formulae).
Isomers of the same molecular formula have different physical and chemical properties because of structural differences.
Structural Formulae of all Isomers of Hydrocarbons up to Five Carbon Atoms
Write structural formulae of all isomers of hydrocarbons up to five carbon atoms
Example 1
1.
Butane The two isomers of butane, with molecular formula C4H10, are as
shown below. Isomers can be presented either in an open formula
(structure) as follows.
Butane The two isomers of butane, with molecular formula C4H10, are as
shown below. Isomers can be presented either in an open formula
(structure) as follows.
Example 2
Pentane
The three isomers of pentane showa open formula asfollows:
Isomers of Hydrocarbons up to Five Carbon Atoms
Name the isomers of hydrocarbons up to five carbon atoms
Example 3
alkanes showing isomerism
1.
Butane The two isomers of butane, with molecular formula C4H10, are as
shown below. Isomers can be presented either in an open or condensed
formula (structure).
Butane The two isomers of butane, with molecular formula C4H10, are as
shown below. Isomers can be presented either in an open or condensed
formula (structure).
Note:
Remember that CH4, C2H6 and C3H8 have no isomers because they cannot
form alkyl groups, that is, they cannot be branched. Isomerism in
alkanes starts from an alkane with four carbon atoms (butane) in its
structure (C4H10).
Remember that CH4, C2H6 and C3H8 have no isomers because they cannot
form alkyl groups, that is, they cannot be branched. Isomerism in
alkanes starts from an alkane with four carbon atoms (butane) in its
structure (C4H10).
2. Pentane
The three isomers of pentane are shown as follows:
Alkenes
Alkanes
are members of a homologous series of hydrocarbons with general
molecular formula Cn H2n where n = 2, 3, 4, etc. The common structural
feature is the presence of a carbon–carbon double bond:
are members of a homologous series of hydrocarbons with general
molecular formula Cn H2n where n = 2, 3, 4, etc. The common structural
feature is the presence of a carbon–carbon double bond:
There
is no member of this series for n = 1 since there needs to be at least
two carbon atoms present to have a double bond. Table 2.3 shows the
first five members of alkenes.
is no member of this series for n = 1 since there needs to be at least
two carbon atoms present to have a double bond. Table 2.3 shows the
first five members of alkenes.
Structure of alkenes
Alkanes
are characterized by possessing one or more carbon to carbon double
bond(s) (C=C) in the carbon chain. Alkenes are unsaturated hydrocarbons
because it is possible to break the double bond and add extra atoms to
the parent molecule.
are characterized by possessing one or more carbon to carbon double
bond(s) (C=C) in the carbon chain. Alkenes are unsaturated hydrocarbons
because it is possible to break the double bond and add extra atoms to
the parent molecule.
Table 2.4 shows the structures of the first five members of the homologous series of alkenes.
Nomenclature of alkenes
Rules for naming alkenes
- Names of alkenes have the ending –ene.
- The double bond is given the number of the carbon atom where it begins.
- In
addition to the rules discussed earlier, the position of the double
bond must be included in the name .Examples: CH3–CH=CH3 prop-1-ene ,
CH3–CH=CH–CH3 but-2-ene - Double bonds are given the lowest number possible, usually lower than the functional groups.
Counting
from the left to right, the double bond (=) is on carbon number 4 and
from the right to left, it is on carbon number 3. Because the double
bonds should be given the lowest umber possible, the name of the
compound is, therefore, hept-3-ene instead of hept-4-ene.
from the left to right, the double bond (=) is on carbon number 4 and
from the right to left, it is on carbon number 3. Because the double
bonds should be given the lowest umber possible, the name of the
compound is, therefore, hept-3-ene instead of hept-4-ene.
Isomerism
Alkenes,
like alkanes show branching isomerism, for exampleCH3–CH=CH–CH3
(pent-1-ene) can be branched into (3-methylbut-1-ene) as follows:
like alkanes show branching isomerism, for exampleCH3–CH=CH–CH3
(pent-1-ene) can be branched into (3-methylbut-1-ene) as follows:
They
also show positional isomerism due to different positions of the double
bond in the molecule, for example, pent-1-ene and pent-2-ene are both
the isomers of pentene (C5H10):
also show positional isomerism due to different positions of the double
bond in the molecule, for example, pent-1-ene and pent-2-ene are both
the isomers of pentene (C5H10):
CH2=CH–CH2–CH2–CH3 pent-1-ene
CH3–CH=CH–CH2–CH3 pent-2-ene
Other examples include:
Alkynes
These
are homologous series of hydrocarbons with the general formula CnH2n-2.
The common structural feature is the presence of a carbon-carbon triple
bond (CC). There is no member for n = 1 because, as for the alkenes,
there needs to be at least two carbonatoms present to have a triple
bond. Table 2.5 shows the first five members of the alkynes.
are homologous series of hydrocarbons with the general formula CnH2n-2.
The common structural feature is the presence of a carbon-carbon triple
bond (CC). There is no member for n = 1 because, as for the alkenes,
there needs to be at least two carbonatoms present to have a triple
bond. Table 2.5 shows the first five members of the alkynes.
Nomenclature of alkynes
Rules for naming alkynes
- Alkynes have the ending –yne
- Triple bond is given the lowest number possible, usually lower than the functional groups.
- As for the alkenes the position of the triple bond must be included in the name.
Isomerism
Alkynes
show branching isomerism and positional isomerism. The alkyne with the
molecular formula, C5H8, shows chain branching isomerism, for instance,
show branching isomerism and positional isomerism. The alkyne with the
molecular formula, C5H8, shows chain branching isomerism, for instance,
A General Formula to Identify the Families of Hydrocarbons
Apply a general formula to identify the families of hydrocarbons
Activity 1
Apply a general formula to identify the families of hydrocarbons
Properties of Hydrocarbons
The Physical Properties of Lower Hydrocarbons; Alkanes, Alkenes and Alkynes
Explain the physical properties of lower hydrocarbons; alkanes, alkenes and alkynes
Alkanes
- The first four alkanes are gases at room temperature, the next twelve (C5–C17) are liquids, and the rest are solids.
- The
boiling and melting points of unbranched alkanes increase as the molar
masses increase. The larger the molecule, the higher the boiling point
or melting point. - Branched alkanes have lower boiling points than the unbranched alkanes,
- Alkanes are very sparingly soluble in water but they easily dissolve in organic solvents.
- In an alkane molecule, each carbon atom forms four single covalent bonds. This means that alkanes are saturated hydrocarbons.
Alkenes
Here again we find that alkenes posses physical properties that arethe same as those of alkanes, i.e.
- They are insoluble in water but soluble in organic solvents suchas benzene, ether and chloroform.
- They are less dense than water.
- The boiling point increases with increase in molecular weighti.e., increase in the number of carbon atoms.
Alkynes
The physical properties of the alkynes are essentially the same as those of the alkanes and alkenes.
The Concept of Saturated and Unsaturated Hydrocarbons
Explain the concept of saturated and unsaturated hydrocarbons
Hydrocarbons
are classified into two distinct categories: saturated and unsaturated.
Saturated hydrocarbons contain only one carbon-carbon single bond.
Unsaturated hydrocarbons contain at least one carbon-carbon double or
triple bond. The unsaturated hydrocarbons are more reactive and they
contain fewer hydrogen atoms bonded to the carbon atoms than saturated
hydrocarbons.
are classified into two distinct categories: saturated and unsaturated.
Saturated hydrocarbons contain only one carbon-carbon single bond.
Unsaturated hydrocarbons contain at least one carbon-carbon double or
triple bond. The unsaturated hydrocarbons are more reactive and they
contain fewer hydrogen atoms bonded to the carbon atoms than saturated
hydrocarbons.
The Chemical Properties of Alkanes, Alkenes and Alkynes
Compare the chemical properties of alkanes, alkenes and alkynes
Alkanes
Alkanes are not as reactive as other hydrocarbons. However, they exhibit the following chemical properties:
Combustion: alkanes burn in a sufficient amount of air to form carbon dioxide and steam.
Cracking: this is a process in which large alkanes are broken down into smaller hydrocarbons.
Halogenation:
under special conditions (sunlight or 300°C), halogens react with
alkanes in a substitution reaction. A substitution reaction is a
reaction in which one atom or group of atoms replaces another.
under special conditions (sunlight or 300°C), halogens react with
alkanes in a substitution reaction. A substitution reaction is a
reaction in which one atom or group of atoms replaces another.
Alkenes
Alkenes
are much more reactive than alkanes. This is because thedouble bond can
break to form single bonds and add on otheratoms. Because the double
bond allows them to add on moreatoms, alkenes are said to be
unsaturated. The alkanes don‟t havedouble bonds and can‟t add on more
atoms, so they are saturated.
are much more reactive than alkanes. This is because thedouble bond can
break to form single bonds and add on otheratoms. Because the double
bond allows them to add on moreatoms, alkenes are said to be
unsaturated. The alkanes don‟t havedouble bonds and can‟t add on more
atoms, so they are saturated.
Combustion: alkenes burn in sufficient supply of air (explodes)to form carbon dioxide and steam.
Addition
reactions: Alkenes give a number of addition reactions in which two
hydrogen atoms (or their equivalent) are taken intocombination per
molecule to form a single product. The following are some of the
addition reactions shown by alkenes:
reactions: Alkenes give a number of addition reactions in which two
hydrogen atoms (or their equivalent) are taken intocombination per
molecule to form a single product. The following are some of the
addition reactions shown by alkenes:
Alkynes
Addition: having carbon–carbon trip bonds, alkynes are unsaturated compounds. They give a number of addition reactions:
With
acidified potassium manganate (VII) solution: At room temperature, with
shaking, ethyne quickly decolourizes this solution (i.e. reduces it)
with formation of ethanedioc acid
acidified potassium manganate (VII) solution: At room temperature, with
shaking, ethyne quickly decolourizes this solution (i.e. reduces it)
with formation of ethanedioc acid
Polymerization
Combustion:
Salt formation:
This
is a test for terminal alkynes, i.e. those with C≡C at the end. For
those with C≡C at the centre, no reactions take place e.g.
CH3–CH2–C≡C—CH2–CH3 + AgNO3→ No reaction!
is a test for terminal alkynes, i.e. those with C≡C at the end. For
those with C≡C at the centre, no reactions take place e.g.
CH3–CH2–C≡C—CH2–CH3 + AgNO3→ No reaction!
Alcohols
Alcohols
form a homologous series of general molecular formula, CnH2n+2, where n
= 1, 2, 3, etc. for successive members of the group. The hydroxyl
group, OH, is the characteristic functional group of the alcohols.
form a homologous series of general molecular formula, CnH2n+2, where n
= 1, 2, 3, etc. for successive members of the group. The hydroxyl
group, OH, is the characteristic functional group of the alcohols.
Preparation of Ethanol in the Laboratory
Prepare ethanol in the laboratory
Laboratory
preparation of an alcohol involves heating a haloalkane with an aqueous
alkali. Ethanol is prepared by heating a mixture of bromoethane and
sodium hydroxide solution. The reaction proceeds as follows:
preparation of an alcohol involves heating a haloalkane with an aqueous
alkali. Ethanol is prepared by heating a mixture of bromoethane and
sodium hydroxide solution. The reaction proceeds as follows:
The ethanol, as indicated in the equation will be in solution. It canbe isolated by distillation.
Ethanol
can also be prepared by fermentation of glucose wherebyyeast produces
an enzyme called zymase which acts as an organiccatalyst to catalyse the
degradation of glucose.
can also be prepared by fermentation of glucose wherebyyeast produces
an enzyme called zymase which acts as an organiccatalyst to catalyse the
degradation of glucose.
For
substantial fermentation to take place, a mixture of glucose and yeast
is left in a warm place for a considerable length of time.
substantial fermentation to take place, a mixture of glucose and yeast
is left in a warm place for a considerable length of time.
The equation for the reaction taking place is:
The Homology of Alcohols up to Five Carbon Atoms
Write the homology of alcohols up to five carbon atoms
Alcohols
are named as if they are derived from alkanes by the replacement of
hydrogen atom by the hydroxyl group (–OH). The lowest two members
containing one and two carbon atoms in the molecule, are, respectively,
methanol and ethanol. Their structural formulae are shown below:
are named as if they are derived from alkanes by the replacement of
hydrogen atom by the hydroxyl group (–OH). The lowest two members
containing one and two carbon atoms in the molecule, are, respectively,
methanol and ethanol. Their structural formulae are shown below:
Other members of the series are as shown below:
| Number of carbons per molecule (n) | Name | Formula |
| 1 | Methanol | CH3OH |
| 2 | Ethanol | C2H5OH |
| 3 | Propanol | C3H7OH |
| 4 | Butanol | C4H9OH |
| 5 | Pentanol | C5H11OH |
| 6 | Hexanol | C6H13OH |
| 7 | Heptanol | C7H15OH |
| 8 | Octanol | C8H17OH |
| 9 | Nonanol | C9H19OH |
| 10 | Decanol | C10H21OH |
The successive members of the series have molecular formulae which differ by CH2.
Like
other series, alcohols exhibit isomerism. For instance, propanol
(C3H7OH) can have two different structural formulae as exemplified
below:
other series, alcohols exhibit isomerism. For instance, propanol
(C3H7OH) can have two different structural formulae as exemplified
below:
The first is called propan-1-ol because the OH group is on the first carbon atom.
The second is called propan-2-ol because the OH group is on the second carbon atom.
Structure of all Isomers of Saturated Alcohols up to Five Carbon Atoms
Write structure of all isomers of saturated alcohols up to five carbon atoms
Nomenclature of branched alcohols
Rules:
- For branched alcohols, the–OH group is given the lowest number than the alkyl group.
- The
alcohol group (–OH) or the alkyl groups can be attached to different
positions of the carbon chain. It is the different positions of these
groups that result to the different names of the alcohol. - The carbon chain may have several branches of different alkyl groups.
Examples:
Note: Both the methyl (–CH3) and hydroxyl (–OH) groups are on carbon number 2. The longest unbranched carbon chain is
Isomers of Alcohols up to Five Carbon Atoms
Name all isomers of alcohols up to five carbon atoms
Alcohols
exhibit chain branching isomerism as with all the other homologous
series. In addition, they show an isomerism based on the position of the
hydroxyl group (–OH) in the molecule.
exhibit chain branching isomerism as with all the other homologous
series. In addition, they show an isomerism based on the position of the
hydroxyl group (–OH) in the molecule.
Alcohols
that have the formula CH3OH and CH3CH2OH have only one possible
structure. They do not have isomers. The –OH group in ethanol, CH3CH2OH,
is always on the last carbon atom.
that have the formula CH3OH and CH3CH2OH have only one possible
structure. They do not have isomers. The –OH group in ethanol, CH3CH2OH,
is always on the last carbon atom.
With
the formula CH3CH2CH2OH, however, the –OH group can either be attached
to the first or second carbon of the carbon chain to give two isomers
namely, CH3CH2CH2OH (propan-1-ol) and
the formula CH3CH2CH2OH, however, the –OH group can either be attached
to the first or second carbon of the carbon chain to give two isomers
namely, CH3CH2CH2OH (propan-1-ol) and
Isomers of other members in the series are as follows:
Butanol: C4H9OH or CH3CH2CH2CH2OH
Isomers:
Pentanol: C5H11OH or CH3CH2CH2CH2CH2OH
ItsIsomers:
The Properties of Alcohol
Describe the properties of alcohol
Ethanol
is the best known and most important of all alcohols. It has several
different uses. Due to its diverse use, its name is used interchangeably
with that of “alcohol” as if it represents all other classes of
alcohols.
is the best known and most important of all alcohols. It has several
different uses. Due to its diverse use, its name is used interchangeably
with that of “alcohol” as if it represents all other classes of
alcohols.
Physical properties of ethanol (alcohol)
- It is a clear, colourless liquid with a boiling point of 78°C.
- It is readily soluble in water and it mixes completely with it (miscible).
- It evaporates very easily when exposed to air (it is a very volatile liquid).
Chemical properties of ethanol
Reaction with oxygen (combustion)
It burns well in oxygen giving carbon dioxide and water, and plenty of heat.
This reaction is the basis of its use as a fuel.
Reaction with sodium metal
Ethanol
reacts vigorously with sodium to produce sodium ethoxide and hydrogen.
However, the reaction is not as vigorous as the reaction between sodium
and water.
reacts vigorously with sodium to produce sodium ethoxide and hydrogen.
However, the reaction is not as vigorous as the reaction between sodium
and water.
Methanol reacts similarly to produce sodium methoxide and hydrogen:
Reaction with ethanoic acid (esterification)
Alcohols react with organic acids to form sweet-smelling oily liquids known as esters.
The
symbol, H+, indicates that the reaction takes place in acidified
conditions. Normally dilute sulphuric acid is added as a catalyst for
this esterification reaction.
symbol, H+, indicates that the reaction takes place in acidified
conditions. Normally dilute sulphuric acid is added as a catalyst for
this esterification reaction.
Reaction with concentrated sulphuric acid
Concentrated sulphuric acid dehydrates ethanol to give ethene. The reaction takes place at 180°C.
Reaction with phosphorus pentachloride
Ethanol reacts vigorously with phosphorus pentachloride to give chloroethane, phosphorus oxychloride and hydrogen chloride.
Hydrogen chloride is evolved as white fumes, and this reaction is used to test for alcohols and other hydroxyl compounds.
Oxidation
Ethanol
is oxidized by strong oxidizing agents such as warm acidified potassium
dichromate or acidified potassium permanganate to ethanoic acid.
is oxidized by strong oxidizing agents such as warm acidified potassium
dichromate or acidified potassium permanganate to ethanoic acid.
The Uses of Alcohol
Explain the uses of alcohol
Alcohol
is used as an alcoholic beverage. Different alcohol drinks contain
different amounts of ethanol. Beer and wines contain 8–13% of ethanol.
Sprits such as whisky, gin, brandy, rum, etc. contain about 35–40% of
ethanol. However, these beverages must only be drunk with moderation as
too much consumption of alcohol can lead to heath problems.
is used as an alcoholic beverage. Different alcohol drinks contain
different amounts of ethanol. Beer and wines contain 8–13% of ethanol.
Sprits such as whisky, gin, brandy, rum, etc. contain about 35–40% of
ethanol. However, these beverages must only be drunk with moderation as
too much consumption of alcohol can lead to heath problems.
Ethanol as fuel.
- Ethanol
burns with a clear flame, giving out quite a lot of heat.C2H5OH(l) +
3O2(g) → 2CO2(g) + 3H2O(g) + heat On a small scale, ethanol can be used
as methylated spirit (ethanol mixed with methanol or other compounds) in
spirit lamps and stoves. - Ethanol produced by fermentation of
sugar from sugar cane has been used as an alternative fuel to gasoline
(petrol), or mixed with gasoline to produce “gasohol”.
Ethanol as a solvent.
Alcohol
is a good solvent, dissolving many compounds that are insoluble in
water. The fact that it evaporates easily makes it a good solvent in
products like glues, paints, varnishes, deodorants (perfumes), and
aftershaves.
is a good solvent, dissolving many compounds that are insoluble in
water. The fact that it evaporates easily makes it a good solvent in
products like glues, paints, varnishes, deodorants (perfumes), and
aftershaves.
It is used in the manufacture of many chemicals
For
example, it is used in making sweet–smelling liquids called esters
which are used as solvents, in food flavourings, and as fragrance in
beauty products (cosmetics).
example, it is used in making sweet–smelling liquids called esters
which are used as solvents, in food flavourings, and as fragrance in
beauty products (cosmetics).
Ethanol
is also used as an ingredient in iodine tincture (a mixture of alcohol
and iodine) which is largely used in hospitals for treatment of wounds.
is also used as an ingredient in iodine tincture (a mixture of alcohol
and iodine) which is largely used in hospitals for treatment of wounds.
The Harmful Effects of Alcohol
Explain the harmful effects of alcohols
In
spite of its widest use as a useful product, ethanol, taken as an
alcoholic beverage, has a lot of detrimental health effects. Some of the
effects of alcohol are as follows:
spite of its widest use as a useful product, ethanol, taken as an
alcoholic beverage, has a lot of detrimental health effects. Some of the
effects of alcohol are as follows:
- Even
just one drink impairs coordination and judgement. It is a factor among
the many causes of road accident as it leads to blurred vision. - It
leads to lack of muscular control (e.g. drunken stagger) and ultimately
to coma, the state in which a person is said to be dead–drunk. - Prolonged
consumption of too much alcohol causes liver deterioration (cirrhosis
of the liver) which can cause liver failure and death. Also heavy
drinking eventually damages the muscle tissue of the heart. There may
well be some long–term damage to the brain. All these health effects
accelerate death. - Alcohol is a depressive drug and can be
addictive. Occasional drinking may lead to alcohol addiction, a
condition during which a person is said to be alcoholic. When a drunkard
finds him/herself in such a condition it is very difficult to go
without drinking. This can eventually lead to poverty as a drunkard
spends most of his/her time and money drinking (buzzing). - Alcohol can make someone aggressive. This accounts for many arrests, conviction and jail sentences.
- Excessive drinking causes depression and other mental disorders.
- It
can lead to gastric ulcers, high blood pressure and cancer of the
mouth, throat, and gullet. People who smoke as well are at greater risk
from thesecancers.
Women
are at greater risk than men from the harmful effects of alcohol. One
reason is that men‟s bodies have higher water content. So alcohol in
their body fluids is more diluted.
are at greater risk than men from the harmful effects of alcohol. One
reason is that men‟s bodies have higher water content. So alcohol in
their body fluids is more diluted.
Drinking during pregnancy can damage the baby‟s brain and heart, and slow down its growth so that it is born underweight.
Carboxylic
acids form a homologous series of the general formula CnH2n+1COOH (or
CnH2n+1CO2H), where n = 1, 2, 4, etc. for successive members of the
group. All these acids have the characteristic functional (carboxyl)
group, –COOH, attached to a hydrocarbon chain.
acids form a homologous series of the general formula CnH2n+1COOH (or
CnH2n+1CO2H), where n = 1, 2, 4, etc. for successive members of the
group. All these acids have the characteristic functional (carboxyl)
group, –COOH, attached to a hydrocarbon chain.
Natural Sources of Organic Acids
Identify natural sources of organic acids
There are various natural sources of organic acids. Some of these sources are:
- milk (lactic acid)
- citrus fruits (citric acid);
- tobacco (nicotinic acid); and
- tea (tartaric acid).
The Oxidation of Ethanol to Ethanoic Acid
Explain the oxidation of ethanol to ethanoic acid
When exposed to open air, ethanol is oxidized (by oxygen of the air) to ethanoic acid. The reaction for the process occurs thus:
The Structures of the Homologues of Carboxylic Acids up to Five Carbon Atoms
Write the structures of the homologues of carboxylic acids up to five carbon atoms
Carboxylic
acids are named as if they are derived from alkanes by the replacement
of one hydrogen atom by the –COOH group. The two lowest members,
containing one atom and two carbon atoms respectively, are:
acids are named as if they are derived from alkanes by the replacement
of one hydrogen atom by the –COOH group. The two lowest members,
containing one atom and two carbon atoms respectively, are:
The other members of the homologous series are as shown below:
The
successive members of the series have molecular formulae which differ
by –CH2 It is important to remember that every carboxylic acid molecule
contains the functional group –COOH which is called the carboxyl group.
successive members of the series have molecular formulae which differ
by –CH2 It is important to remember that every carboxylic acid molecule
contains the functional group –COOH which is called the carboxyl group.
The Isomers of Carboxylic Acids up to Five Carbon Atoms
Name the isomers of carboxylic acids up to five carbon atoms
Like
other organic compounds, carboxylic acids also exhibit isomerism.
Isomers of carboxylic acid are a result of branching of the hydrocarbon
end (R) rather than the position of the carboxyl group in a molecule of
the carboxylic acid. More isomers of the carboxylic acids can be created
by branching the hydrocarbon end in as many different ways as possible.
other organic compounds, carboxylic acids also exhibit isomerism.
Isomers of carboxylic acid are a result of branching of the hydrocarbon
end (R) rather than the position of the carboxyl group in a molecule of
the carboxylic acid. More isomers of the carboxylic acids can be created
by branching the hydrocarbon end in as many different ways as possible.
Rules
The carbon of the carboxyl group (–COOH) is considered as carbon atom number 1.
Identify the positions of the alkyl group(s) attached to the (longest) acid chain. For example, in a molecule,
the alkyl group is methyl (–CH3) and it is attached to carbon number 2.
Name
the branched alkyl group, followed by the name of the acid to which the
alkyl group is attached. For example, in the case above (rule no.2):
the branched alkyl group, followed by the name of the acid to which the
alkyl group is attached. For example, in the case above (rule no.2):
- the alkyl group is methyl;
- it is attached to carbon number and
- the acid to which it is attached is butanoic acid,CH3CH2CH2COOH
Therefore, the name of the compound is 2-methylbutanoic acid.
In
case there occurs more than one alkyl groups in the compound the
prefixes di(2), tri(3), tetra(4) etc (as it was the case in alkanes) may
be used. For, example in the compound
case there occurs more than one alkyl groups in the compound the
prefixes di(2), tri(3), tetra(4) etc (as it was the case in alkanes) may
be used. For, example in the compound
- there are two methyl groups, one attached to carbon number 2 and the other to carbon number 3; and
- they are both attached to butanoic acid chain.
Therefore, the name of the compound is 2,3-dimethylbutanoic acid.
Isomerism and nomenclature
Branching
isomerism is found in this homologous series. Isomerism in carboxylic
acids begins from butanoic acid, C3H7COOH. The first three members of
the series do not show isomerism because their hydrocarbon ends do not
form branches. The following are the structures and names of the isomers
of carboxylic acids up to five carbon atoms:
isomerism is found in this homologous series. Isomerism in carboxylic
acids begins from butanoic acid, C3H7COOH. The first three members of
the series do not show isomerism because their hydrocarbon ends do not
form branches. The following are the structures and names of the isomers
of carboxylic acids up to five carbon atoms:
- Butanoic acid, C3H7COOH or C3H7CO2H or CH3CH2CH2COOH
Isomers:
- Pentanoic acid, C4H9COOH
Isomers
The Properties of Carboxylic Acids
Explain the properties of carboxylic acids
Carboxylic acids are weak acids. They are slightly ionized in dilute solutions.
Like
inorganic acids, their solutions contain H+ ions. The presence of H+
ions give the solutions acidic behaviour, that is, their solutions
affect indicators, just like the inorganic acids do.
inorganic acids, their solutions contain H+ ions. The presence of H+
ions give the solutions acidic behaviour, that is, their solutions
affect indicators, just like the inorganic acids do.
Neutralization
Like
inorganic acids, carboxylic acids react with metals, alkalis,
carbonates, and hydrogen carbonates to form salts. For example:
inorganic acids, carboxylic acids react with metals, alkalis,
carbonates, and hydrogen carbonates to form salts. For example:
Esterification
The
reaction between carboxylic acids and alcohols is called
esterification. The acids will react reversibly with alcohols to form
sweet–smelling esters. Concentrated sulphuric acid is a catalyst for the
reaction.
reaction between carboxylic acids and alcohols is called
esterification. The acids will react reversibly with alcohols to form
sweet–smelling esters. Concentrated sulphuric acid is a catalyst for the
reaction.
The
reaction can be reversed to recover an acid and alcohol again by
boiling the products (an ester + water) with a mineral acid (HCl or
H2SO4) or with an aqueous alkali (KOH or NaOH) as a catalyst.
reaction can be reversed to recover an acid and alcohol again by
boiling the products (an ester + water) with a mineral acid (HCl or
H2SO4) or with an aqueous alkali (KOH or NaOH) as a catalyst.
Esters
are manufactured for use as solvents, food flavourings, and fragrance
for perfumes and beauty products. Ethyl ethanoate is just one example of
many esters. The esters usually have strong and pleasant smells. Many
of these compounds occur naturally. They are responsible for the
flavours in fruits and for the scents of flowers. Fats and oils are
naturally occurring esters used for energy storage in plants and
animals. Some of the naturally occurring esters include:
are manufactured for use as solvents, food flavourings, and fragrance
for perfumes and beauty products. Ethyl ethanoate is just one example of
many esters. The esters usually have strong and pleasant smells. Many
of these compounds occur naturally. They are responsible for the
flavours in fruits and for the scents of flowers. Fats and oils are
naturally occurring esters used for energy storage in plants and
animals. Some of the naturally occurring esters include:
- vegetable oils e.g. palm oil, groundnut oil, cashewnut oil, olive oil, sunflower oil, etc; and
- animal fats.
All esters contain the functional group,
, where R is any alkyl group.
Preparation of Soap from Animal Fats or Vegetable Oil
Prepare soap from animal fats or vegetable oil
Vegetable
oils are formed from fatty acids and an alcohol called glycerol (also
called glycerine). Fatty acids are carboxylic acids with long chains of
carbon atoms. They are called “fatty” because the long chains repel
water, making them immiscible with water. Glycerol or glycerine (or
propane–1,2,3-triol) has three –OH groups. This is how fatty acids and
glycerol react:
oils are formed from fatty acids and an alcohol called glycerol (also
called glycerine). Fatty acids are carboxylic acids with long chains of
carbon atoms. They are called “fatty” because the long chains repel
water, making them immiscible with water. Glycerol or glycerine (or
propane–1,2,3-triol) has three –OH groups. This is how fatty acids and
glycerol react:
Preparation of soap from oils
Soap
is made by heating animal fats or vegetable oils with sodium hydroxide
solution. The oils react with the solution of sodium hydroxide and break
down to form glycerol and the sodium salts of their fatty acids. These
salts are used as soap. The reaction equation is:
is made by heating animal fats or vegetable oils with sodium hydroxide
solution. The oils react with the solution of sodium hydroxide and break
down to form glycerol and the sodium salts of their fatty acids. These
salts are used as soap. The reaction equation is:
This
process is known as saponification. The soap you buy is made from a
blend of different oils. When soap dissolves in water it ionizes thus:
process is known as saponification. The soap you buy is made from a
blend of different oils. When soap dissolves in water it ionizes thus:
The cleansing agent in soap is the ion, RCOO–
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