ORGANIC CHEMISTRY Notes
ORGANIC CHEMISTRY Notes
ORGANIC CHEMISTRY Notes
Amino acids, simple sugar molecules and even fats are carbon-containing compounds. Carbon is
therefore unique in the variety of compounds it can form. The peak of these compounds is the DNA
(deoxyribonucleic acid), the molecule that makes life possible.
The chemistry of these compounds is a separate branch of chemistry known as organic chemistry.
So, by definition:
All carbon compounds are organic except for a few inorganic compounds like oxides of carbon,
carbonate of metal ions.
There are over 6 millions organic compounds, these include hydrocarbon and others.
Carbon atoms can join to each other to form long chains. Atoms of other elements
can then attach to the chain.
The carbon atoms in the chain can be linked by single, double or triple covalent
bonds.
Carbon atoms can also arrange themselves in rings.
HYDROCARBON
Hydrocarbons are compounds which contain only the elements carbon and hydrogen covalently
bonded together. Examples are alkanes and alkenes.
In organic chemistry, the structure of a molecule is very important. It shows the bonds between
atoms. And as the length of the hydrocarbon chain increases, the strength of the weak forces
(intermolecular forces or van der Waal’s forces) is increased.
Homologous Series
Homologous series is a family of similar compounds with similar chemical properties due to the
presence of the same functional group.
A homologous series is a group of compound of increasing carbon number, where one differs from
the next by a–CH2-unit. That is, each molecule increases by a –CH2- as the chain gets longer.
Alkanes, for instance, form a homologous series with the same general formula C nH2n+2.
ALKANES
Alkanes are saturated hydrocarbons which contain carbon-carbon (C-C) covalent single bond with a
general formula CnH2n+2.
Alkanes are saturated because the molecules have only single covalent bonds between carbon
atoms. In other words, since carbon has a valency of four, the bonds not used in making chain are
linked to hydrogen atoms. So, no further atom can be added to their molecules. For this reason,
alkanes are generally unreactive, except in term of burning.
Alkanes are hydrocarbons with general formula CnH2n+2, where n is the number of carbon
atoms present.
All members of alkanes have name ending with –ane.
The name of each member indicates the number of carbon atoms present in the compound.
The first-six members of the alkane family and their molecular formula are shown below.
Under normal condition (r.t.p.), alkanes with up to four carbon atoms are gases. Those with carbon
atoms between five and sixteen, which in short are called C 5 to C16, are liquids while those with 17
carbon atoms or more are solids.
Alkanes are generally unreactive i.e. they do not react with most chemicals as they are saturated
hydrocarbons, having only C-C single bond. They do however undergo
Alkanes burns in air (oxygen) to give carbon dioxide and water, e.g.
Halogenations of alkanes are the reaction of alkanes with members of halogen in the presence of
sunlight.
In this reaction, one or more atom of alkanes is replaced with one or more halogen atoms. For
instance, in the presence of sunlight, methane (alkanes) reacts with chlorine (halogen) to form
chloromethane and hydrogen chloride.
In the above reaction, one hydrogen atom of methane is substituted for by a chlorine atom.
CH 2 Cl 2 CHCl 3 CCl 4
Uses of Alkanes
(1) Methane known as natural gas is used for cooking as well as for heating.
(2) Propane and butane are sold as liquefied petroleum gas (LPG).
(3) Propane and butane are used in gas lighters when mixed together.
(4) Butane is used as portable camping stoves, blow torches and gas-lighter.
These are compounds with the same Molecular formula but different structural formulae e.g.
butane and 2-methyl-propane (branched hydrocarbon) have the formula C4H10 but are different
structurally.
Isomerism is essentially in petroleum industry. For example, car engines do not run smoothly on a
straight chain octane compound but is better when burning a branched chain isomer as in
trimethylpentane.
Also, unlike lead compounds in petrol which causes pollution to the environment, this reduces
pollution, although more costly.
ALKENES
The ability of a carbon to from double bond is what gives rise to alkenes.
Alkenes therefore form another homologous series of hydrocarbons containing a double covalent
bond between carbon atoms (C=C) somewhere in the chain.
Molecules that posses a double covalent bond or a C=C double bond are said to be unsaturated.
Alkenes therefore are unsaturated hydrocarbon, because it is possible to break one of the two
bonds to add extra atoms to the molecule. For this reason, alkenes, unlike alkanes, are reactive or
are more reactive than alkanes.
Because of the double bond between carbon atoms, there is no alkene with one carbon atom. The
simplest alkene therefore contains two carbons atoms (C=C) and is called ethene. Its bond is shown
below.
Alkenes form a homologous series of hydrocarbon with the general formula CnH2n, where n
is the number of carbon atoms.
All members of alkenes have name ending with –ene.
Each member of alkenes homologous series differ from the next by a –CH 2 unit. And the first-three
are gases.
Isomers
Like alkanes, alkenes also form isomers. In this, the position of the double bond is moved along the
chain.
The structures are different because of the position of the double bond. In but-1-ene, the double
bond is between carbon atoms 1 and 2, whereas in but-2-ene, it is between carbon atoms 2 and 3.
These two are straight-chain isomers.
Branched-chain Isomer
Manufacture of alkenes
Few alkenes occur in nature. Most alkenes used by the petrochemical industries are obtained from
a process known as catalytic cracking.
This is the breakdown of larger alkanes (the less useful alkane molecules) obtained from fractional
distillation of crude oil (petroleum) into alkenes and smaller alkanes.
The demand for the various fractions from the refinery does not necessarily match with their
supply. For lighter fractions such as gasoline (petrol), the demand is greater than supply. The
opposite is the case for heavier fractions such as kerosene (paraffin) and diesel. For this reason,
larger alkanes molecules (from these heavier fractions) are broken into smaller, more valuable
molecules by a process called catalytic cracking.
Petroleum or crude oil is mainly made up of a mixture of alkanes. Large alkanes are mostly solid
and are heavy and bulky. For this reason, they are less useful. They are therefore
cracked/breakdown to meet the demand for the small alkanes molecules that are required in large
amount.
This process takes place in a huge reactor. It involves passing the larger alkane molecules over a
catalyst of aluminium and chromium oxide heated to 5000C at a pressure of 12atm. The cracked
vapours containing smaller molecules are separated by distillation.
The shortened hydrocarbon molecules are produced by the following type of reaction:
C18H38 C18H36 + H2
(2) Dehydration of alcohol
Alkenes can also be prepared by dehydration of an alcohol by hot concentrated sulphuric acid. The
ethanol vapour is passed over a heated catalyst. The catalyst can be aluminium oxide or broken
pieces of porous pot. For example, to produce ethene, ethanol is dehydrated.
The double bond makes alkenes more reactive than alkanes during chemical reaction. Other
elements or molecules can be added across the double bonds of alkenes to make them saturated.
This process is known as addition reaction.
1. Addition reaction
Alkenes react with hydrogen in the presence of nickel or platinum catalyst at temperature between
1500C-3000C to form alkanes. It is therefore the addition of hydrogen across a C=C double bond of
al kene double bond. This process is called hydrogenation.
E.g. hydrogen when added across the double bond in alkene form alkanes.
diagram
Hydrogenation is used in the manufacture of margarine from vegetable oil. Vegetable oil is unstable
with many C=C double bonds. By the addition of hydrogen some, but not all, of the C=C double
bonds, the liquid vegetable oil. Can be made into solid but spreadable fat (margarine).
The vegetable oils of interest include corn oil and sunflower oil. They are edible oils and contain
long chain organic acids (fatty acids). So, oils such as sunflower oil are rich in poly-unsaturated
molecule s. This means there melting point is relatively low and oil remains liquid at normal
temperature, even with refrigeration.
297
Animal fats tend to be more saturated than vegetable oils or fats. However, many doctors now
believe that unsaturated fats are healthier than saturated ones. This is why margarines are left
partially unsaturated. That is, not all C=C double bonds are hydrogenated
Hydrogenation can convert these molecules into margarine (saturated one), which can be spread
on the bread more easily than the liquid oil.
Alkenes react with steam to produce alcohol. Here, water is added across the double bond (C=C)
over a phosphoric acid catalyst at a temperature of 3000C and pressure of 60atm.
This is used as chemical test for unsaturated hydrocarbon. If an alkene, such as ethene, is
shaken/bubbled with a solution of bromine in water
If it is alkene such as ethene, a reaction takes place in which bromine atoms join to the
alkene double bond. This result in reddish (orange) brown bromine solution becoming
colourless.
Ethene + Bromine dibromo ethane
Diagram 292
The double bond in ethene breaks open and forms new bonds by the addition of bromine atoms.
If it is alkane such as methane, no colour change takes place. In order words, the solution
would remain reddish (orange)-brown. This indicates no reaction i.e. alkane would give no
reaction with the bromine water. This is because there are no double bonds between the
carbon atoms of alkanes.
Polymerisation is the joining of many small molecules of alkenes at high temperature of 2000C and
pressure of 2000 atm. to form a large molecule.
The small molecules joining together are known as monomers, while the large molecule formed is
called polymer.
Polymersare therefore large organic macromolecules that are made up of small repeating units
known as monomers joined together. These units are repeated any number of times from about a
hundred to more than a million.
Diagram 326
This reaction can be summarized by the equation:
Note: When drawing the structure of poly(ethene and other polymers, do not forget to put in the n
outside the bracket.
This process is called addition polymerisationbecause the monomers (ethenes) add up to form a
polymer (polyethene). This is made possible because ethene contain C=C double bonds which
enables many molecules of ethene to join to each other to form a large molecule..
Other alkene molecules can also produced addition polymers. Propene fro instance will polynerised
to produce poly(propene).
326
Note, the long chain molecule is similar in structure to poly(ethene) but with methyl (-CH 3)
attached to every other carbon atom in the chain
327
Polytetrafluoroethene (PTFE) produced from tetrafluoroethene.
2. Combustion reaction
Alkenes like alkanes, burns in oxygen to form carbon dioxide and water with a lot of heat, e.g.
Uses of alkenes
Alcohols are series of organic compounds with hydroxyl group (–OH) joined to a carbon atom in a
hydrocarbon chain. They form another homologous series with the general formula CnH2n+1OH. They
can otherwise be referred to as alkanols.
All members of alcohol family possess –OH as the functional group which is responsible for the
character reactions of the family or determines the characteristic reactions of the family.
265n
All members of alcohol have name ending with –ol. Below are the structure, name and formula of
the first-four members.
Methanol – CH3OH
Ethanol
Ethanol is the most important of the alcohols and is often called alcohol. It is one of the best-known
organic compounds.
Preparation of ethanol
(1) By Fermentation
Fermentation is a process whereby glucose in sugar or starchy food such as potatoes, grapes, cereal,
rice, barley etc. is broken down or turned into ethanol by natural catalyst called enzymes which are
present in yeast. The yeast ferment sugar to gain energy by anaerobic respiration.
As ethanol is toxic to yeast, fermentation is self-limiting. In the sense that once the ethanol
concentration has reached about 14%, or the sugar runs out, the multiplying yeast die and
fermentation ends. The best temperature for carring out fermentation is 37 0C .
Beer is made from barley, with hops and other ingredients added to produce distinctive
flavors. Beer contains about 4% by volume of ethanol.
Wine is made by fermenting grape juice. It contains between 8% and 14% by volume of
ethanol.
Stronger, more alcoholic, drinks are made in one of two ways. E.g. fortified wines such as
sherry and port, have pure ethanol added to them. Spirits, such as whisky, brandy and
vodka, are made by distillation.
Note, fermentation can be carried out in the laboratory using the apparatus below. It is called a
“laboratory fermentation vessel”.
266n
The air-lock allows gas to escape from the vessel but prevent airborne bacterial entering.
Addition of steam (water) to ethene done in the presence of phosphoric acid at 300 0C and 60 atm
produces ethanol. This is the industrial method of making ethanol.
Diagram
Comparing the methods of ethanol production
The two different method of producing ethanol have their respective advantages and
disadvantages. For instance,
The ethanol produced by fermentation comes from a renewable resource. It’s therefore
potentially “carbon neutral” when used as fuel. That is, the carbon dioxide released by
burning and during fermentation is balanced by that absorbed from the atmosphere by the
crop.
Properties of Ethanol
It is neutral;
It is colourless a liquid;
It is a volatile liquid;
It does not conduct electricity;
It has a boiling point of 780C;
It is readily soluble in water;
Reactions of Ethanol
Similar to alkanes and alkenes, alcohols undergo combustion reaction with oxygen to produce
carbon dioxide and water. Ethanol therefore burns with a clear flame giving out quite a lot of heat.
E.g.
Diagram
Vinegar therefore is a weak solution of ethanioc acid, previously called acetic acid. It is produced
commercially by biochemical oxidation using bacteria (Acetobacter).
This same oxidation can be achieved quickly by powerful oxidizing agents such as warm acidified
potassium manganate (VII). Its colours turn from purple to colourless.
(3) Ethanol can be dehydrated to produce ethene. Ethanol vapour is passed through over
heatedaluminium oxide or broken porous pot catalyst
(4) Esterification
Alcohols (ethanol) react with carboxylic acids (ethanoic acid) in the presence of concentrated
sulphuric acid to form sweet smelling oily liquid called ester (ethyl ethanoate). E.g. Ethanol reacts
with ethanioc acid to produce ethyl ethanoate.
Uses of Alcohol
(1) It is used as solvent. It dissolves many substances that are not soluble in water.
(2) It evaporates quickly, so it is used in paints, glues, vanishes, printing inks, deodorants, colognes
and after shaves.
(4) Methylated spirit is ethanol with small amounts of poisonous substance. This is used in spirit
(camping) stoves.
(5) Also some countries like Brazil are using ethanol (mixed with petrol) as fuel for cars.
For instance, ethanol can be used as methylated spirit (ethanol mixed with methanol or other
compounds) in spirit lamps and stoves.
Likewise, ethanol is a useful fuel that some countries have developed it as a fuel for cars. For
instance, Brazil who has a suitable climate for growing sugar cane started producing ethanol fuel in
1073.
Ethanol is produced by fermenting crop residues for this reason it is called a “biofuel.” And has been
used as alternative fuel in motor vehicles to fuel obtained from oil deposits. So, ethanol produced by
fermentation of sugar from sugar cane is used as an alternative fuel to gasoline (petrol) or mixed
with gasoline to produce “gasohol”.
Biofuels have the advantage of reducing the emission of carbon monoxide from cars. It therefore
reduces environmental damage. Nevertheless, overuse of biofuels could be harmful as it can lead to
more deforestation in order to grow biofuels crops such as sugar cane.,
Ethanol is the only alcohol that is safe to drink. The amount alcohol that a person may drink varies
with age, sex, weight and drinking history. However, ethanol must only be drunk moderately, if at
all. Because
Heavy drinking can cause a healthy liver to become fatty and enlarged. The eventual scar
(cirrhosis) can cause liver failure and death.
Prolonged heavy drinking can damage the tissue of the heart and some long-term damage
to the brain.
Alcohol is a depressive (weaken) drug and can be additive.
Drinking heavily on a particular occasion leads to drunkenness and as a result, speech
becomes slurred (insulting and demeaning), vision is blurred (unclear) and reaction times
are slowed.
CARBOXYLIC ACIDS
The carboxylic acids form another homologous series with carboxyl functionalgroup –COOH.
So all carboxylic acids have –COOH attached to their hydrocarbon chain. They have a general
formula CnH2n+1C00H, where n starts with zero for the first member in the family.
All member of this family have their name end with –oic. The following are the first-four members
of this homologous series:
The physical properties of the first-four members of the carboxylic acid are shown in the table
below.
Note: Ethanoic acid will solidify if the temperature falls only slightly.
Methanoic acid is present in nettle stings and ant stings, while ethanoic acid, the most well known, is
the main constituent of vinegar (well known for the acid in vinegar).
During this reaction, the orange potassium dichromate (VI) solution changes green.
Carboxylic acid, even though it is a weak acid, undergoes all acid reactions. That is
(a) Carboxylic acids, when dissolves in water can dissolve to form hydrogen ion, H+. Only the
hydrogen in the functional group –COOH dissociate to produce hydrogen ion.
COOH C00- + H+
CH3COOH CH3COO- + H+
Note: carboxylic acids, being weak acids, partially dissociate into ions in water.
(b) Reaction with metals.
Carboxylic acids react with metals to form salt and hydrogen gas.
Carboxylic acids react with bases forming salt and water only.
Carboxylic acids react with carbonates to form salt, water and carbon dioxide.
E.g. Ethanoic acid + Calcium carbonate Calcium ethanoate + Water + carbon dioxide
(2) Esterification
Carboxylic acid (ethanoic acid) reacts with alcohol (ethanol) in the presence of concentrated
sulphuric acid to form sweet smelling ester (ethyl ethanoate).
Uses of Esters
(2) Natural fat and oil are naturally occurring esters which are used as energy storage compounds
by plants and animals.
(i) Citric acid– found in all citrus fruits e.g. lemons and oranges.
(ii) Ascorbic acid (vitamin C)– found in citrus fruit, brightly coloured vegetable such as pepper.
Macromolecules, otherwise known as Polymers, are giant (very large) molecules formed when
thousands of smaller molecules called monomers are joined together.
Macromolecules therefore made up of small repeating units known as monomers. These units are
repeated any number of times, from about a hundred to more than a million.
Synthetic polymers, often called plastics, are man-made polymers that are formed by:
This is a process whereby identical monomers molecules add or join together to form only one
product called polymer.
For example,
Small molecules of ethenes (monomers) add together to form long chains of atom called
polyethene (polymer).
This is a process of reacting two or more differentchemical monomers together to form a polymer.
They are therefore said to be copolymers.
Each time the monomers are joined together to form a polymer, water is eliminated, because of this,
it is called condensation polymerisation.
Nylon
Nylon is a polymer of two different monomers, a carboxylic acid -COOH and an amine –
NH2monomers. These molecules react together to form amide linkage-CONH.
Each monomer consists of a chain of carbon atoms (which are shown in the structures as boxes). At
both ends of the monomers are functional groups. An amine group (-NH 2) on the first monomer
reacts with a carboxylic groug (-COOH) on the second monomer to make a an amide link (CONH)
between the two molecules. And each time a link is made, a water molecule is lost. As a result, this
type of polymer is known as a condensation polymer.
328
Because amide linkages are formed during the polymerisation, nylon is therefore known as
Polyamide.
Terylene
A terylene polymer chain is made up of carboxylic acids and alcohols. As these molecules react, they
form a link called ester–COO.
Terylene is therefore a condensation polymer made from two monomers. One monomer has an
alcohol group (-OH) on both ends, it is therefore known as diol. The other monomer has a
carboxylic acid group (-COOH) at both ends, it is therefore known as dicarboxylic acid. When the
monomers react, an ester link (COO) is formed, with water being lost each time.
3 29
Because of the linkages (ester) formed during the polymerisation, terylene is known as Polyester.
Advantages of Plastics
As a result, plastics have taken over as replacement materials for metals, glass, wood as well as
natural fibres (cotton and wool).
Disadvantages of Plastics
Plastics pollute the environment as they are non-biodegradable i.e. there are no micro-
organisms that can break them down. So, plastics cannot be decomposed by bacteria in the
environment.
Plastics burn easily to release toxic fumes or poisonous gases because plastics are carbon
compounds.
Some modern plastics are suitable for re-use. However, such a re-use policy is not suitable
for most plastics.
They therefore either recycle or dispose.
Recycling is more economical and satisfactory than disposing plastic waste in landfill sites.
But there are problems with recycling because most plastics waste is a mixture of different
types.
All living organisms rely on polymers for their existence. These polymers range from the very
complex DNA that makes life possible to more straightforward proteins, carbohydrates and animal
fats and vegetable oil that keep living things running. Protein, fat and oil and carbohydrate are
therefore natural polymers obtained from food.
Proteins
Proteins are what cells are made of. All the tissues and organs of our bodies are made up of protein.
Also, enzymes, which are responsible for controlling the body’s chemical reactions, are proteins.
DNA makes life possible and allows living things to reproduce, but without proteins there would be
no structure or chemistry to keep the living things going.
Proteins are built from amino acids monomer. That is amino acids are the monomers molecules use
for making protein polymers.
There are twenty (20) different amino acids. Each amino acid contains two functional groups, a
carboxylic acid –COOH and an amine –NH2 functional groups.
Two of the simplest amino acids are glycine and alanine. When they react together by condensation
polymerisation, an amide or peptide linkage is formed to produce a dipeptide (two amino acids
joined together).
Diagram 331
When this is repeated many times using different amino acids, a polymer is formed. Short polymers,
up to 15 amino acids are known as peptides. Chains with between 15 and 100 amino acids are
known as polypeptides. Chains involving more than 100 amino acids are called proteins.
Proteins therefore are polymer similar to nylon as they possess the same amide linkage-CONH but
with different units and the amide linkage is called Peptide Linkage (not polyamide) in the case of
protein. Protein therefore is polypeptide.
Hydrolysis of Proteins
Hydrolysis is the reaction of a compound with water. Therefore proteins can be broken down to
obtain the original amino acids by the process of hydrolysis. This is done by heating it in
concentrated hydrochloric acid. This is the reverse of the condensation process that made them.
331
Note: The mixture of amino acids can be separated by chromatography. Amino acids are colourless
substances, so a locating agent is used. It reacts with the amino acids to produce coloured spot.
Fats are formed by condensation reaction of fatty acid and glycerol. Glycerol contains three –OH
functional group per molecule and hence known as triol. Each molecule of glycerol then combines
with three molecules of fatty acid and form one molecule of fat (polymer).
Fats therefore have the same ester linkage –COO as Terylene. So, the ester linkage that joins the
monomers units in the man-made fibre Terylene also occurs in animal fats and vegetable oils, but
with different linking units. They are therefore known as polyester.
They are an energy source, lipids provide about twice as much as energy per gram as do
carbohydrates.
They provide thermal insulation for the body.
Some vitamins, for example A, D and E are insoluble in water but soluble in lipids. Therefore
foods containing lipids provide these vitamins.
Lipids are an essential part of cell membranes.
Hydrolysis of Fats
Soap is a product of the hydrolysis of fats. Fat is boiled with aqueous sodium hydroxide (NaOH), an
alkali, and is broken down in the presence of water (hydrolysed) to produce soap. This reaction is
known as saponification.
Diagram
Note: Just as the ester links in natural fats anod oils can be broken down by alkaline hydrolysis,
Terylene can be broken down by hydrolysis also.
Carbohydrate
A carbohydrate is a compound containing carbon, hydrogen and oxygen only. The ratio of hydrogen
and oxygen is always 2:1 (as in water). It is an important source of energy in our bodies and in all
living organisms.
Carbohydrate (starch) is a condensation polymer in which sugar molecules, such as glucose, are
joined together (C6H12C6). So, all long chain carbohydrates (polysaccharides) are long-chain
condensation polymer of glucose molecules (monosaccharide). In other words, the condensation
polymerisation of sugar (glucose) monomers produces long-chain carbohydrates.
Starch and glycogen are two different polysaccharides of glucose, a monosaccharide. They store
glucose in an insoluble from in plants and animals respectively. When energy is needed, cells break
down the starch or glycogen back to glucose. The glucose is then oxidized by respiration. Cellulose
is a third polymer of glucose. It forms the fibrous structure of plant cell walls.
These three polymers differ in the way in which the glucose monomers units are linked together.
Hydrolysis of carbohydrate/Starch
Polysaccharides (Starch) can be broken down or hydrolysed by acid hydrolysis. That is, if starch is
boiled with dilute hydrochloric acid (HCl), it is broken down into its monomers, glucose molecules.
The sugars present in the hydrolysis mixture can be analysed by chromatography. A locating agent
must be used to detect the spots because sugars are colourless,
Note: The presence of starch can be detected by testing with iodine solution: the solution turns a
deep blue colour or blue-black.