ORGANIC CHEMISTRY

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:

Organic chemistry is the study of carbon-containing compounds.

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.

The Unique Properties of Carbon

There are three special features of covalent bonding involving carbon:

 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.

Member of homologous series have the following properties:

(1) Same general formula.

Alkanes, for instance, form a homologous series with the same general formula C nH2n+2.

(2) Similar chemical properties.

(3) Different physical properties.

Members of homologous series differ in physical properties i.e. melting and boiling points. This is
due to the different number of carbon atoms in each compound. The more the carbon atoms, the
greater the inter-molecular forces; hence the more difficult it takes to break the molecules apart as
more heat will be needed. In other words, the more the number of carbon atoms, the higher the
melting and boiling points.

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.

Structural formulae of the first six alkanes are shown below.

Naming members of the alkane family

 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.

1. Methane – CH4 2.Ethane – C2H6

3. Propane – C3H8 4. Butane – C4H10

5. Pentane – C5H12 6. Hexane – C6H14

Physical properties of alkanes

Alkanes Relative Chemical Name Boiling Point Physical State at

Molecular Mass r.t.p.
Methane 16 CH4 -164 Gas
Ethane 30 C2H6 -87 Gas
Propane 44 C3H8 -42 Gas
Butane 58 C4H10 0 Gas
Pentane 72 C5H12 36 Liquid
Hexane 86 C6H14 69 Liquid
Heptanes 100 C7H16 98 Liquid
Octane 114 C8H18 126 Liquid

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.

Chemical reaction of alkanes

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

(1) Combustion reaction

Alkanes burns in air (oxygen) to give carbon dioxide and water, e.g.

CH 4 (g)+2 O2 (g)→ CO2 (g)+2 H 2 O g

C 2 H 6 ( g)+7 O2 (g)→ 4 CO 2 (g)+6 H 2 O(g)

C 3 H 8(g)+5 O2( g)3 CO 2(g)+4 H 2 O(g)

(2) Substitution reaction (Halogenation)

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.

CH 4 (g)+Cl 2(g) →CH 3 Cl(g) + HCl( g)

In the above reaction, one hydrogen atom of methane is substituted for by a chlorine atom.

Other substituted products are

CH 2 Cl 2 CHCl 3 CCl 4

Di-chloromethane tri-chloromethane tetra-chloromethane

Uses of Alkanes

Alkanes are some of the most useful fuels, e.g.

(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.

(4) Octane is used as fuel in car engines.

Isomers

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.

Naming members of alkenes family

 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.

The first-three alkenes and their structure are as shown below:

The physical properties of the first-five alkenes

No of Alkene Formula Relative Melting Boiling Physical

carbon molecular mass point 0C point 0C state at r.t.p.
atoms
2 Ethene C2H4 28 -164 -104 Gas
3 Propene C3H6 42 -185 -47 Gas
4 Butene C4H8 56 -184 -6 Gas
5 Pentene C5H10 70 30 Liquid

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

Pentene – C5H10 Methyl butene – C 5H10

Manufacture of alkenes

Few alkenes occur in nature. Most alkenes used by the petrochemical industries are obtained from
a process known as catalytic cracking.

(1) 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:

E.g. (i) C 12 H 26(l) →C 10 H 22(l )+ C2 H 4(g)

(ii) C 13 H 28 → C 8 H 18(l )+C 2 H 4(g) +C 3 H 6(g)

Octane Ethene Propene .

Note : There are essentially three uses of cracking. They are:

 To breakdown large alkanes into small ones;

 To produce alkenes;
 To produce hydrogen gas.

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.

Ethanol Ethene + Water

C2H5OH (l) C2H4 (g) + H2O (l)

The chemical reaction of alkenes

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

(i) Addition of Hydrogen (Hydrogenation)

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.

Ethene + Hydrogen Ethane

C2H4 (g) + H2 (g) C2H6(g)

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.

(ii) Addition of Water (Hydration)

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.

E.g. Ethene + Water Ethanol

C2H4 (g) + H2O (l) C2H5OH (l)

Propene + Water Propanol

C3H6 (g) + H2O (l) C3H7OH (l)

(iii) Addition of bromine (Bromination)

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

C2H4 + Br2 C2H4Br2

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.

(iv) Addition Polymerisation

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.

For example, ethene molecules are polymerized to form polyethene.

Diagram 326
This reaction can be summarized by the equation:

Where n is a very large number of ethene molecules.

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

Other additional polymer are

 Poly(chloroethene) or Polyvinyl chloride (PVC) or Teflon produced from chloroethenes or

vinyl chlorides

327
  Polytetrafluoroethene (PTFE) produced from tetrafluoroethene.

Uses of Addition Polymers

Polymer (and trade name(s) Monomer Properties Uses

Poly(ethene) Ethene Tough, Plastic bags, bowls,
(polyethylene, polythene, Durable bottles, packaging
PE)

Poly(propene) Propene Tough Crates and boxes,

(polypropylene, Durable plastic rope
PP)
Poly(chloroethene) Chloroethene Strong, hard (not Insulations, pipes and
(Polyvinyl chloride,PVC) flexible as polythene guttering
Poly(tetrafluoroethene) Tetrafluorethene Non-stick surface, Nonf-stick frying pans,
Polytetrafluoroethylene, withstands high non-stick taps and
Teflon, PTFE) tdmperatures joints.

2. Combustion reaction

Alkenes like alkanes, burns in oxygen to form carbon dioxide and water with a lot of heat, e.g.

C2H4 (g) + 3O2 (g) 2CO2 (g) + 2H2O (l) + Heat

C4H8 (g) + 6CO2 (g) 4CO2 (g) + 4H2O (l) + Heat

Uses of alkenes

 They are used mainly in plastic industry to produce plastics.

 In the production of alcohol such as ethanol.
 ALCOHOL

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

Naming members of alcohol family

All members of alcohol have name ending with –ol. Below are the structure, name and formula of
the first-four members.

Methanol – CH3OH

Ethanol – C2H5OH Propanol – C 3H7OH

Butanol – C4H9OH Butanol – C 4H9OH

Physical Properties of Alcohol

Atoms Chemical Chemical Relative Boiling point Physical State

Names Formula Molecular 0
C at r.t.p.
Mass
1 Methanol CH3OH 32 64 Liquid
2 Ethanol C2H5OH 46 78 Liquid
3 Propanol C3H7OH 60 97 Liquid
4 Butanol C4H9OH 74 117 Liquid
5 Pentanol C5HIIOH 88 137 Liquid

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

Ethanol can be produced by fermentation as well as by the hydration of ethene.

(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 .

The processes are as follow:

 The starch granules are first extracted by crushing, then cooked.

 Yeast is then added and left at room temperature for several days (about a week) in an
anaerobic condition (absent or oxygen free environment) to ensure that oxidation to acid
does not take place.
 After this, the fermented mixture is filtered and the alcohol (ethanol) is obtained by
fractional distillation.

Glucose Ethanol + Carbon dioxide

C6H12O6(aq) 2C2H5OH (l) + 2CO2 (g)

Alcoholic drinks such as beer or wine are made on a large scale.

 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.

(2) Catalytic Addition of Steam to Ethene (Hydration)

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.

Ethene + Steam Ethanol

C2H4 (g) + H2O (g) C2H5OH (l)

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

There are three important reactions of alcohols.

(1) Combustion reaction

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.

Ethanol + Oxygen Carbon dioxide + Water

C2H5OH (l) + 3O2 (g) 2CO2 (g) + 3H2O (g)

This reaction is highly exothermic i.e. it produces a great deal of heat.

(2) Oxidation reaction

Ethanol is slowly oxidised to ethanoic acid by bacteria in the air.

Ethanol + Oxygen Ethanoic acid + Water

C2H5OH (l) + O2 (g) CH3COOH (aq) + H2O (l)

This reaction is the reason why wine goes sour when left in the air. But ethanol can be
oxidisedmuch more quickly in laboratory by heating it with an oxidizing agent such as the acidified
potassium dichromate (VI) which changes from orange to green.

Diagram

Vinegar therefore is a weak solution of ethanioc acid, previously called acetic acid. It is produced
commercially by biochemical oxidation using bacteria (Acetobacter).

Wine can also become vinegar if it is left open to the air.

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.

Ethanol + Ethanoic acid Ethyl ethanoate + Water

C2H5OH + CH3COOH (l) CH3COOC2H5 (l) + H2O (l)

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.

(3) It is used in making beer, wine and all alcoholic drinks.

(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.,

(6) Also some food flavourings are made from ethanol.

Alcohol and Health

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.

For these reasons, some cultures forbid it.

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.

Naming members of carboxylic acid

All member of this family have their name end with –oic. The following are the first-four members
of this homologous series:

Methanoic acid - HCOOH Ethanoic acid – CH 3COOH

Propanoic acid – C2H5COOH Butanoic acid – C 3H7COOH

The Physical Properties of carboxylic acids

The physical properties of the first-four members of the carboxylic acid are shown in the table
below.

No of Chemical Name Chemical Melting point Boiling Point Physical State

Carbon Formula 0
C 0
C at r.t.p.
Atom
1 Methanoic acid HCOOH 9 101 Liquid
2 Ethanoic acid CH3COOH 17 118 Liquid
3 Propanoic acid C2H5COOH -21 141 Liquid
4 Butanoic acid C3H7COOH Liquid

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).

Formation of Ethanoic acid

Ethanoic acid is formed by

(1) Oxidation of ethanol through the atmospheric bacteria.

Ethanol + Oxygen Ethanoic acid + Water

C2H5OH (l) + O2 (g) CH3COOH (aq) + H2O (l)

(2) Using acidified potassium dichromate (VI)

C2H5OH (l) + 2[O] CH3COOH (aq) + H2O (l)

During this reaction, the orange potassium dichromate (VI) solution changes green.

Reactions of Carboxylic acid

Carboxylic acid undergoes two reactions. These are

(1) Acid reactions

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.

E.g. Ethanoic acid + Magnesium Magnesium ethanoate + Hydrogen

CH3COOH (aq) + Mg (s) Mg(CH3COO)2 (aq) + H2(g)

(c) Reaction with bases

Carboxylic acids react with bases forming salt and water only.

E.g. Ethanoic acid + Sodium hydroxide Sodium ethanoate + Water

2CH3COOH (aq) + NaOH (aq) NaCH3COO (aq) + H2O (l)

Ethanoic acid + Copper (II) oxide Copper (II) ethanoate + Water

2CH3COOH (aq) + CuO(s) Cu (CH3COO)2 (aq) + H2O (l)

(d) Reactions with carbonates.

Carboxylic acids react with carbonates to form salt, water and carbon dioxide.

E.g. Ethanoic acid + Calcium carbonate Calcium ethanoate + Water + carbon dioxide

2CH3COOH (aq) + CaCO3 Ca(CH3COO)2 (aq) + H2O (l) + CO2(g)

(2) Esterification

Carboxylic acid (ethanoic acid) reacts with alcohol (ethanol) in the presence of concentrated
sulphuric acid to form sweet smelling ester (ethyl ethanoate).

E.g. Ethanoic acid + Ethanol Ethyl ethanoate + Water

CH3COOH (l) + C2H5OH (l) CH3COOC2H5(l) + H2O (l)

The structure of ethyl ethanoate is shown be`low:

This reaction is called esterification.

Ethyl ethanoate is just one example of an ester. Members of the ester family have strong and
pleasant smell, many of which occurs naturally and are responsible for the flavours in fruits and the
smell/scent of flowers. They are therefore used for the following:

Uses of Esters

(1) They are therefore used in food flavourings and in perfumes..

(2) Natural fat and oil are naturally occurring esters which are used as energy storage compounds
by plants and animals.

(3) Ester group or linkage is found in man-made fibres such as Terylene.

Other carboxylic acids

(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.

(iii) Aspirin that is used as pain killer.

 MACROMOLECULES

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.

There are two kinds of macromolecules/polymers, these are:

(1) Synthetic polymer

(2) Natural polymer

(1) SYNTHETIC POLYMERS

Synthetic polymers, often called plastics, are man-made polymers that are formed by:

(i) Addition polymerisation

(ii) Condensation polymerisation

(i) Addition Polymerisation

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).

Polymers formed by addition polymerisation are called addition polymers.

Other addition polymers are:

 Polypropene produced by Propene.

 Polychloroethene/Polyvinylchloride (PVC) produced by Chloroethene/VinylChloride.
 Polytetraflouroethene (PTFE) produced by Tetraflouroethene

Note: Addition polymers are homopolymers (containing just one monomer).

 (ii) Condensation Polymerisation

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.

The polymers formed as a result of condensation polymerisation are regarded as condensation

polymers. Examples are Nylon and Terylene.

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.

Uses of Nylon and Terylene

 Nylon and Terylene are used to make synthetic (man-made) fibres.

 Nylon fibres are used to make ropes, fishing lines, shirts, ties and clothes for raincoats and
parachutes.
 Nylon is not just made into fibres. It can be moulded into strong plastic items such as gear-
wheel.
 Terylene fibres are for making clothing also. But terylene clothing is generally softer than
that made from nylon.

Advantages of Plastics

 Plastics are lighter than wood, stone or metal;

 Plastics are cheaper and relatively unreactive;
 Plastics can be easily moulded into any shape;
 Plastics do not corrode either in air or water;
 Plastics can be dyed bright colours.
 Plastics do not conduct heat or electricity; they can therefore be used as insulators.

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.

For this reason,

 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.

(2) NATURAL (BIOLOGICAL) POLYMER

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.

Fat and Oil

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.

Fats and oils (lipids) are an essential part of our diet.

 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.

The saponification of glyceryl stearate, a fat, is given below:

Glyceryl stearate + Sodium hydroxide Sodium stearate (soap) + glycerol

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.

The reaction is as follow

The carbohydrate (C6H10O5)n is a macromolecule and can be represented as

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,

Starch + Water nC6H12O6 (aq)

Note: The presence of starch can be detected by testing with iodine solution: the solution turns a
deep blue colour or blue-black.