ORGANIC CHEMISTRY

8.26.0 ORGANIC CHEMISRTY

8.14.0 CLASSIFICATION & NOMENCLATURE OF ORGANIC COMPOUNDS

BASICS:

 Organic compounds are a family of compounds that have chains or rings of

carbon atoms bonded to atoms of hydrogen and sometimes oxygen, nitrogen,
and other elements.
 Examples of organic compounds are hydrocarbons (alkanes and alkenes),
alcohols, carboxylic acids, polymers, esters, starch, cellulose and proteins.
 Hydrocarbons are compounds which contain carbon and hydrogen only.
 Alkanes and alkenes are examples of hydrocarbons.
 A homologous series is a group/family of compounds with a general formula,
similar chemical properties and showing a gradation (gradual change) in
physical properties as a result of increase in the size and mass of the
molecules, e.g. melting and boiling points; viscosity; flammability.
 CHARACTERISTICS OF A HOMOLOGOUS SERIES:
 All members of homologous series have same general formula.
 All members have the same functional group - the part of the substance where
reactions happen.
 Formula of each member differs to the next by –CH2.
 Physical properties change gradually as carbon atoms increase.
 The members have similar chemical properties
 Alkanes, alkenes, alcohols and carboxylic acids are examples of individual
homologous series.
 The group that identifies an organic molecule and gives it its chemical properties is
called its functional group.
 Alkane – general formula CnH2n+2
 Alkene - general formula: CnH2n and the C=C bond is the functional group.
 Alcohol - have the general formula: CnH2n+1OH. The -OH group (hydroxyl
group) is the functional group of alcohols.

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 Carboxylic acid - have the general formula: CnH2n+1COOH and –COOH group
(carboxyl group) is the functional group.
 Polymers are macromolecules made of repeating units called monomers.
 Addition polymerisation is which small molecules (monomers) join together to form
one molecule as the only product. All atoms in the monomer are used to form the
polymer, double bonds in molecules break in order to form new bonds.
 Condensation polymerisation – 2 different monomers join, double bonds are not
broken. In order for the monomers to join, a small molecule has to be expelled like
H2O (water) or HCl.
 Esters are produced when carboxylic acids react with alcohols; the functional group is
the ester link (-COO-, a carbon with a double bond to oxygen and a single bond to
another oxygen).
 Organic compounds may have straight chains or branched chains.

NOMENCLATURE OF ORGANIC COMPOUNDS

1. Naming straight chain organic compounds

 Nomenclature is the assigning of names to members in families of organic compounds.
 Organic compounds are named according to the number of carbon atoms in the
molecule (see the table below).

Number Name Prefix Alkane Alkene Alcohol Carboxylic acid

of
Carbon
Atoms
1 meth methane ------- methanol methanoic acid
2 eth ethane ethene ethanol Ethanoic acid
3 prop propane propene propanol Propanoic acid
4 but butane butene butanol Butanoic acid
5 pent pentane pentene pentanol Pentanoic acid
6 hex hexane hexene hexanol Hexanoic acid
7 hept heptane heptene heptanol Heptanoic acid
8 oct octane octene octanol Octanoic acid
The prefix denotes the number of the carbon atoms and the suffix denotes the
family name.
 The name begins with a prefix that tells you how many Carbons are in the
chain.
 C1 = Meth-, C2 = Eth-, C3 = Prop-, C4 = But-, C5 = Pent-
 After 5 the prefixes are the same as for Polygons in Maths (Hex-, Hept-, Oct-,
Non-, Dec- and so on).
 We can remember the first 5 as: My Evil Plane Bombed Paris.
 The name ends with a suffix that tells you the family name of the organic
compound
Suffix (Name ending) → Family name
“ane” → alkane
“ene” → alkene

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“ol” → alcohol
“oic acid” → carboxylic acid
“yl”, “oate” → ester (as in ethyl ethanoate)
TABLE: The nomenclature of some straight chain organic compounds
NAME OF FAMILY,FORMULA & STRUCTURE
NUMBER Alkane Alkene Alcohol Carboxylic acid
OF Functional group Functional group: Functional group Functional group
CARBON ----- C=C -OH -COOH
ATOMS
1 Methane CH4 NB. Methene, CH2, Methanol CH3OH Methanoic acid HCOOH
does not exist.

2 Ethane C2H6 Ethene C2H4 Ethanol C2H5OH Ethanoic acid CH3COOH

3 Propane C3H8 Propene C3H6 Propanol C3H7OH Propanoic acid

C2H5COOH

4 Butane C4H10 Butene C4H8 Butanol C4H9OH Butanoic acid C3H7COOH

5 Pentane Pentene Pentanol Pentanoic acid

6 Hexane Hexene Hexanol Hexanoic acid

EXERCISE: Please complete the last two rows of this table by writing the formulae
and drawing in the structures of the missing organic compounds. Substitute the
number of carbon atoms (n) into the general formulae so as to get the formulae of
the compounds.

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2. The nomenclature of branched chain organic compounds
Naming any organic molecule is straightforward if you follow these rules:
1. Find the longest carbon chain and name it. For example, a chain of five carbon
atoms will have a name based on pentane.
2. Number the carbon atoms in the chain so that the functional group has the lowest
possible number.
3. Identify any branches joined onto the main chain and name them.
4. Identify each branch by a number indicating its position. If more than one branch is
present then a prefix must be used (Di = 2 branches, Tri = 3 branches, Tetra = 4
branches).
NB. Be careful when naming molecules to number the longest possible carbon chain, and
that when writing the name, you follow the convention of using commas between numbers
and dashes between numbers and words.
Examples:
Name the following organic compounds:

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EXERCISE
Name the following organic compounds.

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8.27.1 ISOMERISM

ISOMERS
 Isomers are compounds with the same molecular formula but different
structural formulae.
 Due to different chain length, isomers have different physical properties (e.g.
boiling point).
 Isomerism is the existence of two or more molecules that are isomers.

STRUCTURAL ISOMERS OF ALKANES

 What is a structural formula? The structural formula (also called the displayed
formula) shows how the atoms are joined together in the molecule.
 Isomers of hydrocarbons have the same number of carbon and hydrogen atoms
but the carbon atoms are joined to each other in different ways. Simply
changing the shape of the molecule does not make it a different isomer.
 The isomers of some alkanes are shown below.
 Different isomers are different molecular compounds.
 They will have different physical properties (for example different boiling
points).
 The more carbon atoms a compound has, the greater the number of isomers
there can be.

 Methane (1 carbon atoms) has 0 isomers.

 Ethane (2 carbon atoms) has 0 isomers.
 Propane (3 carbon atoms) has 0 isomers.
 Butane (4 carbon atoms) has 2 isomers.
 Pentane (5 carbon atoms) has 3 isomers.
 Hexane (6 carbon atoms) has 5 isomers.
 Heptane (7 carbon atoms) has 9 isomers.
 Octane (8 carbon atoms) has 15 isomers.

 There are also isomers of alkenes and alcohols.

What are the Isomers of Butane?

 Butane (C4H10) has two structural isomers:

1) n-butane
2) 2-methylpropane.

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 Isomer 1 is the straight chain normal structure for butane (called n-butane).

 Isomer 2 (called 2-methylpropane) is a different structure with a branched chain

which has a carbon* atom joined onto three other carbon atoms.

 The two isomers are different compounds with different boiling points.
 Note that for both isomers, each carbon atom has four bonds (valency 4), and
each hydrogen atom has one bond (valency 1).
Valency is the combining power of an atom. You cannot change the number of
bonds which each atom has.
 Changing the shape of the molecule does not produce a different isomer.

What are the Isomers of Pentane?

 Pentane (C5H12) has three structural isomers: pentane, 2-methylbutane and
2,2-dimethylpropane.
 The fig below shows the three isomers and their nomenclature (naming).

Assignment: Draw the structural formulae of the five isomers of hexane and
name each isomer appropriately.

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8.28.0 HYDROCARBONS

8.28.1 ALKANES & ALKENES

 Hydrocarbons are compounds which contain carbon and hydrogen only.
 Alkanes and alkenes are examples of hydrocarbons.
 Alkanes are saturated hydrocarbons. Saturated means they only have single
bonds (i.e. they do not have double or triple bonds).
 Alkenes are unsaturated hydrocarbons. Unsaturated means they have double
bonds between some of their carbon atoms.

ALKANES
 Usually found in fuels, examples: natural gas, petrol, diesel, paraffin and
kerosene.
 Are a homologous series
 Have a general formula of CnH2n+2
 Example: propane has three carbon atom, thus n=3. Then the formula of
propane is C3H8
- Ends with suffix –ane
- Next alkane formula differ by –CH2 atoms. E.g. methane: CH4, ethane: C2H6
Structure of Alkanes
Shows how all atoms in a molecule joined together by drawing lines between
atoms to represent the bonds
Example: butane has a formula of C4H10, therefore the structural formula is:

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 It has 4 carbon atoms bonded together with 10 hydrogen atoms
 Organic compound containing single bonds only is saturated. E.g. methane.
 All alkanes are saturated. All alkenes are unsaturated

Physical Properties of Alkanes

 Melting points and boiling points increase as the molecules become larger and
heavier which increases the intermolecular forces of attraction between
molecules so more energy (from heat) is needed.
 Alkanes are insoluble in water but soluble in organic solvents such as
tetrachloromethane (CCl4).
 Alkane density increases down the series; all alkenes are less than 1g/cm3
 Alkanes become more viscous (uneasily flow) going down the series as the
longer molecules tangles together when it flows.
 Alkanes become less flammable down the series as B.P. becomes larger
 Alkanes are unreactive with either metals, water, acids or bases because the C
– C and C – H covalent bonds are harder to break.

REACTIONS OF ALKANES
 Each carbon atoms in an alkene has four covalent single bonds – this makes
them quite unreactive.
 They only have two reactions:
 1. COMBUSTION this can either be complete combustion or incomplete
combustion.
Complete combustion: meaning there is enough oxygen supply so water and
carbon dioxide form.
e.g. CH4 + 2O2 → CO2 + 2H2O

EXPERIMENT: To demonstrate the complete combustion of a hydrocarbon, such as

alkane, produces water and carbon dioxide.
 When Hydrogen atoms in alkanes react with Oxygen it always forms Water
Vapour (H2O)

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 If there is enough Oxygen for complete combustion then each Carbon atom will
bond to two Oxygen atoms to form Carbon Dioxide (CO2).
 We can show this by drawing the gases from a burning Hydrocarbon (a candle)
through a cold U-tube and another filled with Limewater.
 The Limewater turns milky, showing the presence of Carbon dioxide.
 A colourless liquid condenses in the tube. This liquid will turn dry Cobalt
Chloride paper from blue to pink, or Anhydrous Copper sulphate powder from
white to blue. This shows that the liquid is water.
 Conclusion: carbon dioxide and water are the products of the complete
combustion of hydrocarbons such as alkanes.

Incomplete combustion: meaning there is not enough oxygen to burn them

cleanly so either carbon monoxide and water or carbon and water form.
e.g. 2CH4 + 3O2 → 2CO + 4H2O or CH4 + O2 → C + 2H2O

 2. CHLORINE SUBSTITUTION: sunlight is necessary.

A chlorine atom replaces a hydrogen atom in an alkane in the presence of
sunlight or uv. This can happen to all of the hydrogen atoms if there is enough
chlorine.
e.g. CH4 + Cl2 → (light) → HCl + CH3Cl / CH2Cl2 / CHCl3 / CCl4 these compounds
are called chloromethane / dichloromethane / trichloromethane /
tetrachloromethane.
In darkness chlorine substitution does not occur. This means sunlight or uv is
needed to initiate the reaction.

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ALKENES
 Are a homologous series
 have general formula CnH2n.
 all alkene names end with –ene.
 the formula of one alkene differs from the next by –CH2.
 have similar properties like alkane going down the series.
Structure of Alkenes
Is organic compound containing C = C double bond, said to be unsaturated
Reason: not all C atoms are bonded to the maximum no. of 4 other atoms.
For more detail on alkenes, see topic 8.14.0 on classification & nomenclature of
organic compounds.
The Importance of Ethene
Ethene is an alkene used to manufacture:
Ethanol – solvent & fuel
Poly(ethene) – PE plastic variations
Ethanoic acid – vinegar

REACTIONS OF ALKENES

1. COMBUSTION
Burns in air to form carbon dioxide and water (complete combustion).
Example: Ethene burns in air. Write the balanced equation for the reaction
C2H4(g) + 3O2(g) → 2CO2(g) + 2H2O (l)
Incomplete combustion forms soot and CO. Its produced more than alkane.

2. ADDITION REACTIONS OF ALKENES

Addition reaction is the reaction of 2 or more molecules to form a single product.
The following are examples of addition reactions of alkenes:

Addition of hydrogen (hydrogenation)

 Alkenes react with hydrogen to form alkanes. This is called hydrogenation. Must
use nickel as catalyst and heat.
C2H4 (g) + H2 (g) → C2H6 (g)
Ethene + Hydrogen → Ethane

The Manufacture of Margarine - Hydrogenation of polyunsaturated vegetable

oils (oil containing C=C bond in their molecules) produces margarine.

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 Hydrogen is reacted with vegetable oil in the presence of nickel catalyst and
heat. Hydrogen adds to C=C bond, increasing the molecular mass of the
compound
 With increase in mass, the compound has higher boiling point. Therefore,
margarine is solid at room temperature.
 Since only some C=C bonds react with hydrogen, margarine is partially
hydrogenated and each type of margarine has different hardness, depending on
the number of C=C bonds remaining.

Addition of bromine
 Bromine adds to C = C double bond of alkane molecules. Phosphoric acid
(H3PO4), high temperature of 300oC and 60-70 atm pressure are needed as
catalyst.
 E.g. ethene to 1,2 –dibromoethene

C2H4 (g) + Br2 (g) → C2H4Br2 (l)

Nomenclature
(n) + (bromo) + (alkene name), where n is the number of bromine atoms.
E.g. Above, Ethene reacts with 2 bromine atoms producing DI(2)BROMO(Bromine)
ETHENE(alkene name). Hence we call the product DIBROMOETHENE.

Hydration of alkenes - Addition of water to alkenes (reaction of alkenes with

steam to form alcohol)
 Alkene reacts with water, in the form of steam, to produce alcohol.
 Alkene and steam are passed over phosphoric acid (H3PO4) catalyst at a
temperature of 300oC and pressure of 60 atmospheres. H2O molecules add to C=C
bonds to form alcohol.
 Example: Hydration of ethene (addition of water to ethene) produces ethanol:
Ethene + steam → Ethanol

C2H4 (g) + H2O (g) → C2H5OH (l) or CH3CH2OH (l)

Addition Polymerization
 The joining of several identical alkene molecules to form a polymer (large
molecule)
 E.g. (Ethene)n → Poly(ethene)
 (See full notes on Addition polymerisation is which small molecules (monomers) join together
to form one molecule as the only product.).

Testing for Unsaturated Compounds

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Mix bromine solution with alkene (for liquid alkenes – shake). Reddish-brown colour
of bromine disappears. This shows that the compound is an alkene i.e. is
unsaturated [contains double bond(s)].

How to Tell an Alkane from an Alkene? - Alkenes decolourise bromine water

whereas alkanes do not.

 An alkene e.g. ethene may be distinguished from an alkane e.g. ethane by

shaking the hydrocarbons with bromine water.
 Bromine water is brown or orange, and will lose its colour when it reacts with
the double bond of an alkene.
 Bromine water will stay brown with an alkane because an alkane has no double
bonds.
 Bromine adds across the double bond of an alkene to form a colourless dibromo
alkane. This is an example of an addition reaction.

What is the Cracking of Hydrocarbons?

 After the fractional distillation of crude oil there are too many large
hydrocarbons and not enough small hydrocarbons to meet the public's demand.
 Some of the large hydrocarbons (the heavier fractions) are broken down into
more useful smaller hydrocarbons (lighter fractions) by a process known as
catalytic cracking.
 The fractional distillation of crude oil produces mainly large alkanes.
 The purpose of cracking larger alkanes is to produce smaller, more useful
alkanes (such as petrol), and even more useful alkenes (such as ethene)
 Cracking is the main source of alkenes.
 See also the dehydration of ethanol to produce ethene.

What is the Chemistry of the Cracking of Hydrocarbons?

 Catalytic cracking of hydrocarbons involves thermal decomposition of large

alkane molecules into smaller molecules in the presence of a catalyst.
 The hydrocarbons are boiled and the hydrocarbon gases are either mixed with
steam and heated to a very high temperature or passed over a hot powdered
catalyst of aluminium oxide (alumina), silica (silicon dioxide) or porous pot.
 The catalyst works by providing the hydrocarbon gases with a convenient surface
for the cracking to take place.

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 In the laboratory the catalytic cracking of a hydrocarbon such as cooking oil
can be done using the set up below. Do not crack highly flammable alkanes such
as octane in the lab for safety reasons. Crack cooking oil instead.

 For example, decane (an alkane with 10 carbons) can be cracked to produce
octane and ethene.

Decane octane + ethene

C10H22 (g) C8H18 (g) + C2H4 (g)
 Octane is used as petrol.
 Ethene is used in the manufacture of polymers.
 Cracking an alkane produces a smaller alkane plus an alkene.
 If you add up the number of hydrogen atoms in the above reaction, you will see
that there are 22 on each side.
 An alkene is produced because the original alkane does not have enough
hydrogen atoms to produce two more alkanes.
 NB. The total number of carbon and hydrogen atoms in cracked alkane should
equal the total number of carbon and hydrogen atoms in the products.

E.g. Octane can be cracked into simpler hydrocarbons such as the reaction
below. Suggest the possible identity of product x.

C8H18 (l) → C2H4 (g) + X + CH4 (g)

Number of C atoms in X = 8 – 2 – 1 = 5
Number of H atoms in X = 18 – 4 – 4 = 10

Therefore, product X is C5H10

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8.29.0 ALCOHOLS

CONTENTS

What is an Alcohol?
* Molecular Formula
* Structural Formula
* Functional Group
* Isomers
* Reaction with Carboxylic acids - Oxygen - Sodium
Ethanol
* Combustion - Dehydration – Formation
* Fermentation-ethanol, mahewu, indigenous beer brewing.
* Testing for ethanol using potassium dichromate
* Properties and Uses

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ALCOHOLS

 Alcohols are the organic compounds containing hydroxyl group (-OH) attached to
a carbon atom. These are obtained by replacing one or more hydrogen atoms of
hydrocarbons by hydroxyl group (– OH).

 The general formula of alcohol is CnH2n+1OH.

 Following are the molecular formulae and structural formulae of first five
members of homologous series of alcohol.

Number of Name Molecular Structural Formula

carbon Formula
atoms
1. Methanol CH3OH

2. Ethanol C2H5OH

3. Propanol C3H7OH

4. Butanol C4H9OH

5. Pentanol C5H11OH

Physical Properties of Alcohols

The important physical properties of alcohols are:

1. The lower members of alcohols are colourless liquids having a characteristic

smell and burning taste. While the higher members are colourless,
odourless, wax like solids.
2. Alcohols exist as associated molecules having inter molecular hydrogen
bonding as shown below:

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3. The lower members have low boiling points but higher members of alcohol
have high melting point.

4. The lower members are soluble in water but as the size of alcohol molecule
increases solubility in water decreases.
5. These are volatile and easily combustible.
6. These are bad conductors of electricity.
7. These are generally lighter than water.
8. Alcohols have intoxicating effect i.e. these are poisonous.

NOMENCLATURE OF ALCOHOLS

Alcohols are named by replacing „e‟ in the name of the parent alkane by ‘ol’.

The following rules are followed in naming alcohols:

1. The longest continuous chain containing the carbon bonded to OH group is

selected as the parent chain.
2. The carbon atoms in the chain are numbered in such a way that the carbon
atom carrying the hydroxyl group gets the lowest number. For example,

Name Structural Formula

Propan-1-ol

Propan-2-ol

Butan-1-ol

Butan-2-ol

Pentan-1-ol

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Pentan-2-ol

Pentan-3-ol

Ethanol (C2H5OH)
The formula for ethanol is C2H5OH

Manufacture of Ethanol

Ethanol can be prepared by the following two methods-

1. By hydration of ethene
2. By fermentation of carbohydrates

a. Manufacture of Ethanol by Hydration of Ethene

Ethene and steam are passed over phosphoric acid catalyst at a temperature of
300OC and a pressure of 60 atmospheres to form ethanol.

Hydration is an addition reaction. Water, in the form of steam, is added to C=C

bond in ethene to form ethanol.

b. Manufacture of Ethanol by Fermentation of sugar (carbohydrates)

 Sugar/starch is dissolved in water and the fungi called yeast is added to the
solution.
 The mixture is left to ferment in warm conditions (25-40°C) for several days in
anaerobic conditions (in the absence of air/oxygen).
 Fresh air is not allowed to enter the vessel in which fermentation is taking place
because air can oxidize ethanol into vinegar.
 The yeast produces two enzymes (biological catalysts), invertase and zymase.
 The enzyme invertase hydrolyses sucrose present in sugar solution to glucose
and fructose as given below :

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 The enzyme zymase then converts glucose and fructose to ethanol and carbon
dioxide gas.

 The excess yeast is filtered off to obtain a dilute solution of ethanol.

 If the ethanol content in the solution rises to around 15%, the yeast is killed, so
it is impossible to make pure alcohol by fermentation.
 If a more concentrated solution of ethanol is required it is purified through
fractional distillation.
 Fractionally distilling the ethanol takes advantage of the difference in boiling
point between ethanol and water. Water boils at 100°C while ethanol boils at
78°C.
 The liquid distilling at 78°C is 96% pure ethanol, it is impossible to get it to 100%
because the rest is water and this cannot be removed by simple distillation.

FRACTIONAL DISTILLATION OF DILUTE ETHANOL IN THE LABORATORY

 Beads or glass columns in the fractionating column increase surface area for
condensation and evaporation.
 Ethanol, having a lower boiling point (78C) than water (96C), vaporises first.
 The vapour is cooled in the condenser and condenses into liquid.
 The liquid is collected as the distillate.

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 The amount of water in the distillate increases as the boiling point of water is
approached.
 The fraction of ethanol distilled around 78oC is more flammable because it
contains less water.

THE HARMFUL EFFECTS OF ALCOHOL (ETHANOL)

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:

1. Impairment of coordination and judgement.

It is one of the many causes of road accident as it leads to blurred vision and
reduced reaction time.

2. 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.
3. Liver cirrhosis (damage and deterioration of liver).

Prolonged and excessive consumption of alcohol causes liver cirrhosis which can
cause liver failure and death.

4. Also heavy drinking eventually damages the muscle tissue of the heart and
long–term damage to the brain.
All these health effects accelerate death.

5. 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).

6. Alcohol can make someone aggressive. This accounts for many arrests,
conviction and jail sentences.
7. Excessive drinking causes depression and other mental disorders.
8. 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 these
cancers.
9. Alcohol lowers the resistance of body towards diseases.

SOCIAL EFFECTS OF USING ALCOHOL

1. Abuse of alcohol leads to addiction and Alcoholism. Alcoholics are admitted
for treatment in institutions such as the Alcoholic synonymous and mental
hospitals.
2. Social problems e.g. bankruptcy, lack of self control, domestic violence,
divorces, public fighting, prostitution, accidents, absenteeism from work,
loss of jobs, poor performance at school and workplace etc.
3. Abuse of alcohol in cough medicines: Children may become addicted from
an early age.

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USES OF ETHANOL

1. Solvents
Ethanol is very important solvent which is used in industries for preparation of
paints, lacquers, dyes, varnishes, cosmetics and perfumes etc.
2. Fuels
Ethanol is a constituent of blend petrol and methylated spirits.
3. Preparation of Perfumes.
4. Alcoholic beverages
Ethanol is used for drinking purpose in the form of beer, whisky, rum and gin.
To avoid the misuse of ethanol meant for industrial processes, it is made unfit
for drinking purpose by adding small amount of CuSO4, methanol and pyridine in
it.
5. As an antiseptic in the form of rectified spirit.
6. Antifreeze in car radiators.
The mixture of ethanol and water is called antifreeze. Its freezing point is lower
than the freezing point of water. So, a solution containing antifreeze cannot
solidify even at very low temperature. So, antifreeze mixture is used in
radiators of cars in very cold countries.
7. For preparing ethanoic acid, ethene and esters.

Testing for ethanol using potassium dichromate

1. Add a few drops of the ethanol to a test tube containing potassium
dichromate (VI) solution acidified with dilute sulphuric acid.
2. Warm/heat test tube in a hot water bath.

Result

The orange solution turns green after heating:

Conclusion

Change of acidified potassium dichromate from orange to green shows the

presence of ethanol (alcohol).

PROPERTIES OF ETHANOL

Physical Properties

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1. It is a colourless, volatile liquid with characteristic pleasant odour.
2. It has boiling point of 78OC.

Chemical Properties
Following are the important chemical properties of ethanol.

1. Combustibility
Ethanol can easily burn in air to produce carbon dioxide and water.

2. Reaction with Na Metal

Ethanol Reacts With Sodium Metal To Produce Sodium Ethoxide And Hydrogen Gas

3. Dehydration of Ethanol

When ethanol is heated to 1600-1700C in the presence of sulphuric acid

(H2SO4) then a molecule of water is liberated and ethene is formed.

4. Oxidation of Ethanol by Potassium Permanganate

Ethanol can be converted into ethanoic acid by oxidation by KMnO4 as follows:

Esterification

Ethanol reacts with carboxylic acids in the presence of conc. H2SO4 as catalyst to
form sweet smelling substance called esters having general formula (RCOOR). This
process is called esterification.

INDIGENOUS BEER BREWING

SORGHUM BEER RECIPE

Source: https://www.kiva.org/blog/sorghum-beer-recipe

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Author: Austin Harris.

Ingredients:

1 kg. (2.2 lbs.) Sorghum

7g (1/4-ounce) Baking Yeast

Instructions:

1. Soak sorghum in water, allowing it to begin germination.

This process is called malting. The following are the purposes of malting the
sorghum:
 Develops enzymes which break down the grain‟s starches into
fermentable sugars such as glucose and maltose.
 Develops protease enzymes which break down the proteins in the grain
into forms that can be fermented by yeast.
2. Dry the malt or chimera (partially germinated grains).
3. Crush the sorghum malt (chimera) and boil in water for about 15 minutes.
4. Drain and put into a large vessel. Add 4 litres of hot water and let sit for 1
hour.
5. Transfer liquid portion of mash to a large vessel and add 8 litres of hot water.
Let the mixture cool naturally until reaching room temperature.
6. Add the yeast and one cup of additional crushed sorghum malt (from germinated
grains). Stir vigorously.
 The yeast contains zymase enzyme which ferments glucose in the grain to
ethanol:

 Natural enzymes which develop during malting also ferment the sugars in
the grain to ethanol.
7. Ferment for 2 days at room temperature then strain beer into storage vessels.
Serve to thirsty customers.

Sorghum Beer

African sorghum beer is a brownish-pink beverage with a slightly tangy and sour
taste. It has an alcohol content that can vary between 1% and 8%. Its appearance
is cloudy hence it is referred to as opaque beer. Traditionally it is consumed at
room temperature. Sorghum beer is known by the following names in Zimbabwe:
doro, hwahwa etc and the commercial version is called chibuku, scud etc.

MAHEWU
 Mahewu (a.k.a. magada) is a non-alcoholic home-brewed drink made of thin,
slightly fermented finger millet malt porridge or maize-meal porridge, often
with wheat flour added.
 Mahewu is a fermented gruel commonly consumed as a staple among black
Zimbabweans.
 The gruel is a thin drinkable porridge made from fermented cereal malt such
as finger millet malt, maize-meal or sorghum/rapoko malt.

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 A similar, commercially manufactured mahewu drink is sold in cartons, or in the
form of an instant ready-mix.
 Finger millet is zviyo in Shona.
 Malt is chimera in Shona.
 So, finger millet malt in Shona is called chimera chezviyo.

How to make Mahewu (Finger Millet Malt Drink)

Source: http://www.zimbokitchen.com/how-to-make-mahewu-finger-millet-malt-
drink/
Author: Rumbie.

Ingredients Required

 200g finger millet malt

 2 1/2 litres hot water
 1 1/2 litres cold water
 Extra cold water to make paste

Equipment Required

 Large pot
 Flat rounded wooden spoon
 Measuring jug

Instructions

1. The ingredients you‟ll need for this are (200g finger millet malt
2 1/2 litres hot water; 1 1/2 litres cold water; and Extra cold water to make
paste) Put the finger millet malt in large pot.
2. Add a bit of cold water to make a smooth paste.
3. Put pot on stove top on medium-high heat. Add the boiling water whilst stirring
simultaneously and bring to the boil.
4. As soon as it is boiling, reduce heat to a gentle simmer and allow it to simmer
until cooked (about 40 minutes).
5. After about 40 minutes, it should now be cooked through and ready for the next
stage.
6. When it is cooked, remove from the heat and allow it to cool.
7. When it has cooled, add the cold water, again, whilst stirring simultaneously.
Do this until you get a “thinnish” liquid. (Thin enough to drink).
8. Your mahewu are now ready to be brewed!
9. Place your pot in a warm dry place until the beverage brews, stirring at least
once a day to ensure that nothing settles in the bottom
10. Your mahewu (finger millet drink) should be ready in about 4 days depending
on how warm the place was where you were putting it. You will know that it is
ready when it has a pungent flavour.

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8.30.0 CARBOXYLIC ACIDS

CONTENTS
 What is a Carboxylic Acid?
 Examples of Carboxylic Acids
 What is the Functional Group for a Carboxylic Acid?
 What is the Structural Formula of a Carboxylic Acid?
 What is Ethanoic Acid?
 How is Ethanoic Acid Formed?
 What are the Uses of Ethanoic Acid?
 The Reaction of Carboxylic Acids with Alcohols, Alkalis, Carbonates and
Metals
 Saponification

CARBOXYLIC ACIDS
Carboxylic Acids

What is a Carboxylic Acid?

 Carboxylic acids are organic molecules which form a homologous series with the
general formula CnH2n+1COOH.
 The –COOH group (carboxyl group) is the functional group of carboxylic acids.

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 Carboxylic acids are weak acids which react in the same way as dilute mineral
acids.
 Carboxylic acids are weak acids (partially ionises in water).
 They are named (like hydrocarbons) according to the number of carbon atoms in
the molecule.

Methanoic acid Butanoic acid

HCOOH, has n=1. C3H7COOH, has n=4.
Ethanoic acid Pentanoic acid
CH3COOH, has n=2. C4H9COOH, has n=5.
Propanoic acid Hexanoic acid
C2H5COOH, has n=3. C5H11COOH, has n=6.

Other examples of carboxylic acids are:

1. Aspirin - taken as a pain killer and to prevent blood clots

2. Citric Acid - found in oranges, lemons and some soft drinks

3. Tartaric Acid - used in baking powder for cooking

4. Vitamin C - called ascorbic acid, is found in fresh fruit and vegetables.

The four acids listed above are examples of acids that are solid when they are
pure.

The Structure of Carboxylic Acids

What is the Structure of Carboxylic Acids?

Methanoic acid (HCOOH) has the structural formula

Ethanoic acid (CH3COOH) has the structural formula

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Propanoic acid (C2H5COOH) has the structural formula

Butanoic acid (C3H7COOH) has the structural formula

The Reactions of Carboxylic Acids

What are the Reactions of Carboxylic Acids?

 Carboxylic acids react in the same way as dilute mineral acids.

1. Carboxylic acids react with bases/alkalis to form salt and water

(neutralization)

Carboxylic acids are neutralised by alkalis, for example

Methanoic acid + sodium hydroxide sodium methanoate + water

HCO2H(aq) + NaOH(aq) HCO2Na(aq) + H2O(l)

Ethanoic acid + potassium hydroxide potassium ethanoate + water

CH3CO2H(aq) + KOH(aq) CH3CO2K(aq) + H2O(l)

2. Carboxylic acids react with carbonates and bicarbonates to form salt, carbon
dioxide and hydrogen.

Carboxylic acids are neutralised by carbonates, for example

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Ethanoic acid + sodium carbonate →sodium ethanoate + carbon dioxide + water
2CH3CO2H(aq) + Na2CO3(s) → 2CH3CO2Na(aq) + CO2(g) + H2O(l)

Butanoic acid + zinc carbonate → zinc butanoate + carbon dioxide + water.

2C3H7CO2H(aq) + ZnCO3(s) → (C3H7CO2)2Zn(aq) + CO2(g) + H2O(l)

3. Carboxylic acids react with metals to form metal ethanoate (salt) and
hydrogen

Magnesium + ethanoic acid → magnesium ethanoate + hydrogen

Mg(s) + 2CH3CO2H(aq) → (CH3CO2)2Mg(aq) + H2(g)

zinc + propanoic acid zinc propanoate + hydrogen.

Zn(s) + 2C2H5CO2H(aq) (C2H5CO2)2Zn(aq) + H2(g)

4. Carboxylic acids react with alcohols in the presence of concentrated sulfuric

acid, to form sweet smelling substances called esters.

The reaction is called esterification. Concentrated sulfuric acid is a catalyst

for this reaction.
E.g. Methanoic acid will react with ethanol in the presence of concentrated
sulfuric acid, to form an ester called ethyl methanoate

Ethanol + methanoic acid ethyl methanoate + water.

C2H5OH(aq) + HCO2H(aq) HCO2C2H5(aq) + H2O(l)

Ethanoic Acid.

Preparation of ethanoic acid

1. Oxidation of alcohol in the presence of bacteria such as Acetobacter:

 When ethanol reacts with oxygen in air it forms a weak acid called ethanoic
acid. In an open bottle of beer or wine, the reaction happens naturally in the
presence of bacteria such as Acetobacter, and it is the ethanoic acid that can
make beer or wine taste sour.

Ethanol + oxygen ethanoic acid + water.

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

 Ethanoic acid can also be prepared by oxidation of ethanol in the presence of

oxidizing agent potassium dichromate (K2Cr2O7) or potassium manganate (VII)
(KMnO4) and (sulphuric acid) H2SO4.

 Ethanoic acid is a weak acid.

It is found in vinegar ("vinegar" is old French for "sour wine").
 Vinegar is used as a food flavouring and preservative.

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Physical Properties

Following are the physical properties of ethanoic acid:

 It is a colourless liquid with pungent odour.

 It freezes below 16.50C.
 Its boiling point is 1180C.
 It is soluble in water.

Uses of ethanoic acids

1. Manufacture of perfumes
2. Food preservation
3. Flavouring
4. Ethanoic acid is used to make a polymer called acetate rayon.
Acetate rayon fibres can be woven to make clothing and fabrics.

What is the Structure of Ethanoic Acid?

 The structure of ethanoic acid is shown in the picture below.

Ethanoic acid will react with alcohols, alkalis, carbonates and metals (see
Reactions of carboxylic acids).

Question: Write balanced equations to represent the reactions of ethanoic acid

with:

(a). Sodium hydroxide

(b). Sodium carbonate
(c). Sodium
(d). Butanoic acid.

PREPARATION OF CARBOXYLIC ACIDS

1. From natural gas

Natural gas is passed over air and catalyst to form ethanoic acid and water.
E.g. production of ethanoic acid from methane
2CH4(g) + 2O2(g) → CH3COOH(aq) + 2H2O(l)

2. Oxidation of alcohol

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Alcohol can be oxidized when left in air with bacterial enzymes as catalyst. The
products are carboxylic acid and water.
E.g. ethanol produces water and ethanoic acid when left in air.
C2H5OH(aq) + O2(g) →2CH3COOH(aq) + 3H2O(l)

ESTERIFICATION
 An Ester is a sweet smelling organic compound made from carboxylic acid and
alcohol with the removal of one molecule of water. Sulphuric acid is added as
catalyst then the mixture is heated.
 The reaction is called esterification.
 The carboxylic acid and alcohol are joined by an ester linkage (-COO-) with the
release of water.
 The general formula of esters is CnH2n+1COOCnH2n+1.
 The functional group of esters is the ester linkage (-COO-, a carbon with a double
bond to oxygen and a single bond to another oxygen):

EXAMPLES OF ESTERIFICATION REACTIONS

1. The reaction between Methanoic Acid with Alcohols to make Esters

Methanoic acid will react with alcohols in the presence of concentrated sulfuric
acid, to form esters.
Concentrated sulfuric acid is a catalyst for this reaction.

Methanol + Methanoic acid Methyl methanoate + water.

CH3OH(aq) + HCO2H(aq) HCO2CH3(aq) + H2O(l)

The structure of methyl methanoate:

Ethanol + Methanoic acid Ethyl methanoate + water.

C2H5OH(aq) + HCO2H(aq) HCO2C2H5(aq) + H2O(l)

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The structure of ethyl methanoate:

Propanol + Methanoic acid Propyl methanoate + water.

C3H7OH(aq) + HCO2H(aq) HCO2C3H7(aq) + H2O(l)

The structure of propyl methanoate:

Butanol + Methanoic acid Butyl methanoate + water.

C4H9OH(aq) + HCO2H(aq) HCO2C4H9(aq) + H2O(l)

The structure of butyl methanoate.

2. The Reaction of Propanoic Acid with Alcohols to make Esters

Propanoic acid will react with alcohols in the presence of concentrated sulfuric
acid, to form esters.
Concentrated sulfuric acid is a catalyst for this reaction.

Methanol + Propanoic acid Methyl propanoate + water.

CH3OH(aq) + C2H5CO2H(aq) C2H5CO2CH3(aq) + H2O(l)

The structure of methyl propanoate.

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Ethanol + Propanoic acid → Ethyl propanoate + water.

C2H5OH(aq) + C2H5CO2H(aq) C2H5CO2C2H5(aq) + H2O(l)

The structure of ethyl propanoate:

Propanol + Propanoic acid Propyl propanoate + water.

C3H7OH(aq) + C2H5CO2H(aq) C2H5CO2C3H7(aq) + H2O(l)

The structure of propyl propanoate:

Question: Identify and encircle the ester linkage (ester bond) in this structure.

Butanol + Propanoic acid Butyl propanoate + water.

C4H9OH(aq) + C2H5CO2H(aq) C2H5CO2C4H9(aq) + H2O(l)

The structure of butyl propanoate:

3. The Reaction of Butanoic Acid with Alcohols to make Esters

Butanoic acid will react with alcohols in the presence of concentrated sulfuric
acid, to form esters. Concentrated sulfuric acid is a catalyst for this reaction.

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Methanol + butanoic acid methyl butanoate + water.
CH3OH(aq) + C3H7CO2H(aq) C3H7CO2CH3(aq) + H2O(l)

The structure of methyl butanoate:

Ethanol + butanoic acid ethyl butanoate + water.

C2H5OH(aq) + C3H7CO2H(aq) C3H7CO2C2H5(aq) + H2O(l)

The structure of ethyl butanoate.

Propanol + butanoic acid propyl butanoate + water.

C3H7OH(aq) + C3H7CO2H(aq) C3H7CO2C3H7(aq) + H2O(l)

The structure of propyl butanoate:

Butanol + butanoic acid butyl butanoate + water.

C4H9OH(aq) + C3H7CO2H(aq) C3H7CO2C4H9(aq) + H2O(l)

The structure of butyl butanoate.

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NAMING ESTERS (ESTER NOMENCLATURE)

Ester name is [alcohol]yl [carboxylic acid]oate. For instance, example above is
butyl butanoate, where “butyl” is from butanol; “butanoate” is from butanoic acid

Hydrolysis of esters
 Esterification is reversible. We can add sodium hydroxide and heat mixture to
obtain carboxylic acid and alcohol from ester with the release of water. This is
HYDROLYSIS.

E.g. Propanoic acid reacts with butanol to form butyl propanoate in the
presence of sulphuric acid catalyst. This reaction is reversed by adding sodium
hydroxide. The butyl propanoate is hydrolysed back to butanoic acid and
propanol

Butanol +Propanoic acid Butyl propanoate + water.

C4H9OH(aq) + C2H5CO2H(aq) C2H5CO2C4H9(aq) + H2O(l)

USES OF ESTERS

An ester is a sweet smelling substance.

Following are the uses of esters:

1. Artificial fruit/food flavours in cold drinks, ice-creams and sweets etc.

2. Solvents for oils, fats and varnishes.
3. Making artificial perfumes.
4. Esters are used to make polymers called polyesters.

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Polyesters can be used to make plastic bottles or polyesters can be made into
fibres to make clothing. Recycled polyesters are used to make fleece clothing.

FATS/OILS (a.k.a. Lipids or tryglycerides)

 Fats and oils (triglycerides) are ester molecules with three ester linkages, hence
they are triesters.
 Fats and oils are esters formed by a glycerol molecule reacting with 3 fatty acid
molecules.

This can be simplified as shown below:

 Since glycerol is an alcohol, while fatty acids are carboxylic acid, the process is
called esterification, and it is a condensation reaction.
 Fats and oils (Triglycerides) are used to make soaps in a process called
saponification.

SAPONIFICATION
 The process of making soap by the hydrolysis of fats and oils with sodium
hydroxide is called saponification:

Fat or Oil + Sodium hydroxide → Soap + Glycerol

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 These fats and oils, called triglycerides, are ester molecules with three ester
linkages.

 Soap is made in factories by boiling fats and oils with sodium hydroxide. The
three ester linkages in fats/oils are broken down in the presence of water. This is
a hydrolysis reaction.
- +
 Glycerol and a sodium salt of a fatty acid (R—COO Na ) are formed.
 The sodium salt of fatty acid is used as soap. For example:

This can also be represented as shown below:

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Where R is a long chain of carbon atoms.

 This process of making soap by the hydrolysis of fats and oils with sodium
hydroxide is called saponification.
 The soap you buy may be made from vegetable oil – like palm oil or coconut oil –
or even from fish oil or animal fat.
 Artificial esters are added to make the soap smell nice.

Saponification of glyceryl stearate (a fat) gives a soap called sodium

stearate:

 There are many different types of triglycerides (fats and oils) used for
saponification:

Triglyceride Details
Tallow (fat) An animal fat derived from beef (or sheep) processing . Soaps
commonly made from tallow are hard, greasy soaps due to the
long chain length of tallow
Lard (fat) An animal fat derived from pigs. Produces hard soaps which
lather quickly but do not dissolve readily in water
Coconut oil A vegetable oil derived from the coconut fruit. Produces soaps
that are soft and which lather in salty or hard water
Palm oil A vegetable oil derived from the palm fruit. Produces soaps
that are similar to those made from tallow (hard and greasy)
due to the long chain length

The cleaning action of soap is explained as follows:

Soap molecule consists of a long hydrocarbon chain which is hydrophobic (water

hating) attached to an ionic „head‟ which is hydrophilic (water loving) (see Figure
below).

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When soap is put into water which has a greasy dish (or a greasy cloth) in it, the
hydrophobic hydrocarbon chain on each soap molecule becomes attracted to the
grease and becomes embedded in it (Figure).
On the other hand, the hydrophilic ionic head group is not attracted to the grease
but is strongly attracted to the water molecules. When the water is stirred, the
grease is slowly released and is completely surrounded by the soap molecules to
form structures called micelles. The grease is, therefore, „solubilised‟ and
removed from the dish. The soap is able to remove the grease because of the
combination of the covalent and ionic bonds present.

The Saponification Experiment (Soap making experiment)

1. Place 5g of NaOH pellets in a 100ml beaker.

2. Add 30ml of water
3. Add 5ml of vegetable oil e.g. coconut oil, cotton seed oil etc or animal fat
e.g. mutton fat or lad.
4. Using a Bunsen burner, bring the solution to a boil, taking care to stir
constantly so as to provide a uniform temperature.
5. Allow the solution to cool once the layer of oil has fully disintegrated.
6. Add 10g of NaCl and bring the solution once more to a boil, again taking
care to stir constantly.
7. Allow the solution to cool; lumps of soap should appear on top.
8. Decant the solution taking care to keep the product.
9. Flush the beaker with NaCl and decant successively.

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10. Place the soap on filter paper and allow the soap to dry in the fume
cupboard.

TRY THIS QUESTION

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8.31.0 POLYMERS

8.31.1 SYNTHETIC POLYMERS

WHAT ARE POLYMERS

 Polymers are macromolecules made of repeating units called monomers.

CLASSIFICATION OF POLYMERS

Polymers can be classified in two ways as given below:

1. Classification based on source of availability.

2. Classification based on method of synthesis.

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1. Classification based on source of availability
According to this classification polymers are of two types:

1. Natural polymers
2. Synthetic polymers

Natural Polymers
The polymers obtained from nature are called natural polymers. For example,
proteins, starch, cellulose, natural rubber, nucleic acids, etc. are common
examples of natural polymers.

Synthetic Polymers
The polymers which are manmade are called synthetic polymers. They are
prepared in laboratories by man. Examples of synthetic polymers are polythene,
nylon, Terylene, teflon, polyvinyl chloride (PVC) and synthetic rubber.

2. Classification of polymers on the basis of method of synthesis

On the basis of method of synthesis, the polymers are also of two types:

1. Addition polymers
2. Condensation polymers

Addition Polymers - A polymer formed by direct addition of repeated monomers

without the elimination of any molecule is called an addition polymer. Addition
polymers are prepared from unsaturated compounds especially alkenes. An
example of an addition polymer is poly(ethene) a.k.a. polythene.

Condensation Polymers - These polymers are formed by the condensation of two

or more different monomers with the elimination of small molecules, usually water
(H2O) or HCl. Polyesters and polyamides (e.g. nylon) are in this class of polymers.

SYNTHETIC POLYMERS are manufactured by Addition polymerisation is which small

molecules (monomers) join together to form one molecule as the only product.
e.g. polythene or by condensation polymerisation e.g. Terylene and Nylon.

1. ADDITION POLYMERISATION

 Addition polymerisation is reaction in which small molecules (monomers) join

together to form one molecule as the only product.
 Atoms in the monomer are used to form the polymer, double bonds in
molecules break in order to form a new bond.

MAKING POLYTHENE by addition polymerisation

Addition polymerisation is which small molecules (monomers) join together to form
one molecule as the only product.

 Many ethene molecules can be made to join together to form the polymer called
poly(ethene) or polythene.
 High temperature and high pressure are needed for the reaction to occur.

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 In this reaction the double bond is opened up, to form a link either side to
another molecule: note that double bonds are not present in the long chain
polymer. The polythene is actually an alkane and it is saturated.

 Use the diagram below to deduce the structure of a monomer (e.g. ethene)
from a polymer (e.g. polythene) and vice versa.

Uses of polythene: for plastic bags, plastic bottles (since it forms a flexible
film and is transparent), gloves, clingfilm, mugs, bowls, chairs and dustbins.

2. CONDENSATION POLYMERISATION

 Condensation polymerisation – 2 different monomers join, double bonds are

not broken. In order for the monomers to join, a small molecule has to be
expelled (lost) like H2O (water) or HCl (hydrogen chloride).
 Hence the name condensation since water is expelled.
 In condensation polymerisation two products are formed, the polymer and the
expelled small molecule.

MAKING NYLON by condensation polymerisation

Nylon is a synthetic condensation polymer produced from two different monomers.
One of the monomers has an amide group (NH2) and the other has a carboxylic
acid group (-COOH). Each time a link is made a molecule of water is lost. The link
formed is called an amide (or peptide link) so the resulting polymer is a polyamide
(polypeptide)

1. Making nylon (a polyamide/polypeptide) in industry:

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 The monomers are 1,6-diaminohexane (a.k.a hexane-1,6-diamine) and 1,6
hexane dicarboxylic acid (a.k.a adipic acid or hexanedioic acid).

 1,6-diaminohexane is an organic compound called an amine. It is a diamine

because it has two amino (-NH2) groups at both ends.
 1,6 hexane dicarboxylic acid is carboxylic acid. It is a dicarboxylic acid because
it has two carboxylic (-COOH) groups at both ends.
NB. According to your syllabus these monomers should be simplified by using block
diagrams like this:

 In industry, the monomers join to each other by eliminating a small molecule:

H2O (water).This is a condensation polymerisation. The industrial conditions are
350°C in the presence of hydrogen and a nickel catalyst.
 Thousands of monomers join together, giving a polymer called Nylon 6,6.
 The polymer is called Nylon 6,6 because it comes from two six-carbon
monomers. Some textbooks simply call it Nylon.

 Nylon is a polymer called a polyamide (polypeptide) since it has repeating

amide linkages (peptide linkages).

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 An amide linkage (a.k.a peptide linkage) has this structure:

2. Making nylon (a polyamide) in the laboratory:

 The monomers are 1,6-diaminohexane and hexan-1,6-dioyl chloride.

NB. According to your syllabus these monomers should be simplified by using block
diagrams like this:

 The condensation polymerisation to make Nylon 6,6 in the laboratory takes

place at room temperature and is represented as:

 HCl is expelled as a by-product.

 Nylon makes very strong fibres because of very strong intermolecular forces
between its chains in the form of hydrogen bonding.
 Uses of nylon: fabrics, carpet fibres, airbags, tyre cords, ropes, stockings,
seat belts, ballistic cloth, fishing lines and nylon can also be cast into solid
shapes for cogs and bearings in machines. Nylon melts instead of burning and so
has many military applications.
TRY THIS QUESTION
Describe the similarities and differences between the industrial and laboratory
manufacture of nylon.

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MAKING TERYLENE by condensation polymerisation

Making Terylene (a polyester):

The monomers are benzene-1,4-dicarboxylic acid and ethene-1,2-diol.

NB. According to your syllabus these monomers should be simplified by using block
diagrams like this:

 The monomers join by eliminating a water molecule. This is condensation

polymerisation since water is lost. Thousands of molecules join up, giving a
polymer called Terylene.

 Terylene is a polyester since it has repeating ester linkages.

Uses of Terylene:
1. Making clothes, dress materials and curtains.
2. Making conveyor belts.
3. Making sails of sail boats.

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8.31.2 NATURAL POLYMERS

Content
 STARCH
 PROTEIN

CARBOHYDRATES
 Carbohydrates (a.k.a saccharides) are organic compounds which contain
carbon, hydrogen and oxygen. Their general formula is Cn(H2O)n.
 Carbohydrates are natural condensation polymers made from simple sugars.
Starch, cellulose and glycogen are all polymers of glucose. The simple sugar
monomers are called monosaccharides and the polymers are called
polysaccharides. All monosaccharides have OH groups and it‟s these groups that
join together to make the polymer with the elimination of water.
 The simplest carbohydrate is glucose, formula C6H12O6.
 Glucose can be represented as shown below:

 The structure of glucose is simplified using block diagrams as shown below:

 Glucose monomers polymerise to form starch with the elimination of water in a

reaction called condensation polymerisation:

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 The overall condensation reaction is: nC6H12O6 →(C5H10O5)n + nH2O

 This can also be represented as shown below.

Glycosidic bond

The starch repeat unit is as follows:

 The repeat units are held together by linkages called glycosidic bonds ( - O - ).
 In plants the glucose made during photosynthesis is converted into starch for
storage.

Hydrolysis of carbohydrates in the laboratory

 Starch can also be broken down into glucose by heating with sulphuric acid.
This adds water molecule into the polymer.
 Water molecules break apart the glycosidic bond of the starch molecule, leaving
separate glucose molecules. This is hydrolysis which is the reverse of
condensation:

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 The overall hydrolysis reaction is: (C5H10O5)n + nH2O → nC6H12O6

Hydrolysis of starch during digestion

 During digestion enzymes, by hydrolysis, break down the starch we eat into
glucose molecules.
 These glucose molecules are transported around the body by blood. In the
bloodstream during assimilation, condensation reactions build the glucose
molecules up to produce glycogen for storage in the liver. Some of the glucose is
used in respiration to produce energy for metabolism.

TRY THESE QUESTIONS

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PROTEINS
 Proteins are natural condensation polymers made up from amino acid
monomers.
 Proteins are natural polymers made up of amino acids monomers by
condensation polymerisation.
 Different amino acid molecules are joined together in different orders within our
bodies to form different proteins.
 The body cannot make all the amino acids required to build different proteins. It
relies on protein intake from our diet to supply the essential amino acids.
 Amino acids have an amine group (-NH2) at one end and a carboxyl group
(-COOH) at the other end.

 Amino acids can be represented as shown above where the box or R represents
an alkyl group.
 When R is hydrogen the protein is called glycine. When R is –CH3 the protein is
called alanine.

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 When amino acids react they form an amide linkage (peptide linkage) like in
nylon. Water is lost. This is a condensation reaction.

 NB. An amide linkage is also called a peptide linkage.

 Proteins are polyamides (polypeptides) since they have repeating amide
linkages (peptide linkages).

TRY THESE QUESTIONS:

1. Using the diagram of the protein above identify and draw the following:
(a). The two monomers (amino acids) that make up the protein.
(b). The protein repeat unit.
2. The structural formulae of the two simplest amino acids, glycine and
alanine, are shown below.

(a). Encircle and label the following on any one of the amino acids:
(i) The amine group.
(ii) The carboxyl group.
(b). Using the structures of these two amino acids draw a diagram to show the
condensation polymerisation in which the two form a protein.
(c). Encircle and label the peptide linkage on your diagram in (b) above.

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Hydrolysis of proteins - Breaking down proteins
Hydrolysis of proteins in the laboratory
 Proteins can also be broken down by hydrolysis into amino acids by boiling
protein with sulphuric acid. This adds water molecule into the polymer.
 Water molecules break apart the peptide links of the protein molecule, leaving
separate amino acid molecules.
 The hydrolysis is the opposite of condensation polymerisation.

 Given the structure of a protein molecule, the structures of the amino acids used
to form it can be shown by simply breaking every peptide link to leave amine and
carboxyl groups.

Hydrolysis of proteins during digestion

 During digestion, enzymes by hydrolysis break down the proteins we eat into
amino acids.
 These amino acids are transported around the body by blood. In the bloodstream
during assimilation, condensation reactions build the amino acids up to produce
proteins required by the body.

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