ORGANIC CHEMISTRY

O LEVEL MODULE

COMPILED BY NC NYIKA
WHAT IS ORGANIC CHEMISTRY?
- It is the study of carbon containing compounds excluding substances like
carbon monoxide, carbon dioxide, carbonates
- Carbon is the only element able to form millions of different compounds.
Why is carbon able to form so many compounds?
i) It has 4 electrons in its outermost shell and can use these electrons to
bond covalently to different kinds of atoms.
ii) its atoms are able to form chains. This property is called catenation.
- Since there are too many organic compounds it is very difficult to study
each compound separately. To make it easy to study organic compounds
they are placed into groups of compounds with similar chemical properties.
These groups are called homologous series.
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Homologous series
- A homologous series is a family of compounds with the same general formula and similar
chemical properties.
Examples of homologous series
i) Alkanes
ii) Alkenes
iii) Alcohols
iv) Carboxylic acids
v) Amines
Functional groups
- Each of the above groups except alkanes has a special group of atoms which determines
its chemical properties.
- A functional group is an atom or group of atoms that gives a compound its characteristic
properties.
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Homologous series and their functional
groups
Homologous series Functional group
alkene C=C
alcohol -OH
Carboxylic acids -COOH
amines -NH₂
HYDROCARBONS
- Hydrocarbons are compounds made of hydrogen and carbon only.
- The most common hydrocarbons are (i) alkanes
(ii) alkenes
- Hydrocarbons are classified based on weather they have single, double or triple bonds.
- The most important source of hydrocarbons are natural gas and petroleum(crude oil).
- Many useful products can be produced using hydrocarbons. eg plastics, refrigerants, detergents,
pesticides, food preservatives
ALKANES
-these are hydrocarbons that have single bonds only.
-they are also known as saturated hydrocarbons.
-some have straight chains while others have branched carbon chains.
-naming of alkanes is usually based on the number of carbon atoms in each molecule.
-the general formula of is CnH₂n₊₂
Naming and molecular structures of organic
compounds
- Each carbon atom should have 4 covalent bonds around it ie 4 single bonds or one double bond and 2 single bonds.
- Each single bond is represented using a single line eg C-H between the atoms and a double bond by two lines eg C=C.
- Names of all organic compounds whose molecules have one carbon atom start with meth-
2 carbons- eth-
3 carbons- prop-
4 carbons- but-
5 carbons- pent-
6 carbons- hex-
- the last part of each name indicates the homologous series to which the compound belongs.
eg –ane for alkane
-ene for alkenes
-ol for alcohols
-oic acid for carboxylic acids

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Structure and naming of alkanes
Change in physical properties of
alkanes as molecular mass increases
- the first four alkanes ie methane, ethane, propane and butane have low
melting and boiling points and exist as gases at room temperature and
pressure.
- As the molecular mass increases from pentane(C₅H₁₂) to heptadecane
(C₁₇H₃₆) the melting and boiling points continue to increase and all alkanes
having 5 carbons to 17 carbons are liquids at room temperature and
pressure.
- All alkane having 18 carbons or more are solids at room temperature and
pressure.
- Methane has the lowest density of all alkanes ie 0.00068g/cmᶾ. As the
molecular mass increases the density also increases. Octadecane has a
density of 0.7g/cmᶾ
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Physical properties of alkanes

Name Molecular formula mp(˚C) Bp(˚C) State at rtp

methane CH₄ -182 -162 gas
ethane C₂H₆ -172 -89 gas
propane C₃H₈ -187 -42 gas
butane C₄H₁₀ -138 -0.5 gas
pantane C₅H₁₂ -130 36 liquid
heptadecane C₁₇H₃₆ 22 292 liquid
octadecane C₁₈H₃₈ 28 308 solid
Structural Isomerism
Chemical properties of alkanes
- Alkanes are generally unreactive with most substances because they are saturated.
- However they undergo some reactions such as
(i) Combustion
- combustion means burning. Most alkanes easily burn in presence of oxygen giving out heat. That is the reason why they are used as
fuels.eg
methane + oxygen → carbon dioxide + water
CH₄ + 2O₂ → CO₂ + 2H₂O
butane + oxygen → carbon dioxide +water
C₄H₁₀ + ¹ᶾ/₂O₂ → 4CO₂ + 5H₂O
- This kind of combustion that gives out carbon dioxide is called complete combustion. It occurs when there is plenty of oxygen. It gives out
more energy than during incomplete combustion.
- Incomplete combustion takes place when a fuel burns in a limited supply of oxygen. It gives out carbon monoxide and water. Less energy is
given out. Apart from the carbon monoxide and water incomplete combustion also produces soot ( unburnt carbon particles)
methane + limited oxygen → carbon monoxide + water

2CH₄ + 3O₂ → 2 CO + 4H₂O

- during complete combustion a blue flame is produced while during incomplete combustion the flame is orange
(ii) Reaction with chlorine

- When an alkane and chlorine gas are mixed in the dark, no reaction will take place.
- However if the alkane- chlorine mixture is exposed to UV light it reacts very fast producing a mixture of products.
- Reactions that take place only when the reactants are exposed to light are called photochemical reactions.
- In this reaction the energy in UV light is used to break down the chlorine molecules to produce free radical chlorine atoms. A free
radical is an atom or group of atoms with unpaired electrons.
Cl-Cl ᶸᵛ→ Cl + Cl
- Free radicals are very reactive therefore the chlorine free radicals will react with the alkane molecules by substitution reaction
whereby the chlorine atoms replace hydrogen atoms on the alkane molecules. eg reaction between methane and chlorine gas can
produce a mixture of 4 products due to substitution of one, two, three or all hydrogens on methane molecules

- If two hydrogens are substituted, dichloromethane (CH₂Cl₂) is formed.

EXERCISE
(i) Draw the structural formula of dichloromethane
(ii) Suggest a name and structure of the molecule formed when 3 hydrogen atoms of methane molecule are substituted.

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ALKENES
What are alkenes?
- This is a homologous series of unsaturated hydrocarbons containing double C=C bonds.
- They are called unsaturated because it is possible to break one of the double bonds and add another kind of
atom.
- They have the general formula CnH₂n
- Their names end with –ene and are general more reactive than alkanes because of the double bond.
- The first 3 members of the series are ethene, propene and butene. These are all gases at rtp
Importance of ethene
- Ethene is the most important alkene because it has several important uses including
- (i) making ethanol
(ii) making ethanoic acid (vinegar)
(iii)making plastics such as polythene
Where do we get alkenes?
-very few alkenes are obtained naturally. Most alkenes are produced from alkanes by a process called cracking.
-cracking is a process that involves breaking large molecules of alkanes into a smaller alkane and an alkene.
Large alkane → smaller alkane + alkene eg
Dodecane → decane + ethane
C₁₂H₂₆ → C₁₀H₂₂ + C₂H₄
How is cracking done?
(i) Catalytic cracking
- it involves cracking by passing an alkane over a mixture of aluminium oxide and chromium oxide catalyst heated to about
500˚C.
(ii) Thermal cracking
- it involves heating the alkane to high temperature of about 800˚C without using a catalyst.
Alkane cracking in the laboratory
- The set up below is used to crack alkanes in the laboratory.
- The alkene is collected over water because it is insoluble in water.
- The catalyst is placed in such a position that the heated paraffin vapour passes over the hot catalyst.
Reactions of alkenes
-alkenes are more reactive than alkanes because of the double bond.
- They undergo several types of reactions including
(i) addition reactions
(ii) combustion
(iii) polymerization
Combustion reactions
-alkenes undergo combustion producing carbon dioxide and water.
Write a balanced equation for the combustion of the following alkenes
(a)ethene (C₂H₄)
(b)propene (C₃H₆)
Addition reactions
- Addition reactions are reactions in which two or more molecules join to form a single product.
- Alkenes can undergo addition reactions with (i) hydrogen - hydrogenation
(ii) halogens - halogenation
(iii) water - hydration .
 Addition of hydrogen
- Alkenes react with hydrogen in a process called hydrogenation forming alkanes.
- Reaction occurs in the presence of nickel catalyst at 200˚C. eg reaction of ethene with
hydrogen produces ethane.

- Hydrogenation is used to change vegetable oils into margarine.

Addition of bromine
-when an aqueous solution of bromine (bromine water) is added and shaken with an
unsaturated hydrocarbon the bromine water will be decolourised ie it will lose its reddish –
brown color.
-the bromine adds to the C=C bond of the alkene molecule. eg reaction of ethane with
bromine water.
-this reaction is used as a test for unsaturation.
Addition of water
- Addition of water molecule to another molecule is called hydration.
- Alkenes react with steam to produce alcohols. eg Ethene reacts with steam to produce ethanol. The reaction
is carried out at a temperature of 300˚C and 60-70 atm, with phosphoric (V) acid as catalyst

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ALCOHOLS
WHAT ARE ALCOHOLS?
- homologous series of compounds with the general formula CnH2n+1OH.
- The molecules have the functional group – OH (hydroxyl group)
- Their names end with –ol.
STRUCTURAL FORMULAE AND MOLECULAR FORMULAE OF THE FIRST 4 ALCOHOLS

CH₃OH C₂H₅OH C₃H₇OH C₄H₉OH

(CH₃CH₂OH) (CH₃CH₂CH₂OH) (CH₃CH₂CH₂CH₂OH)
-the formula of each alcohol differs from the previous one by an extra –CH₂- group
- The most common alcohol is ethanol.

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Ethanol
How do we manufacture ethanol?
1.By reacting ethane with steam
2.By fermentation of sugars with yeast
Preparation of ethanol by fermentation
-fermentation is a chemical reaction in which sugars are broken down into smaller molecules (eg ethanol) by microorganisms
in absence of oxygen.
-in ethanol production sugars found in foods like fruits, wheat, potatoes, maize and barley are broken down by enzymes
produced by yeast to ethanol and carbon dioxide.
NB: Yeast is a kind of fungus
-one kind of sugar is glucose (C₆H₁₂O₆)
Fermentation of glucose
.
-the yeast and glucose solution are mixed and left for one or more days in a
warm place.
-the carbon dioxide can be tested using
limewater. Limewater turns milk in the
presence of carbon dioxide.
- the water used in the experiment is first
boiled to kill any microorganisms that may
be found in the water that may affect yeast
growth.
- The water is allowed to cool before yeast is added to avoid killing of yeast
by high temperature
Uses of ethanol
(i) As a solvent
- ethanol is a good solvent. It is able to dissolve many organic
substances that are not soluble in water.
- it is used as a solvent in cough medicines, paints, perfumes and deodorants.
(ii) As a fuel
- ethanol can be mixed with petrol to make blend fuel. eg E10 is a
fuel containing 10% ethanol and 80% petrol.
- blending reduces the amount of foreign currency used to buy petrol.
- ethanol burns in air giving out carbon dioxide and water
(iii) Alcoholic beverages
- used in beer and wine
- however use of alcoholic beverages can lead to social problems such as violence, traffic accidents, spread of STDs
(iii) Making ethanoic acid
- used to make vinegar (ethanoic acid) which is used to preserve food and make esters.

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CHEMICAL REACTIONS OF ETHANOL
- Ethanol can undergo several types of chemical reactions including
(i) combustion
(ii) oxidation
(iii)dehydration
(iv)esterification
COMBUSTION
- Ethanol burns in oxygen giving out carbon dioxide and water.
- As a result ethanol is used in spirit burners and as blend fuel.
- Advantages of using ethanol are that it is less polluting and cheap.
Exercise
Write a balanced equation for the complete combustion of ethanol (C₂H₅OH).
Oxidation of ethanol
- When an ethanol molecule is oxidized, it loses two hydrogen atoms and gains one oxygen atom.
- potassium dichromate is orange in colour. When it is used to oxidise ethanol it changes colour from orange to dark green.
Ethanol can be oxidized to ethanoic acid (an organic acid) by reacting it with a strong oxidizing agent such as acidified
potassium dichromate (VI) or potassium permanganate (VII).
- This reaction can be used to test for alcohol.
- The ethanol can also be oxidized by oxygen in air. This causes wines to develop a sour taste and a vinegar like smell if left
exposed to air for a long time.
Dehydration of ethanol
- Dehydration reaction of ethanol is the opposite of hydration of ethene.
- It produces ethene by removal of H₂O from a molecule of ethanol.
ethene →hydration →ethanol
ethanol → dehydration → ethene
Write a balanced equation for the dehydration of ethanol.
CARBOXYLIC ACID
What are carboxylic acids?
-this is a homologous series of organic acids with the functional group
-COOH which can also be written as -CO₂H.
- They have the general formula CnH₂n₊₁COOH.
- Their names end with –oic acid.
- They are weak acids ie they dissociate slightly in water.
- The first four carboxylic acids are methanoic acid, ethanoic acid, propanoic acid and butanoic acid.

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Structural and molecular formulae of
carboxylic acids
Methanoic acid ethanoic acid propanoic acid butanoic acid

-The most important carboxylic acid is ethanoic acid also known as acetic acid. It is commonly called vinegar.
- Large amounts of ethanoic acid are used as flavouring and as a preservative.
- In the laboratory ethanioc acid is mainly prepared by the oxidation of ethanol using an acidified oxidizing agent such as
potassium dichromate (VI) or potassium permanganate (VII).
- However industrially vinegar is made by mainly by oxidation of ethanol in air. This is done by enzymes in bacteria.

CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS

- All carboxylic acids react in the same way as other acids ie reactions with bases forming a salt and water. Reaction with
metals forming salt and hydrogen. Reaction with carbonates forming salt, water and carbon dioxide
Esterification
- It is the reaction between an alcohol and a carboxylic acid .
- The product is called an ester.
- For example the reaction between ethanoic acid and propanol

- This is a kind of condensation reaction in which two molecules combine with the elimination of a water molecule.
- The strong, sweet smell of bananas, pineapples and other fruits are due to presence of one or more esters.
- Chemists make synthetic esters used as fruity flavors for foods such as ice creams, chewing gums, sweets, yoghurts cakes and in
perfumes.
- Esters are also used as solvents for organic compounds and have low boiling points. Therefore esters are used as solvents for glues,
perfumes, nail polish removers and paints.
- Vegetable oils are also a special kind of esters called polyesters.
Structures and names of some esters
SOAPS
What is a soap?
- A soap is a salt of long chain carboxylic acids.
- Long chain carboxylic acids are also called fatty acids. These have carbon chains that are usually made of 17 or more
carbon atoms.
- Fatty acids can be produced from natural fats and oils from plants or animals.
- Fats and oils are esters of fatty acids and an alcohol that has three -OH groups called glycerol

- Structure of glycerol

- Each of the –OH groups will be combined with a fatty acid by condensation reaction resulting in a large molecule with 3
ester linkages called a fat or oil.

- Structure of fats an oils

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Soap manufacturing
- Soap is manufactured using fats or oils.
- Fats and oils are boiled in water so as to break the ester linkages by adding water molecules. The breaking of
molecules by adding water is called hydrolysis.
- Each fat/oil molecule breaks into 3 fatty acids and one glycerol molecule on boiling.
- In practice the fats are boiled in the presence of a strong alkali such as sodium hydroxide or potassium
hydroxide so that the fatty acids are neutralized as soon as they are formed. This type of reaction is called
saponification. eg
- fat + strong alkali → soap(salt) + glycerol
Soap structure and action
Structure of soap

- A soap molecule is made up of two parts which are

(i) hydrocarbon chain eg(C₁₇H₃₅) also known as the ‘tail’ – this part
does not dissolve in water because it is covalent and it is described as
hydrophobic (water hating).
(ii) ionic ‘head’ eg(COO⁻Na⁺) – this part dissolves in water because it is
ionic and is described as hydrophilic (water loving).

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Soap action