ORGANIC CHEMISTRY

Organic chemistry is the study of carbon compounds.

Carbon compounds are also called organic compounds
Carbon forms 4 covalent bonds (tetravalent) as a result it forms;
 Straight chain compounds
 Branched chain compounds
 Cyclic or ringed compounds
Exampls:

This molecule has a chain of here 5 carbon atoms 5 carbon atoms formed
5 carbon atoms. Form a branched chain a ring.
In the examples above, the compounds contain carbon and hydrogen only. A compound that
contains carbon and hydrogen atoms only is called a hydrocarbon.
Carbon compounds are divided in to groups or families and each family is called a homologous
series

HOMOLOGOUS SERIES
A homologous series is a group of compound that have;
 The same name ending
 Similar physical and chemical properties
 Differ by a -CH2 in their formula

In this topic we will study only 4 groups ( 4 homologous series)

 Alkanes
 Alkenes
 Alkanols, also known as alcohols
 Alkanoic acids, also known as organic acids or carboxylic acids
NAMING ORGANIC COMPOUNDS
The name of an organic compound is determined by two things:
1. The homologous group it belongs to.
All compounds in the same homologous series have the same name ending(suffix) and each
group has a specific suffix.
Homologous series Name ending (suffix)
Alkane -ane
Alkene -ene
Alkanol -anol or -ol
Alkanoic acid -anoic acid

2. The number of carbon atoms in the chain i.e the length of its carbon chain.
The number of carbon atoms in the chain determines the first part of the name (prefix)
The no of carbons The name prefix
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-

ALKANES
 These are hydrocarbons characterized by having single covalent bonds.
Single C-C bonds and single C-H bonds. Because of this, alkanes are referred to as
saturated hydrocarbons
 Alkanes have a general formula CnH2n+2 where n is the number of carbon atoms in the
compound, and they all have the suffix -ane in their names.
 Have a suffix -ane in their names.
Examples of alkanes
No of carbons prefix suffix name Structural formula
1 Meth- -ane Methane

2 Eth- -ane Ethane

3 Prop- -ane propane

4 But- -ane Butane

5 Pent- -ane Pentane

Some alkanes and their physical properties

NAME Molecular Melting Boiling point Physical Mr
formula point ⁰C ⁰C state
Methane CH4 -182 -161 Gas 16
Ethane C2H6 -183 -88 Gas 30
Propane C3H8 -188 -42 Gas 44
Butane C4H10 -138 -0.5 Gas 58
Pentane C5H12 -130 36 Liquid 72
.
.
.Decane C10H22 -30 174 Liquid 142
Eicosane C20H42 37 344 solid 282

ISOMERISM IN ALKANES
Isomers are two or more organic compounds with the same molecular formula but different
structures.
Example;

The two above are isomers, the both have the molecular formula C4H10
Naming branched organic compounds
- Identify the homologous group
- Identify the longest carbon chain
 These 2 gives the parent name

- Identify the name of the branch

- Number of carbons starting from the end where the branch is closest to.
 These 2 gives rest of the name

Note; As the number of carbon atoms increase, the number of possible isomers also increases.
e.g.

 More branching = low boiling point and melting points

SOURCES OF ALKANES
Natural gas and petroleum are the two main sources of alkanes.
Petroleum is a mixture of complex alkanes, therefore alkanes are obtained from petroleum by
fractional distillation. Fractions with the lowest boiling points are collected at the top while
those with the highest boiling points are collected at the bottom.
Note: the longer the carbon chain, the higher the boiling point.

FRACTION USE
Refinery gas Bottled gas as a fuel for domestic heating and
cooking
Gasoline/petrol Fuel for cars
Naphtha Used to make chemicals
Kerosene/Paraffin Jet fuel, paraffin for heating(stoves) and
lighting(lamps)
Diesel oil Fuel for diesel engines,
Lubricating oil Oil for cars and other machines
Fuel oil Fuel for ships and power stations
 Bitumen/ asphalt For making roads and roofs

CHEMICAL PROPERTIES OF ALKANES

The alkanes undergo two notable reactions only:
i. Combustion reactions
ii. Substitution reactions

i. Combustin is burning. This is the most important chemical reaction of the alkanes.
 In a good supply of air, the alkanes will burn producing carbon dioxide and water

C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g)

 With a limited supply of oxygen or air, alkanes burn giving out carbon monoxide gas.

2C3H8(g) + 7O2(g) 6CO(g) + 8H2O(g)

ii. Substitution is replacement. Another reaction of the alkanes is substitution rection. The
reaction takes place in the presence of the ultraviolet light. This is exemplified in the reaction of
methane with chlorine below

CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)

In this reaction, one hydrogen atom has been substituted by one chlorine atom to form
chloromethane (CH3Cl) and hydrogen chloride. The reaction is a chain reaction which continues
until all hydrogen atoms have been substituted giving rise to a number of products.

CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)

CH3Cl(g) + Cl2(g) CH2Cl2(g) + HCl(g)
CH2Cl2(g) + Cl2(g) CHCl3(g) + HCl(g)
CHCl3(g) + Cl2(g) CCl4(g) + HCl(g)

The products are :

CH3Cl(g chloromethane
CH2Cl2(g) dichloromethane
CHCl3(g) trichloromethane
CCl4(g) tetrachloromethane or carbon tetrachloride

ALKENES

 They are characterised by a covalent carbon to carbon double bond C=C in their
structures. Because of the double bond they posses, alkenes are said to be
unsaturated.
 Alkenes have a general formula CnH2n , wherev n is the number of carbon atoms.
 Have a suffix -ene in their names.

* Most alkenes are gases or liquids of low boiling points at room temperature and pressure. The
first 3 alkenes are gases, the next 14 are liquids and the rest are solids.

Examples
Alkene Molecular Formula Structural Formula
Ethene C2H4

Propene C3H6

Butene C4H8

NOTE:
 The double bond can be situated between any 2 carbons in the chain, and the names
differ.
 There can be more than one double bond in a compound, the names also differ.
SOURCES OF ALKENES
Alkenes are manufactured from alkanes by a process called cracking (breaking). In this process,
a long chain of an alkane is cracked to give an alkene and a shorter alkane. This is achieved by
using high pressures and temperatures without a catalyst, or lower temperatures and pressure in
the presence of a catalyst.

There are two types of cracking:

1. Catalytic cracking
A catalyst is used or added, mixture of silicon dioxide and aluminium oxide (zeolites). Alkanes
are heated at low temperatures (500⁰C) and low pressures (1 atm)

2. Thermal cracking
In thermal cracking, long chain molecules are heated to high temperatures (about 750⁰C) and
compressed to high pressure (about 70 atmospheres)

Cracking is important for two reasons:

 It turns long chain molecules in to more useful shorter ones. E.g. naptha can be cracked
to get right molecules for making petrol.
 Produce short chain compounds like ethene with a double bond, so these are reactive and
can be used to make plastics and other useful products.

CHEMICAL PROPERTIES OF ALKENES

1. Combustion reaction
Alkenes burn in air producing carbon dioxide and water when there is adequate supply of
oxygen.
C2H4(g) + 3O2(g) 2CO2(g) + 2H2O(g)
With inadequate or limitedsupply of air/oxygen, the burning produces carbon monoxide and
water
C2H4(g) + 2O2(g) 2CO(g) + 2H2O(g)

2. Addition reaction
Alkenes undergo addition reaction due to their unsaturation

a) Reaction with steam (hydration)

Alkenes react with steam forming alcohols. A molecule of steam(water) will add across the
double covalent bonds in ethene to form ethanol. A catalyst of phosphoric acid (H3PO4) is
employed and a temperature of 300⁰C under a pressure of 60-70 atms.
phosphoric acid
Alkene + Steam 0 Alcohol
300 C , 70 atm
k e.g. C2H4(g) + H2O(g) C2H5OH
Ethene Steam Ethanol

If the reaction is with propene, the resulting alcohol will be propanol, butene will be butanol,
pentene will be pentanol etc.

b) Reaction with hydrogen (hydrogenation)

Alkenes react with hydrogen in the presence of a finely divided metal catalyst such as
Nickel(Ni), or Palladium (Pd) , or Platinum (Pt), or Rhodium (Rh), at a temperature of
about 150⁰C.
¿/, Pt /, Pd
Alkene + Hydrogen Alkane
150⁰ C
C2H4(g) + H2(g) Ni C2H6
150⁰C
 If the reaction is with propene, the resulting alkane will be propane, butene will be butane,
pentene will be pentane. The reaction of alkenes with hydrogen to form alkanes is used in
industry to produce margarine.

c) Reaction with bromine (Halogenation)

Alkenes will react with bromine or the halogens formimg haloalkane products.
Ethene reacts with bromine forming 1,2-dibromoethane. The brown colour of bromine is
decolourised in the process.
C2H4(g) + Br2(g) C2H4Br2(l)
Ethene bromine 1,2 -dibromoethane
The bromine adds across the double bond.

3. Polymerisation Reaction
Is another very important reaction the alkenes undergo due to their unsaturation (possession of a
double bond).
In this reaction, several alkenes (ethene , for instance) will react with itself forming a large
molecule called a polymer. The individualunits that react together are called monomers.
Monomer + monomer Polymer

TEST FOR ALKENES

Alkenes are tested by reacting with bromine solution.
When an alkene is reacted with bromine solution, the bromine solution is decolourised
Uses of Alkenes
 Used in the provision of heat energy
 Used in industry in the manufacture of alcohols
 Used as industrial solvents.
ALKANOLS
-Are commonly known as alcohols.
- have a functional group known as hydroxyl group(-OH) in their formula
NOTE; In the formula of an alkane, one hydrogen is replaced by the hydroxyl group to form an
alkanol
-The general formula is CnH2n + 1OH
-miscible with water

Examples
Alkanol Molecular Mr B.pt Structural formula
formula ⁰C
Methanol CH3OH 32 64

Ethanol C2H5OH 46 78

Propanol C3H7OH 60 97

Butanol C4H9OH 74 117

Pentanol C5H11OH 88

SOURCES OF ALKANOLS
Ethanol is the most important of the alcohols. It can be obtained by:
i) catalytic addition of steam to ethene
ethene + Steam catalyst ethanol

ii) fermentation of glucose or starch

Glucose yeast Ethanol + carbon dioxide
C6H12O6 yeast 2 C2H5OH + 2CO2
40⁰C
Fermentation is the process employed to break down carbohydrates by an enzyme under
anaerobic conditions. Fermentation is used to break down glucose or starch to produce the
alcohol, ethanol and carbon dioxide by the action of enzyme zymase secreted by yeast.

Many other kinds of fermentation occur naturally, Lactase, an enzyme produced by bacteria in
milk causes milk to sour by changing lactose (milk sugar) in to lactic acid.
Fermentation takes place at an optimum temperature of 40⁰C
C6H12O6 yeast (zymase) 2 C2H5OH + 2CO2
40⁰C
CHEMICAL PROPERTIES OF ALKANOLS
1. Combustion of alcohols
Alcohols are able to burn in air or oxygen forming carbon dioxide gas, (CO2) and steam with
adequate supply of oxygen. With inadequate supply of oxygen, carbon monoxide and steam are
formed.
e.g. C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(g)
ethanol + Oxygen carbondioxide + water

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

Carbon monoxide + water
2. Oxidattion of alcohols
Alcohols are able to undergo oxidation reaction (addition of oxygen) to their molecule.
When an alcohol is oxidized it forms an alkanoic acid. The oxidizing agent in this reaction is
acidified potassium dichromate. The potassium dichromate is acidified with dilute sulphuric
acid.
When ethanol undergoes oxidation, ethanoic acid is formed.
Ethanol + Oxygen Ethanoic acid + water
CH3CH2OH(l) + 2(O)(g) CH3COOH(l) + H2O(l)
Ethanol is also oxidized by atmospheric oxygen to form ethanoic acid(vinegar). If you leave your
beer overnight, it becomes very acidic or stale, that is ethanoic acid(vinegar).

OTHER CHEMICAL PROPERTIES

3. Dehydration of alcohols
When an alcohol looses a water molecule (dehydration), it forms the corresponding alkene.
When ethanol is dehydrated it forms ethene and butanol is dehydrated to form butene.
To dehydrate alcohols, the alcohol is heated with a catalyst such as aluminium oxide or
phosphoric acid. A dehydrating agent such as sulphuric acid could also be used to dehydrate an
alcohol.
e.g.
Ethanol Ethene + Water
C2H5OH catalyst/heat C2H4 + H2O

4. Esterification reaction
Esterification is a reaction similar to neutralization reaction (acid + alkali). In esterification
reaction, an organic acid reacts with an alcohol in presence of concentrated sulphuric acid as a
catalyst to form an organic salt (called an ester) and water.
Alcohol + Alkanoic acid Ester + water
Ethanol + ethanoic acid ethylethanoate + water
C2H5OH + CH3COOH conc. H2SO4 C2H5COOCH3 + H2O
USES OF ETHANOL
 In making alcohol beverages such as wine
 In the preparation of medicine
 iAs food preservative
 In industries as solvent
 As a fuel in place of petrol in some countries

ALKANOIC ACIDS
-Are organic acids also known as carboxylic acids
-Same name ending -anoic acid
-have the functional group ( -COOH) in their structure.
- General formula CnH2n+1COOH, but sometimes CnH2nO2 is used
Example
Name Molecular formula Molecular mass Structural formula
Methanoic acid HCOOH 46

Ethanoic acid CH3COOH 60

Propanoic acid C2H5COOH 74

 Butanoic acid C3H7COOH 88

Pentanoic acid C4H9COOH 102

SOURCES OF ALKANOIC ACIDS

 Are obtained from plant sources
-Tartaric acid is obtained from grapes
-citric acid is obtained from citrus frits
-ascorbic acid is also obtained from fruits
-vinegar(ethanoic acid) is obtained from vines and from ethanol

 Can be made from natural gas. Methane is used to manufacture methanol, which is then
reacted with carbon monoxide to obtain ethanoic acid.

Methanol + carbon monoxide ethanoic acid

CH3OH + CO CH3COOH

 Can also be obtained from alkenes. Ethene is reacted with oxygen in the presence of a
catalyst to obtain an intermediate compound (ethanal), which is then converted to
ethanoic acid by reacting with more oxygen.

2C2H4 + O2 2CH3CHO + O2 2CH3COOH

Ethanoic acid can be prepared in the laboratory by the oxidation of ethanol with oxidizing
agents such as acidified potassium dichromate and acidified potassium manganate (VII)
solution. With acidified potassium dichromate (K2Cr2O7), ethanoic acid and water are formed
while the colour of the potassium dichromate changes from yellow to green. With acidified
potassium manganate (VII) (KMnO4), the deep purple colour of the potassium mamganate (VII)
is decolourised.
Ethanol + Oxidising agent ethanoic acid + water
PHYSICAL PROPERTIES OF ETHANOIC ACID (VINEGAR)
 A colourless liquid
 It is a weak acid
 Has a sour taste
 Has a strong irritating smell (pungent smell)
 Completely miscible with water

CHEMICAL PROPERTIES OF ETHANOIC ACID

 Acidity
- is a weak acid
- dissolves in water and partially ionizes
-turns blue litmus paper red
-react with alkalis or bases to form salt and water(neutralization), salt formed is an
ethanoate
-reacts with carbonates to form carbon dioxide
-reacts with reactive metals giving off hydrogen gas. With sodium metal, sodium
ethanoate and hydrogen gas are formed.

 Reaction with alkanols

React with ethanol to form ethylethanoate and water. This reaction is called esterification
reaction. Ethylethanoate is an organic compound called an ester.