Alkanes
This is the simplest honmologous series
General formula: CnH2n where n≥1
Examples
Molecular Structural Names
Formula Formulae
H
CH4 Methane
C
H H
H H
C C
C2H4 H H Ethane
H H
H H H
C C C
C3H8 H H Propane
H H H
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H H H H
H C C C C H Butane
H H H H
H
C4 10
H H
H C C C H
2-methylpropane
H H
C
H H
Compounds that
contain the same molecular formula but different structural formulae like butane and 2-
methylpropane are called isomers.
Definitions.
Isomerism is the existence of compound with the same molecular formulae but different
arrangement of atoms in a compound.
Types of isomerism
1. Structural isomerism
2. Optical isomerism
Structural isomerism
Here compounds differ in arrangement of atoms in a compound.
(a) Chain isomerism: compound have the same molecular formula but different arrangement of
atoms in the chain.
(i) Structure isomers:
These are common to alkanes, isomers differ in arrangement of atoms in the chain
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Examples
H H H H
C C C C
H H Butane
H H H H
C4H10
H H H
H C C C H
H H
C
H H
H 2-methylpropane
(ii) Functional isomerism
Compounds have the same molecular formula but different functional groups such
as alcohols and ether.
Example
H H
C O C
H H Dimethylether
H H
H H
C C
H OH Ethanol
H H
3
(iii) Positional Isomer:
The isomers have the same molecular formula, same functional group but
different positions of the functional group on a molecule. Examples
CH3CH2CH=CH2 but-1ene CH3CH=CHCH3
but-2-ene
(b) Stereo isomerism
Compounds have the same molecular formula, the same functional group but different
arrangement of atoms in space.
(i) Geometrial isomerim: atoms, molecules are arranged differently about a double
bonds:
Example
CH3 CH3
C C
H H Cis but-2-ene
H
CH3
C C
Trans but-2-ne
CH3
H
(ii) Optical isomers:
Compounds have the same molecular formula, the same
functional group but differ in optical properties towards plane polarised light.
Those that rotate light towards the right are called dextro isomers and those that
rotate light towards the left are called levo isomers.
Nomenclature
(a) Straight chain isomers
Straight chain isomers are named according to the number of carbon atoms in the chain.
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The names of the first ten straight chain isomers are given below;p
CH4 Methnane
CH3CH3 Ethane
CCHH33CCHH22CCHH23C PBruotpaannee
CCHH33CCHH22CCHH22CCHH22CCHH32C H 3
PHeenxtaannee
CH3CH2CH2CH2CH2CH2CH3 Heptane
CH3CH2CH2CH2CH2CH2CH2CH3 Octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 Nonane
CH3CH3CH3CH3CH2CH2CH2CH2CHCH3 Decane
An alkyl group is an alkane less
one hydrogen atom. Example
CH4 Methane CH3- methyl group
CH3CH3 Ethyl CH3CH2- Ethyl group
CH3CH2CH3 Propane CH3CH2CH2- Propyl group
CH3CH2CH2CH3 Butane CH3CH2CH2CH2- Butyl group
Because alkyl group do not have chemical properties, they are generally represented by a letter
R,
(a) Naming branched alkanes
(i) Determine the number of carbon atoms in the longest carbon chain that contain the
branch.
(ii) Number the carbon atoms from the side nearest the branch. Example
4 3 2 1
CH3CH2CHCH2 2-Methylbutane
CH3
(iii) If there more than one similar alkyl groups on the longest chain; use di, tri, tetra to
indicate the number of such groups on the main cahin.
Example.
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CH3 CH3
CH3 CH CH CH2 CH3 2,3-dimethylpentane
1 2 3 4 5
Note that
• This name implies that there is a methyl goup attached to carbon 2 and another to carbon
3 of the pentane.
• When writing the name of organic compound, a coma (,) is placed between figures and a
dash (-) between a figure and a letter.
(iv) If different branches name them alphabetically
CH2CH3
2
CH3CHCHCH2CH3 3-Ethyl-2-methypentane
13 4 5
CH3
Note that
“E” for ethyl group comes before “M” for methyl group in the alphabets.
(v) If branching occurs equal distance from either side, choose a name that gives the least
sum of combination of numbers.
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Example
CH3
CH3
CH3 C CHCH3
1 2 3 4
CH3
2,2,3-Trimethylbutane AND NOT 2,3,3-Triethylbutane
sum = 7 sum = 8
2,2,3-trimethylbutane is the correct name because it gives the least sum for the combination
of numbers. Exercise
Name the following compounds
(a) CH3CH2CH2CH2CH2CH3 (b) CH3CHCH3CH2CH3
CH3
CH3
(b) CH3CH2CHCH2CH3 (d) CH3CHCHCH3
CH3 CH3
CH3
(e) CH3 C CH3
CH3
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Solution
(a) CH3CH2CH2CH2CH2CH3 (b) CH3CHCH3CH2CH3 2-methylpentane
CH3
Hexane
CH3
(b) CH3CH2CHCH2CH3 (d) CH3CHCHCH3 2,3-dimethylbutane
CH3 CH3
3-methylpentane
CH3
(e) CH3 C CH3 2,2-dimethypropane
CH3
Physical properties of alkane
- they are insoluble in water
- they are soluble in organic solvents
- they range from gases to liquids to waxy solides
Chemical properties
1. They burn in air to produce carbon dioxide, water and heat. Due to production of heat they
are used as fuel.
Example
CH4 + 2O2 CO2 + 2H2O + heat
2. Chlorination: they react with chlorine in presence of sunlight or u.v-light to produce
chlorinated alkanes.
Example
CH4 + Cl2 may give CH3Cl chloromethane
CH2Cl2 dichloromethane
CHCl3 trichloromethane
CCl4 tetrachloromethane
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Mechanism
A mechanism are steps followed by a reaction from the reactant to the products.
The following are steps followed in chlorination of methane
1. Chlorine molecules dissociates into atoms with unpaired electron. Atoms or molecules
with unpaired electron are called free radicals. Free radicals are indicated by a dot on the
atom that posses un paired electron
Cl Cl 2Cl
2. Chlorine radical attacks a methane to produce hydrogen chloride and a methyl radical.
H H
C H Cl H C
H + HCl
H H
Methyl radical
3. Methyl radical reacts with a chlorine molecule to form chloromethane and a chlorine
radical
H H
C + Cl Cl H C
H Cl + Cl
H H
chloromethane
4. Chlorine radical attacks a chloromethane to produce hydrogen chloride and a
chloromethyl radical.
Cl Cl
C H Cl H C
H + HCl
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H H
Chloromethyl radical
5. Chloromethyl radical reacts with a chlorine molecule to form dichloromethane and a
chlorine radical
Cl Cl
C + Cl Cl H C
H Cl + Cl
H H
Chloromethyl radical dichloromethane
6. Chlorine radical attacks a dichloromethane to produce hydrogen chloride and a
dichloromethyl radical.
Cl Cl
C H Cl Cl C
Cl + HCl
H H
Dichloromethane dichloromethyl radical
7. Dichloromethyl radical reacts with a chlorine molecule to form trichloromethane and a
chlorine radical
Cl Cl
C + Cl Cl Cl C
Cl Cl + Cl
H H
Dichloromethane trichloromethane
8. Chlorine radical attacks a trichloromethane to produce hydrochloride and a
trichloromethyl radical.
Cl Cl
C H Cl Cl C
Cl + HCl
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Cl Cl
Trichloromethane Trichloromethyl radical
9. Trichloromethyl radical reacts with a chlorine molecule to form tetrachloromethane and a
chlorine radical
Cl Cl
C + Cl Cl Cl C
Cl Cl + Cl
Cl Cl
Trichloromethyl radical teterachloromethane
Terminating steps
Meamwhile the radicals may combine to produce molecules. The reactions where radicals react
to produce molecules is called terminating steps i.e, they prevent the reaction from continuing.
Some of the terminating steps are:-
1. Chlorine radical + chlorine radical produces chlorine molecule
Cl + C l Cl2
2. Methyl radical + methyl radical produces ethane
H3C + CH3 CH3CH3
3. Methyl radical reacts with chlorine radical to form chloromethane and so on.
H3C + Cl CH3Cl
Sources of alkanes
1. Petroleum product
2. Biogas
Biogas is prduced by anaerobic decomposition of organic matter (such as cow dung, plant
remains, faeces) in presence of water. The main component of biogas is methane.
Laboratory preparation
1. By coupling reaction of alkylhalide in
presence of sodium and dry ether. For
instance chlomethane couple with
chloromethane to form ethane
Na/dry ether
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2CH3Cl CH3CH3
2. By reduction of alkenes Example
CH3CH CH2 H2/NiCH3CH2CH3
propene propane
3. Reduction of alkynes Example
CH3C CH H2/PtCH3CH2CH3
Propyne propane
4. Reduction of alcohols Example
CH3CH2OH H2/NiCH3CH3
Ethanol ethane
5. Reduction of carbonyl compound
Example
CH3CHO H2/NiCH3CH3
Ethanal ethane
6. By reduction of carboxylic acid Example
CH3COOH H2/NiCH3CH3
Ethanoic acid ethane
7. By cracking long alkane
Cracking is the breakdown of long chain hydrocarbons into short alkanes.
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Cracking may be catalytic where a catalyst is used or thermal when heat is used.
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