Alkenes

The alkenes are unsaturated hydrocarbon containing at least

one carbon to carbon double bond in their molecules. These
are also known as olefins. They have general formula CnH2n.
Where n= 1,2,3……..
Example CH2 = CH2, CH3- CH = CH2, CH3- CH= CH-CH3
Ethene Propene 2-Butene
General methods of preparation:
1. From dehydration of alcohol:
When alcohol is heated with dehydrating agent like conc.
H2SO4, P2O5 , Alumina, etc.; alkene is formed.
RCH2CH2OH H2SO4/170°C RCH=CH2 + H2O
alkene
Example CH3CH2OH H2SO4/170°C CH2=CH2 + H2O
2. By dehydrohalogenation:
When an alkyl halide is heated with an alcoholic solution of
KOH or NaOH alkene is formed .
RCH2CH2X + KOH (alc.) RCH2=CH2 +KX + H2O
Example, CH3CH2Cl + KOH CH2=CH2+KCl + H2O
3. From catalytic hydrogenation of alkynes :
When alkynes are heated with hydrogen gas in the presence of
catalyst (Lindlar’s catalyst : Pd/BaSO4 ), They are converted to
corresponding alkenes.
Pd/BaSO4
RC≡CH + H2 RCH2=CH2
Example CH≡CH + H2 Pd/BaSO4 CH2=CH2
4. From Kolbe’s electrolysis :
Alkenes can be prepared by the electrolysis of aqueous
solution of sodium or potassium salt of dicarboxylic acid.
Example, When potassium succinate is electrolyzed between
platinum electrodes, ethene is produced at anode.
CH2COOK CH2COO-
│ │ + 2K+
CH2COOK CH2COO-
At anode
CH2COO - CH2COO
│ │ + 2e-
CH2COO - CH2COO
CH2COO -CO CH2
2
│ ││

CH2COO CH2
At cathode
2K+ + 2e- 2K
2K + 2H O 2KOH + H
 Laboratory preparation of ethene (or Ethylene):
Principle:
Ethene is prepared in laboratory by heating ethanol with conc.
H2SO4 at 170°C. Conc. H2SO4 act as dehydrating agent.
Reaction complete in two step.
100°C
CH3CH2OH + H2SO4 CH3CH2HSO4 + H2O
170°C
CH3CH2HSO4 CH2=CH2+ H2SO4
Experimental setup:
Fig. : Laboratory preparation of ethene.
Procedure:
A mixture of ethyl alcohol and conc. H2SO4 in the ratio 1:2 is
taken in round bottom flask; fitted with dropping funnel,
thermometer and delivery tube. Small amount of sand and
aluminium sulphate is added to the flask to prevent frothing.
The flask is heated in sand bath at 170°C. The ethene gas is
evolved.
The gas thus produced may contain SO2 and CO2 as a
impurities then the gas is passed through a aqueous solution of
NaOH where the impurities are absorbed. Finally pure ethene
gas is collected in gas jar by downward displacement of water.
SO2 + NaOH Na2SO3 + H2O
CO2 + NaOH Na2CO3 + H2O
 Physical properties:
1. The first three member are gases, while alkenes having 5 to
15 carbon are liquid and higher alkenes are solid at room
temperature.
2. They are insoluble in water and soluble in organic solvent.
3. The density of alkenes is less than water.
Chemical properties:
1. Addition reaction:
Alkenes undergo addition reaction with various reagents to
give the saturated compound . In addition reaction ᴨ- bond
is converted in to new σ- bond in product.
i) Addition of hydrogen (catalytic hydrogenation):
Alkenes when heated with hydrogen gas in the presence of
catalyst like Ni, Pt, Pd etc. at high temp. to give alkanes.
 Ni/∆
R- CH = CH2 + H2 R- CH2- CH3
Ni/∆
Example, CH2 =CH2 + H2 CH3- CH3
ii) Addition of halogen (Halogenations):
Alkene react with halogen to give dihaloalkane.
R-CH=CH2 + X2 R-CH-CH2
│ │
X X
Example, CH2=CH2 + Cl2 CH2ClCH2Cl
iii) Addition of water (Hydration):
In the presence of phosphoric acid (H3PO4) at high
temperature and pressure, Alkene react with water to form
alcohol.
H+/70atm,300°C
R-CH=CH2 + H2O RCH-CH3
OH
 H+/70atm,300°C
Example, CH2=CH2 + H2O CH3CH2OH
iv)Addition of sulphuric acid:
Alkene react with cold and conc. Sulphuric acid to give ethyl
hydrogen sulphate. The product when boiled with water gives
alcohol. H2 O
RCH=CH2 + H2SO4 RCH-CH3 RCH-CH3 + H2SO4
│ │
OSO3H OH
Example
CH2=CH2 + H2SO4 CH3CH2OSO3H H2O CH3CH2OH +
H2SO4
v)Addition of halogen acid:
Alkene react with halogen acid to give alkyl halide.
RCH=CH2 + HX RCH2CHX
Example, CH2=CH2 + HBr CH3CH2Br
Markovnikov’s rule:
The addition of halo acid or other unsymmetrical reagent(like
HCl, HBr, H2O, HI etc.) to unsymmetrical alkene in a such
way that the positive part of the reagent goes to that double
bonded carbon atom having greater number of hydrogen atom
and negative part of reagent goes to that double bonded carbon
atom having lesser number of hydrogen atom.
CH3-CH2-CH=CH2 + HBr CH3-CH2-CH-CH3
│
Br
Peroxide effect (or Anti Markovnikov’s rule or Kharash
effect):
in the presence of organic peroxide(R-O-O-R) the addition of
of halo acid or other unsymmetrical reagent(like HCl, HBr,
H2O, HI etc.) to unsymmetrical alkene in a such way that the
positive part of the reagent goes to that double bonded carbon
atom having lesser number of hydrogen atom and negative
part of reagent goes to that double bonded carbon atom having
greater number of hydrogen atom.
CH3-CH2-CH=CH2 + HBr Organic peroxide CH3-CH2-CH2-CH2
│
Br
vi)Addition of ozone (Ozonolysis) :
Alkenes react with ozone in inert solvent gives unstable
product called ozonide, which on heating with zinc in water
forms corresponding carbonyl compound. The reaction is
called ozonolysis.
 O Zn/H2O;∆
>C=C< + O3 >C C< >C=O + >C=O
O–O O
Zn/H2O;∆
Example , CH2=CH2 + O3 H2C CH2
2HCH + H2O2 O–O
ǁ
O
Formaldehyde
2. Oxidation with alkaline KMnO4(Baeyer’s test):
Alkenes are readlly oxidized by alkaline KMnO4(Baeyer’s
reagent : 1% alkaline KMnO4 solution ) to glycol. During this
reaction pink colour of KMnO4 is discharged. This reaction is
commonly known as Baeyer’s test for unsaturation.
KMnO4 + 2KOH 2KMnO4 + H2O + [O]
>C=C< + H2O + [O] >C – C<
│ │
OH OH
Example, CH2=CH2 + H2O + [O] CH2 – CH2
│ │
OH OH
Ethylene glycol
3.Oxidation with acidic KMnO4
Acidic KMnO4 oxidize alkene into carboxylic acid.
KMnO4 + H2SO4 K2SO4 + MnSO4 + H2O + [O]
CH2=CH2 + 4[O] 2HCOOH
4. Polymerization:
The process in which the large number of simple molecule
combine to form high molecular weight compound (Polymer)
is called polymerization. These simple molecules having low
molecular mass are known as monomers.
By the polymerization process large number of synthetic
polymer are prepared. The polymers are used in plastic,
rubber and many other industry.
Monomer Polymerization polymer
When ethene molecule undergoes polymerization at high
pressure and temperature then polythene is formed.
nCH2=CH2 Polymerization (-CH2-CH2-)n
Ethene polyethene
Test for alkenes
1. Bayer’s test:
2. Bromine test:
A solution of bromine in carbon tetrachloride or bromine in
Water is added to given organic compound then the brown
colour of bromine solution is discharged indicates the
presence of double bond.
CCl4
Example, CH2=CH2 + Br2 CH2 – CH2
│ │
Br Br
1, 2 – dibromoethane(colourless)
Uses:
1. Ethene is used for manufacture of plastic, rain coats pipe
etc.
2.It is used for oxy-ethylene flame for cutting and welding of
metals.
3. It is used for artificial ripening of fruits.