CE ACAD

M.P.’s

SCIENCE ACADEMY
EN

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Chemistry
Aurangabad Class : XI

3] Topic : Alkenes (Hydrocarbon)

1] Introduction :
1. What are alkenes ?
Ans :
i] Alkenes are aliphatic unsaturated hydrcabrons containing one or more double bonds.
ii] Alkenes with one carbon-carbon double bond contain two hydrogen atoms less than corresponding
alkanes.
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iii]
iv] EN
The general molecular formula of aleken is C n H 2n .
The alkenes containing two double bonds are called as alka di enes.

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v] Alkenes containing three double bonds are call as alka trienes.

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vi] Alkenes are also called as olefins.

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vii] The simplest alkene is ethylene.

viii] Alkenes are more reactive than alkanes, due to the presence of CC

e.g. i] CH 2  CH 2 ii] CH 3  CH  CH 2
ethylene propylene
CH 3  C  CH 2
iii] | iv] CH 2  CH  CH  CH 2
CH 3
isobutylene Buta-1, 3-diene Or 1, 3-butadiene
Q.2. Why are alkenes called as olefins ?

Ans : Ethylene reacts with chlorine  Cl2  to form oily substance and therefore alkenes are called as olefins
(oil forming)
2] Uses of alkenes in our day to day life :
Alkenes play very important role in our daily life. The uses are as follows :
i] Ethylene (ethene) on polymerisation gives polyethene (polyethylene) which is a well known plastic.
Ethylene is also used for germination of seeds, flower maturation and ripening of fruits.
ii] Limonine (contain two double-bonds) is responsible for the smell of lemones and oranges.
iii]  -phellandrene is present in “Eucalyptus oil” structure of  -phellandrene :

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iv] Natural rubber is obtained from basic unit isoprene which contain two carbon carbon doubel bonds
structure of isoprene : CH 2  C  CH  CH 2
|
CH 3
IUPAC name of isoprene = 2-methyl buta-1, 3-diene.
v] Many edible oil contians fatty acids. They have one or more carbon-carbon double bonds.
e.g. C17 H 33COOH i.e. CH 3   CH 2   CH  CH   CH 2   COOH
7 7
oleic acid
vi] The orange pink colour of carrot is due to the presence of  -carotene (11 double bonds)
vii] The flavour of ginger is due to the presence of zingiberene (oil of ginger)
viii] The skin of apple contains a compound known as  -farnesene which contains four carbon-carbon
doubel bonds.
ix]
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Chemistry of vision of all animals is closely related to the chemistry of alkenes  -carotene decom-
C
poses to form vitamin-A which undergoes number of chemical reactions in presence of light which is
N
responsible for colour activating.
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3] Nomenclature in alkenes :
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Sr.No. Formula Common name IUPAC name

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1 CH 2  CH 2 ethylene ethene

2 CH 3  CH  CH 2 propylene prop-1-ene
or 1-propene
3 CH 3  CH 2  CH  CH 2  -butylene but-1-ene or 1-butene

4 CH 3  CH  CH  CH 3  -butylene but-2-ene or 2-butene

CH 3  C  CH 2
5 | iso-butylene 2-methylpropene or
CH 3
2-methyl prop-1-ene
6 CH 3  CH 2  CH 2  CH  CH 2  -pentylene pent-1-ene

7 CH 3  CH  CH  CH 2  CH 3  -pentylene pent-2-ene

CH3  CH  CH  CH 2
8 | iso-pentylene 3-methylbut-1-ene
CH 3

CH 3  CH  CH 2  CH  CH 2
9 | Iso-hexylene 4-methylhex-1-ene
CH3

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 CH3
|
CH 3  C  CH  CH 2
10 | Neo-hexylene 3,3-dimethylbut-1-ene
CH3

11 CH 3  CH  C  CH 2 Allene Buta-1,2-diene

4] Problems on nomenclature in alkenes :

Q.1. Writed the IUPAC name for following compounds.
CH 3  CH 2  C  CH 2
|
CH 2
1] |  2-ethylbut-1-ene
CH3
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2] | |
EN
CH 3  C  C  CH 2  CH 3
 2, 3-dimethyl pentene

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CH 3 CH3
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CH 2  C  CH  CH 3
| |

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3]  2, 3-Dimethyl but-1-ene
CH 3 CH 3

CH 2  CH  CH 2  CH  CH3
4] |  4-Methylpent-1-ene
CH 3

5] CH 3  CH 2  CH  CH  CH 2  CH 3  Hex-3-ene

CH 3
|
CH 3  C  CH  CH  CH 2  CH 3
6] |  2, 2-Dimethyl hex-3-ene
CH 3

CH3  CH  CH  CH 2
7] |  3-Methyl pent-1-ene
C2H5

CH3  CH  CH  CH 2
|
CH 2
i.e. |
CH 3

CH 3CH3
| |
CH 2  C  C  CH 3
8] |  2, 3, 3-trimethyl pent-1-ene
C2H5

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 CH 3 CH 3
| |
CH 2  C  C  CH 3
|
i.e. CH 2
|
CH 3

CH 2
9] ||  2-methyl but-1-ene
CH3  CH 2  C  CH 3

CH3  CH  CH 3
10] |  4-methyl pent-2-ene
CH  CH  CH 3

CH3
|
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11] |
CH 3 EN
CH 3  C  CH  C  CH 3
|
CH 3
 2, 4, 4-trimethyl pent-2-ene

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 CH3 2  C  CH  CH  CH2
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12]  4-methyl penta-1, 3-diene

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CH 3
i.e. |
CH 3  C  CH  CH  CH 2

13] CH 2  C  C  CH  CH 3  Penta-1, 2, 3-triene

CH 2  CH  CH  CH  C  CH 2
|
CH 2
14] |  2-Ethylhexa -1, 3, 5-triene
CH 3

CH 3  CH 2  CH 2  C   CH  CH 2  CH  C  CH  CH 3
15] | | |
CH 3 CH 3 CH 3
 2, 3, 7-trimethyl deca-3, 6-diene
CH 3  CH  CH  CH  CH 2
16] | |  3, 4-dimethyl pent-1-ene
CH 3 CH 3

CH 3  CH 2  C  CH 2  CH  CH 3
17] || |  2-Ethyl-4-methyl pent-1-ene
CH 2 CH 3

18]  CH3 2  C  CH  CH2  CH  CH3 2

CH 3  C  CH  CH 2  CH  CH 3
|  2, 5-dimethyl hex-2-ene
CH 3

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 CH 2  CH 3
|
19] CH 3  C  C  CH 3  3, 4-dimethyl hex-3-ene
|
CH 2
|
CH 3

20] H3 C  H 2 C  H 2 C  HC  H 2 C  HC  CH  CH  CH  CH 3
| | |
CH3 CH 2 CH3
|
CH 3
 3-ethyl 2, 7-dimethyldec-4-ene
Q.2. Write the structure for following compounds.
1] but-1-ene
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2] but-2-ene EN
CH 2  CH  CH 2  CH3 or CH 3  CH 2  CH  CH 2

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CH 3  CH  CH  CH3
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3] Pent-1-ene

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CH 3  CH 2  CH 2  CH  CH 2 or CH 2  CH  CH 2  CH 2  CH3
4] Pent-2-ene
CH 3  CH  CH  CH 2  CH 3
5] Buta-1, 3-diene
CH 2  CH  CH  CH 2
6] Penta-1, 3-diene
CH  CH  CH  CH  CH 3
7] Iso-pentylene
CH3  CH  CH  CH 2
|
CH 2
8] Isoprene or 2-methyl buta-1, 3-di ene
CH 2  C  CH  CH 2
|
CH3
9] Penta-1, 2, 3-triene
CH 2  C  C  CH  CH3
10] 2, 3-dimethylbuta-1, 3-diene

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 CH 2  C  C  CH 2
| |
CH 3 CH 3
11] 3-ethylpent-2-ene
CH 3  CH  C  CH 2  CH 3
|
CH 2
|
CH 2
12] 2-methylbuta-1, 3-diene
CH 2  C  CH  CH 2
|
CH3
13] 2, 3, 3-trimethyl but-1-ene
CH 3
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|
|
CH 2  C  C  CH 3
| EN

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CH 3 CH3
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14] 2, 5-dimethylhept-3-ene

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CH 3  CH  CH  CH  CH  CH 2  CH 3
| |
CH 2 CH 3
15] 3-ethyl-2-methylpent-2-ene
CH 3  C  C  CH 2  CH 3
| |
CH 3 CH 2
|
CH3
Q.3. Write the IUPAC name for following compounds (bond line representation)

1]  4-Methyl pent-1-ene

2]  2, 3-Dimethyl but-2-ene

3]  4-Ethyl-3, 5-Dimethyl hepta-2, 5

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4]  2, 4-Dimethyl hexa-2, 4-diene

5]  4-Methyl hepta-1, 3, 5-triene

6]  4-Ethyl-3, 5-Dimethyl hepta-1,6-diene

7] 
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Cyclobutene or Cyclobut-1-ene

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8]  Cyclohexene or Cyclohex-1-ene
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9]  4-ethyl hept-3-ene Y
Br

10]  4-Bromocyclopent-1-ene

Cl

Cl
11]  3, 4-dichlorocylohex-1-ene

12]  7-Ethyl-2, 4, 5, 6 tetra methyldeca 1, 8-diene

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5] Isomerism in alkenes :
Isomerism in Alkenes

Structural isomerism Geometrical isomerism

Chain Position Cis- Trans-

isomerism isomerism isomers isomers
Definition and Examples :
1] Chain isomerism :
The isomerism which is due the difference in the length of carbon chain called as chain isomerism i.e.

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difference in the structure of carbon chain.

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e.g.  -butylene and iso-butylene are the chain isomerism of each other..
CH 3  C  CH 2
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CH 3  CH 2  CH  CH 2 and
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CH 3
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 -butylene iso-butylene

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(but-1-ene) (2-methylprop-1-ene)
This molecular formula of  -butylene and iso-butylene is same i.e. C 4 H 8 .
2] Position isomerism :
The isomerism which is due to the difference in the position of double bond in the same carbon chain.
In position isomers molecular formula is same but difference in the position of double bond
e.g.  -Butylene and  -butylene
CH3  CH2  CH  CH 2 CH3  CH  CH  CH3
 but  1  ene   but  2  ene 
The molecular formula of  -butylene and  -butylene is same but difference in the position of double
bond.
3] Geometrical isomerism of cis-trans isomerism :
The isomerism which is due to the difference in spatial arrangement of groups or atoms around the
carbon-carbon double bond.
a] Cis-isomers :
The isomers in which two identical atoms or groups lie on the same side of the carbon-carbon double
bond are called as cis-isomers.
b] Trans-isomers :
The isomers in which two identical atoms or groups lie on the opposite side of the carbon-carbon
double bond are called as trans isomers.
Ex. i] Cis and Trans isomers of but-2-ene :
CH 3  CH  CH  CH3
but  2  ene

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 H H H CH 3
CC CC
CH3 CH 3 CH 3 H
cis but-2-ene Trans but-2-ene
Ex. ii] Cis and Trans isomers of pent-2-ene :
H H CH 3 H
CC CC
CH 3 C2H5 H C2 H 5
cis pent-2-ene
Point for entrance :
1] Trans isomers are mole stable than cis-isomers.

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2] Cis and Trans isomers have different phycial properties.
3]
4]
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The chemical properties of cis and trans isomers are similar, their reactivities may be different.
To show cis-trans isomerism each of the doubly bonded carbon atoms in alkenes must be attached
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to two different atoms or groups.

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5] Ethylene, propylene and alpha butylene do not show geometrical isomersm.

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6] Methods of preparation of alkenes :
1. Preparation of alkenes by dehydration alcohols by using concentrated or 75% H 2SO 4 .
i] Dehydration :
Dehydration means elemination of water molecule.
ii] Alcohols on dehydration gives alkenes.
iii] In this reaction -OH gets eleminated from  -carbon atom and -H gets eleminated from  -carbona
tom.
iv] This reaction is called as  -elemination reaction or 1, 2-elemination reaction.,
v] Dehydration of alcohol by using sulphuric acid known as acidic dehydration.
vi] The exact condition of dehydration depend upon the nature of alcohol.
Dehydration of primary alcohols :
1] Ethyl alcohol 10  when heated in presence of concentrated or 75% H 2SO 4 at about 413 K then
ethylene is obtained by dehydration.
conc. or 75% H 2SO 4
CH 3  CH 2  OH  413K
 CH 2  CH 2  H 2O
ethyl alcohol ethylene
2] n-butyl alcohol when heated in presence of concentrated or 75% H 2SO 4 at about 413 K then  -
butylene is obtained (main product)
conc. or 75% H2SO4
CH3  CH 2  CH 2  CH 2  OH  413K
 CH 3  CH 2  CH  CH 2  CH 2
n  butyl alcohol   butylene

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Dehydration of secondary alcohols :
1] Iso-propyl alcohol when heated in presence of 60% H 2SO 4 at about 373 K then propylene is
obtained by dehydration.
60% H 2SO 4
CH 3  CH  CH 3 373K
CH 3  CH  CH 2  H 2O
|
OH
iso  propyl alcohol propylene
(propan  2  ol)
Dehydration of tertiary alcohols :
1] Tertiary butyl alcohol when heated in presence of 20% H 2SO 4 at about 363 K then iso-butylene is
obtianed by dehydration.
CH 3
|

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20% H 2SO 4
CH 3  C  OH  363K
 CH3  C  CH 2  H 2O
|
CH 3
t  butyl alcohol NC |
CH 3
iso  butylene
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The ease of dehydration of alcohols in the order : 30  20  10 alcohol :
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A] Dehydration of secondary alcohol i.e. sec-butyl alcohol : Saytzeff rule or Zaitsev Rule :

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Sec-butyl alcohol (butan-2-ol) when heated in presence of 60% H 2SO 4 at about 373 K then a
mixture of but-1-ene (minor product and but-2-ene (major product) is obtained.
60%H 2SO 4
CH 3  CH  CH 2  CH 3 
373K
 CH 3  CH 2  CH  CH 2
| but  1  ene
OH  min or product 
sec  butyl alcohol 
 bu tan  2  ol  CH 3  CH  CH  CH 3
but  2  ene
 major product 

H2 O
In this reaction but-2-ene is the major product because dehydration takes place according to saytzeff
rule or Zaitsev rule.
Saytzeff rule or Zaitsev Rule :
When there are two possibilities for the elemination of hydrogen atom then ‘H’ gets eleminated from
that carbon atom which contain less no. of hydrogen atom and more stable alkene (having greater
no. of alkyl groups) is the main product.
2. Preparation of alkenes bydehalogneation of vicinal dihalides :
1. Dehalogenation :

Removal of two halogen atoms  X 2  from adjacent carbona tom is called as dehalogenation i.e.
elemination of Cl2 , Br2 , I 2 is called as dehalogneation.
2. Vicinal dihalides :
The dihalides in which two halogen atoms are attched to adjacent carbon atoms are called as vicinal
dihalides.

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 CH 2  CH 2 CH 2  Br
e.g. 1] | | or |
Br Br CH 2  Br
Common name - Ethylene dibromide IUPACA name 1, 2-dibromoethane
CH 3  CH  CH 2
2] | |
Cl Cl
propylene dichlroide, (1, 2-dichloroproane)
Preparation of alkenes by dehalogenation of vicinal dihalides :
Vicinal dihalides when heated with zinc metal +A presence of then alkenes are obtained by
dehalogneation
e.g. 1] Ethylene dibromide when heated with zinc meta then ethylene is obtained by dehalogenation.

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
CH 2  CH 2  Zn   CH 2  CH 2  ZnBr2
|
Br Br
|
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ethylene zinc
 ethene  bromide
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Q.1. How will you prepare propylene by dehalogenation of propylene dichloride Or what happen

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when 1, 2-dichloropropane heated with zinc.

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
CH 3  CH  CH 2  Zn   CH 3  CH  CH 2  ZnCl2

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| |
Cl Cl
Propylene dichloride propylene
(1, 2-dichloro propane)
3] Preparation of alkenes by dehydrahalogenation of alkyl halides :
i. When an alkyl halided boiled with alcoholic alklai such as alcoholic KOH or alcoholic NaOH then
alkenes are obtained by dehydrohalogenation.
ii. In this reaction halogen atom (-X) gets eliminated from  -carbon atom and hydrogen (H) gets
eliminated from  -carbon atom. Hence this reaction is called as dehydrohalogenation reaction.
iii] Dehydrohalogenation means removal of or elimination of hydrogen halide (-HX)
iv] As, H gets eleminated from  -carbon atom this reaction is called as  -elimination reaction.
v] The order of reactivity of alkyl halided towards dehydrohalogenation reaction is 30  20  10 alkyl
halides and ioiddes > bromides > chlorides.
e.g. 1] Dehydrohalogenation of ethyl bromide (10 alkyl halide)
Ethyl bromide when boiled with alcoholic KOH then ethylene is obtained by dehydrohalogenation.
 
boil
CH 3  CH 2  Br  KOH 
CH 2  CH 2  KBr  H 2 O
ethy alc. ethylene

e.g. 2] Dehydrohalogenation of isopropyl bromide  20 

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   
boil
CH 3  CH  CH3  KOH 

CH 3  CH  CH 2  KBr  H 2 O
|
Br
iso  propyl bromide propylene
(2  bromo propane)

e.g. 3] Dehydrohalogenation of t-butyl iodide  30  :

What is the action of alcoholic KOH and butyl iodide ?

CH 3
|
boil
CH 3  C  I  KOH  
CH 3  C  CH 2  KI  H 2 O
| alc |
CH 3 CH 3
t  butyl iodide
2  iodo  2  methyl
 CE ACAD
iso  butylene

Q.
propane

EN
What happens when iso-butyl bromideboiled with alc KOH ?

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boil
Ans : CH 3  CH  CH 2  Br  KOH  CH 3  C  CH 2  KBr  H 2 O
SC


| |

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CH3 CH3

iso-butyl bromide 10  iso-butylene

Dehydrohalogenation of sec-butyl bromide  20  that is Saytzeff rule or Zaitsev rule :

Sec-butyl bromide when boil with alcoholic KOH then a mixture of  -butylene (20%),    -
butylene (80%) is obtained by dehydrohalogenaiton in is reaction  -butylene is the major product
because dehydrhalogenation takes place according to Saytzeff rule and more stable alkenes (more
substituted) are the main product.
boil
CH 3  CH  CH 2  CH 3  KOH 
CH 3  CH 2  CH  CH 2
| alc.   butylene  but  1  ene 
Br 
sec butyl bromide CH 3  CH  CH  CH3
  butylene  but  2  ene 

KBr

H 2O
Point for Entrance :
1] The case of formation of alkene is in
R 2  C  C  R 2  R 2  C  CHR  R 2  C  CH 2  R  CH  CH  R  R  CH  CH 2
2] The order of stability of alkenes is as follow
R 2  C  CR 2  R 2  C  CHR  R 2  C  CH 2  R  CH  CH  R  R  CH  CH 2  CH 2  CH 2

M.P.’s Science Academy 12 Chemistry

4] Preparation of alkene form alkynes by partial reduction :
OR
Controlled hydrogenation of alkynes
i] The C  C bond of alkyens can be partially reduced to C=C with calcualted quantity of dihydrogen
 H2  in presence of Lindlar’s Catalyst.
ii] Lindlar’s catalyst is used for partial reducation :
iii] Lindlar’s catalyst is palladised charcoal deacativated partially with quinoline or sulpfur compound.
iv] Lindlar’s catalyst means
Pd- C (Quinaline or sulphur compound)
also Pd - CaCO3 and Lead acetate
v] By using catalyst cis-isomer obtained this

CE ACAD R R

N
Pd  Cl
R  C  C  R  H 2 
 CC
quinoline
Alkyne H
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Cis  alkene
H

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Example :
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1] Acetylene when react with hydrogen gas in presence of catalyst Pd-C and quinaline (lindlar’s cata-

Y
lyst) the ethylene is obtained.
Pd  Cquinoline
CH  CH  H 2 
Lindlar 'scatalyst
 CH 2  CH 2
Acetylene ethylene
2] Preperation of propylene from methyl acetylene by the action of Lindlar’s catalyst :
Pd  C and quinoline
CH 3  C  CH  H 2 
Lindlar 's catalyst
 CH 3  CH  CH 2
methyl Acetylene
Remeber, Alkynes when reduced in presence of sodium in liquid ammonia then trans alkenes are
obtained.
R H
Na in liquid NH3
R  C  C  R  H 2  CC
Alkyne H R
trans alkene
7] Physical properties of alkenes :
i] Ethylene, propylene and  -butylene are gases
ii] Except ethylene all other alkenes are odourless.
iii] Ethylene is a colourless gas with sweet odour.
iv] Next few memberans are liuqids and higher alkenes are solid.
v] Alkenes are less dense than water.
vi] Alkenes are insoluble in water but soluble in non-polar solvents like hexene, ether, chloroform.
vii] As the molecular mass increases boiling point of alkenes increases.

M.P.’s Science Academy 13 Chemistry

viii] Branched alkenes have lower boiling points then straight chain alkenes.
ix] The boiling point of alkene is very nearly same as that of alkene with the same carbon skeleton.

8] Chemical properties of alkenes :

1] Alkenes are more reactive than alkanes due to presence of  electrons.
2] Alekens undergo electrophilic addiiton reaction.
3] The different reactions of alkenes are as follows :
i] Formation of vicinal dihalides :
OR
Addition of Halogens to alkenes i.e. halogenation
1] Alkenes reacts with halogens and vicinal dihalides are formed.
2]
CE ACAD
The order of reactivity of halogen is Cl2  Br2  I2
3]
4]
EN
With iodine poor yield of di-iodide is obtianed.
In case of bromine, the red brown colourof bromine vanishes, as it is consumed by alkenes.

EM
5] This decolourization of bromine is used to detect the presence of C = C in the given compound.
I
SC

e.g. 1] Ethylene reacts with chlorine in presence of CCl 4 at room temperature, then ethylene dichloride

Y
is obtained.
CCl4
CH 2  CH 2  Cl2 
room temp.
 CH 2  CH 2
ethylene | |
Cl Cl
Ethylene dichloride
1, 2  dichloroethane 
CCl4
2] CH 3  CH  CH 2  Br2 
room temp.
 CH 3  CH  CH 2
propylene | |
Br Br
propylene dibromide
 2  dibromoprpoane 
1,
ii] Formation of alkyl halides :
OR
Addition of hydrogenhalide (H-X) :
i.e. Hydrohalogenaiton :
1] Alkenes reacts with hydrogen halides (H-X) and gives alkyl halides.
2] The order of reactivity of hydrogen halide is HI > HBr > HCl
3] i] Addiiton of HBr to symmetrical alkenes :
symmetrical alkenes reacts with hydrogen halides and gives only one product.
e.g. i] HBr when adds to ethylene then ethyl bromide is obtained
CH 2  CH 2  HBr  CH3  CH 2  Br
ethylene ethyl bromide
 symmetrical 
M.P.’s Science Academy 14 Chemistry
ii] HBr when adds to  -butyelen (symmetrical alkene) then sec-butyl bromide is obtained.

CH 3  CH  CH  CH 3  HBr  CH 3  CH  CH 2  CH 3
  butylene |
 symmetrical  Br
sec  butyl bromide
 2  bromobu tan e 
iii] Addition of HBr to unsymmetrical alkenes :
HBr (hydrogen halide) when adds to unsymmetrical alkenes two addition products become pos-
sible.
e.g. i] HBr when adds to propylene (unsymmetrical alkene) then two addition products become pos-
sible. One is n-propyl bromide and another is iso-propyl bromide

CH 3  CH 2  CH 2  Br

CE ACAD n  propyl bromide 

Minor product 
CH 3  CH  CH 2  HBr
EN

EM
I

CH 3  CH  CH3
SC

|
Br

Y
iso  propyl bromide 
Major product 
Experimentally it is observed that iso-propyl bromide is the major product because addition takes
place according to Markovnikov’s Rule.
Markovnikov’s Rule :
When an unsymmetrical reagent is added to an unsymmetrical alkene then the negative part of the
reagent attached to that carbon atom which carries the less no of hydrogen atoms.
Peroixde effect or Kharash Mayo effect OR Anti-Markovnikar’s rule OR Abnormal addition :
1] Perioxide effect is observed only in the case of HBr
2] The addition of HBr to an ansymmetrical alkeen depends upon the condition

e.g. HBr when adds to propylene in presence peroixde such as hydrogen peroixde  H 2O 2  or sodium
 C 6 H5  C  O  O  C  C6 H 5 
peroxide  Na 2O 2  or benzoyl peroxide  || || 

 O O 
n-propyl bromide is obtained i.e. Anti-Markovnikov’s addiiton takes place. This is known as peroixide
effect OR Kharash Mayo effect OR abnormal addition.
in presence
CH 3  CH  CH 2  HBr 
of peroxide
 CH 3  CH 2  CH 2  Br
propylene n  propyl bromide
 unsymmetrical 
HBr when adds to propylene in the absence of peroixide then addition takes place according to
Markovnikov’s rule and iso-propyl bromide is obtained.

M.P.’s Science Academy 15 Chemistry

 in absence
CH 3  CH  CH 2  HBr 
of peroxide
 CH 3  CH  CH 3
propylene |
 unsymmetrical  Br
Point for Entrance :
1. Peroxide effect is not absent in case of HCl and HI.
iii] Formation of Alkyl hydrogen sulphate and alcohols i.e. Addition of sulphuric acid
 H  OSO3H  : -
Alkenes reacts with concentrted sulphuric acid and gives alkyl hydrogen sulphate which on boiling
with water gives corresponding alcohols. This process is called as ‘Hydration of alkenes’
e.g. 1] Preparation of ethyl alcohol from ethylene :
|Ethylene reacts with concentrated sulphuric acid and gives ethyl hydrogen sulphate. Which on boil-
ing with water gives ethyl alcohol.

CE ACAD
CH 2  CH 2  H  OSO3H  CH 3  CH 2  OSO3H
Step 1 : ethylene conc.

EN
ethyl hydrogen
sulphate

EM
boil
CH 3  CH 2  OSO3H  H  OH  CH 3  CH 2  OH  H 2SO 4
I


water ethyl alcohol
SC

Step 2 :
 ethanol 

Y
2] Preparation of iso-propyl alcohol from propylen
M.K.rule
CH 3  CH  CH 2  H  OSO3   CH 3  CH  CH3
propylene |
Step 1 :
 unsymmetrical  OSO3 H
iso  propyl
hydrogen sulphate
boil
CH 3  CH  CH 3  H  OH 

CH 3  CH  CH3  H 2SO 4
| |
Step 2 : OSO3 H OH
iso  propyl alcohol
Reactive alkenes like iso-butylene reacts with water molecules in presence of concentrated sulphuric
acid gives t-butyl alcohol means addition of water to unsymmetrical alkenes takes place according to
Markovnikov’s rule i.e. M. K. rule.
CH 3
|
conc.H 2SO 4
CH 3  C  CH 2  H  OH 
M.K.rule
 CH 3  C  OH
| |
CH 3 CH 3
iso  butylene iso  butyl alcohol
iv] Formationof Glycols OR hydroxylation :
i.e. Baeyer’s test.
1] Glycols :

Glycols are dihydric alcohols in which to hydroxyl groups  OH  are attached to adjacnet carbon
atoms.
M.P.’s Science Academy 16 Chemistry
 They are also called as vicinal glycols
OR 1, 2-diol
CH 2  CH 2 CH 2  OH
e.g. 1] | | OR |
OH OH CH 2  OH
ethylene glycol
(ethane-1, 2-diol)
CH 3  CH  CH 2
| |
OH OH
propylene glycol (propane (-1, 2-diol)
2.
E ACAD
Alkenes reacts with cold and dilute KMnO 4 solution and gives glcyols.
C
3.

4. EN
Bayer’s reagent means cold and dilute KMnO 4 solution.

In this reaction the purple colour (violet colour) of KMnO 4 disappears.

EM
I

5. It is the laboratory test to identify the presence of double bond. This test is known as Baeyer’s test.
SC

1. Ethylene when reacts with cold and dil. KMnO 4 solution (Baeyer’s reagent) then ethylene glycol is

Y
obtained.
cold and KMnO4
CH 2  CH 2  H 2O   O  
Baeyer 's reagent
CH 2  CH 2
ethylene | |
OH OH
ethylene glycol
 ethane  1, 2  diol 
Q. How will you convert propylene to proylene glycol.
cold and dil. KMnO 4
CH 3  CH  CH 2  H 2O  O  
Baeyer 's reagent
 CH 3  CH  CH 2
Propylene | |
OH OH
Ans : propylene glycol
 propane-1, 2-diol 
v] Formation of aldehydes or Ketones Or both Or ozonolysis of alkenes i.e. Addiiton of ozone
to alkene :
1. When ozone or ozonied oxygen passed through an alkene in presence of solvent CCl 4 then ozo-
nides are formed which are unstable.
2. Ozonides on reduction with zinc dust and water gives either aldehydes or ketones or both.
e.g. 1] Ozonolysis of ethylene :
When ozone pass through ethylene in presence of CCl4 then ethylene ozonide is formed which on
reduction with zinc dust and water gives formaldehyde.

M.P.’s Science Academy 17 Chemistry

 CCl4
CH 2  CH 2  O3   CH 2  O  CH 2
ethylene
Step 1] O O
ethylene ozonide

H2 O
CH 2  O  CH 2  Zn   2H 2O  ZnO
or
Step 2 : O O H  CHO
formaldehyde

2] Ozonolysis of propylene i.e. addition of O3 to propylene :

CCl4
CH 2  CH  CH 2  O3   CH3  CH  O  CH 2

Step : 1] propylene O O
propylene ozonide

CE ACAD
H2 O

Step : 2]
O O
EN
CH 3  CH  O  CH 2  Zn   CH 3  CHO  H  CHO  ZnO

EM
I

i] The reaction of alkene with ozone to give ozonide followed by hydrolysis is called as ozonolysis.
SC

ii] The ring is reptured (breaking) at the position of double bond.

Y
iii] Ozonolysis reaction is used
a] To detect the position of double bonds in alkenes.
b] To find out the no. of double bonds in alkenes.
Q.1. Give the reaction for the ozonolysis of  - butylene or But-1-ene.
CCl4
CH 3  CH 2  CH  CH 2  O3   CH 3  CH 2  CH  O  CH 2
  butylene
O O
Zn  H 2O
CH 3  CH 2  CHO  H  CHO  ZnO

Q.2. Give the ozonolysis reaction of  -butylene or but-2-ene.

CCl4
CH 3  CH  CH  CH3   CH 3  CH  O  CH  CH3

O O
  butylene ozonoide
Zn  H 2 O
2CH 3  CHO  ZnO
acetaldehyde
Q.3. Give the ozonolysis reaction of 2, 3-dimethyl but-2-ene.

M.P.’s Science Academy 18 Chemistry

 CCl4
CH 3  C  C  CH3  O3   CH 3  C  O  C  CH 3
| |
CH 3CH3 CH 3 O O CH 3

Zn H 2O
 CH 3  C  O 
2 |   ZnO
 CH 
 3 
acetone 2  methylketone 

vi] Oxidation of alkenes :

1. Alkenes on oxidation give ketones nd carboxylic acids depending upon thenature of alkene and
experimental condition.

2. Oxidation of alkene is carried out in preesnce of acidic potassium permagnate  KMnO 4 / H   or

 K Cr O
2 2 7
CE ACAD
/ H   acidic potassium dichromate.

N
e.g. 1] Propylene when oxidised in presence of acidic potassium permagnate then acetic acid id obtianed
E

EM

 
KMnO4 / H
I

CH 3  CH  CH 2  4 O 
oxidation
CH3  COOH  CO 2  H 2O
SC

propylene

Y
2]  - butylene when oxidised in presence of acid potassium permagnate then acetic aicd is obtained.
KMnO4
CH3  CH  CH  CH3  4  O 
oxidation
 2 CH3  COOH
  butylene
3] 2-methylbut-2-ene on oxidation in presence of acidic KMnO 4 gives acetone and acidic acid.

CH 3  C  CH  CH 3  3 O  
KMnO 4 / H
oxidation
CH 3  C  CH 3
| ||
CH 3 O
2  methyl but  2  ene  CH 3  COOH
vii] Polymerisation of alkenes :
1. A process in which large no. of small molecules (monomers) combine together to form a long chain
molecule (polymer) is called as polymerisaiton.
2. A polymer is a macromolecule. A polymer containing rep known as monomer.
3. Polymer have very high molecular weight. During polymerisation no. of monomers are joined to-
gether by covalent bond.
e.g.1] Ethylene on heating under atmospheric pressure and presence of oxygen gives a long chain polymer
known as polyethene polyetheylene
Heat
n CH 2  CH 2 
und atm pressure of O 2
  CH 2  CH 2 
ethylene / ethene polyethye ln e / polyethe
 Monomer 
Polyethene contains thousnad units of ethene
Polyethene is chemically inert, tough, water proof and poor conductor of electricity.

M.P.’s Science Academy 19 Chemistry

 Name of monomer Name of the polymer
1. CH 2  CHCl Poly vinyl chloride
vinyl chloride

CH 2  C  CH  CH 2
2. | Natural rubber
CH 3
iso-proene
2-methylbuta-1, 3-diene

3. CF2  CF2 Teflon/

Tetrafluro ethylene or
tetra fluoro ethene CE ACAD
Polytetra fluroethene (PTFE)

CH  CH 2
EN

EM
I
SC

4. Polystyrene

Y
styrene
8] Hydroboration - oxidation reaction of alkenes :
1. In hydroboration oxidation reaction alkenes reacts with diborone in prenece of solvent THF (tet-
rahydrofuran) and gives tri-alkyl borane.
2. Tri-alkyl borane on oxidation by using hydrogen peroxide in presence of aqeous NaOH (alkaline
medium) gives primary alcohols  R  CH 2  OH 
3. The overall reaction gives anti Markovnikov’s products from unsymmetrical alkenes.
e.g.1] Preparation of ethyl alcohol from ethylene by hydroboration oxidation reaction :
Ethylene reacts with diborane in presence of solvent THF and gives tri-ethyl borane, tri-ethyl borane
reacts with H 2 O 2 in presence of aqueous NaOH and yields ethyl alcohol.
THF
Step i] 6CH 2  CH 2  B2 H 6   2  CH3  CH 2 3 B
tri-ethylborane
aq.NaOH
Step ii] 2  CH3  CH 2 3 B  3H 2 O 2 
alkaline medium
 CH3  CH 2  OH  H3BO3
ethyl Boric

alcohol 10  acid

M.P.’s Science Academy 20 Chemistry

2] Preparation of n-propyl alcohol from propylene by hydrboration oxidation reaction.
THF
Step I : 6CH 3  CH  CH 2  B2 H 6   2  CH3  CH 2  CH 2 3 B
propylene diborane tri-n-propyl borane
aq.NaOH
Step II :  CH3  CH 2  CH 2 3 B  3H 2 O 2 
alkaline
 3CH 3  CH 2  CH 2  OH  H 3O
medium

n-propylalcohol 10 
9] Uses of Alekens :
1. Ethylene is used for artificial ripening of fruits such as mango.
2. Ethylene and propylene also used to manufacture polyethene and polypropylene which are used to
prepare pipes, bottles, toys, bags, etc.
3. Alkenes are used as starting materials in the preparation of several compounds like alkyl halides,

4. CE ACAD
aldehydes, ketones, acids, alcohols glycols etc.
In combination with oxygen ethylene used as oxyethylene flame, which is used for cutting and weld-
ing of metals.
EN

EM
I

*****
SC

M.P.’s Science Academy 21 Chemistry