Alkenes 2

CHAPTER 13
Hydrocarbons
Alkenes
Part 2
Prepared by: Cik Suhaila
For F5
1
Chemical Reaction Of Alkenes

Alkenes are more reactive compared to alkanes
Comparison between alkanes and alkenes

Alkanes
less reactive
Alkenes
more reactive
has C-C single

has C-C double
bond
bond
( bond) : more
( bond) : less
stable
undergoes free radicalstable
undergoes electrop
substitution reaction
2
addition reaction
Why alkenes are more reactive

3 Reasons
1 C-C double bond in alkenes consist of one and
one bond
bond is weaker than bond.
bond is easier to break, while bond
(in alkane) remains intact
2 bond in the double bond act as a source of
electrons.
alkenes is reactive towards electrophile
3
3 When bond is broken : provide side for new

covalent bond to form. One bond can form 2
bonds.
Breaking of bond is more favourable than
breaking of bond (because less energy
is needed for breaking bond)
Addition Rxn
Reaction in which an unsaturated system becomes
saturated by addition of molecules across the
multiple bond
Has 3 characteristics :
Breaking of bond, forming 2 bonds
Only one product is obtained at the end of rxn
The product is saturated organic compound
Electrophilic Reaction Mechanis

Of Alkenes
The mechanism take place in 2 steps
STEP 1 Formation of a carbocation
The rxn begins with an attack by the electrophile
(E+) on the electrons of the double bond which
acts as the nucleophile
C
+ + EY
slow
C
+
E
carbocation
+ :Y6
STEP 2 Rapid rxn with negative ion

The negative ion ( :Y- ) acts as the nucleophile and
attacks the positively charge carbon atom to give
the product of addition rxn.
C
E
C
+
carbocation
+ :Y-
fast
product
Reaction of
Alkenes
Hydrogenation of
alkenes
Halogenation of
alkenes
In inert solvent,
CCl4
In aqueous
solution
Hydrohalogenation of
alkenes
Addition of HBr in the presence
of peroxides
8
Continue
Hydration of alkenes
Oxidation of alkenes
Reaction of
Alkenes
With cold and dilute

KMnO4
With hot and conc.
KMnO4
Addition of sulphuric
acid
Ozonolys
is
Hydrogenation Of
Alkenes
Hydrogenation means addition of H atom to
multiple bonds to form saturated product
Alkene reacts with H2 (g) to form alkane, in the

presence of metal catalyst (Pt/Pd/Ni)
General rxn :
Alkene
+ H2
Pt/Pd/Ni
Alkane
10
Example,
CH3-C=CH2 + H2
Pt/Pd/Ni
H
propene
CH3-CH2-CH3
propane
Example,
+ H2
cyclohexene
Pt/Pd/Ni
cyclohexane
11
Hydrogenation of alkene
Important process in food indus

Use to harden unsaturated fats
oils to make margarine
Presence of C = C in the oils low

the melting point makes them
too soft for commercial use
Therefore, they are hydrogenat
to produce margarine
12
Halogenation Of
Alkenes
(a) In inert
solvent, CCl4
in CCl4 at
room temperature, to form vicinal dihalides
Alkene reacts with chlorine and bromine
Vicinal DiHalide
2 substituents (in this case halogens)
are attached to the adjacent C atoms
13
General rxn :
C
+ X2
CCl4
Alkene
CH3 H
2-methyl-2-butene
Vicinal dihalide
Example,
CH3-C = C-CH3 + Cl
2
Cl
CCl4
Cl
CH3-C - C-CH3
CH3 H
2,3-dichloro-2-methylbutane
14
Bromine test
of any alkene with bromine
ReactionHalogenation
:
water in presence of CCl4
Useful As
: a test for unsaturation (the presence
of double bond or triple bond)
ObservationWhen
: unsaturated compound presence
The colour of bromine changes from
reddish-brown colour to colourless
When saturated compound presence
The colour of bromine remain unchange
15
Bromine test
A
PLACE A SOLUTION OF
BROMINE IN A TEST TUBE
ADD THE HYDROCARBON

TO BE TESTED AND SHAKE
IF THE BROWN COLOUR

DISAPPEARS THEN THE
HYDROCARBON IS AN
ALKENE
colourless
+ Br2
reddish
brown
CCl4
Br Br
colourless
16
Bromine test
This test is used to distinguish alkenes fr

CH3-CH
CH2 + Br2
propene
CCl4
dark
CH3-CH-CH2
Br Br
1,2-dibromopropane
Observation : The colour change from reddish-brown

to colourless
CH3-CH2-CH3
propane
+ Br2
CCl4
dark
No Reaction
Observation : The colour of bromine remain unchange

17
Halogenation Of
Alkenes
(b) In aqueous
solution
Halogenation of alkene in aqueous solution,
formed haloalcohol (halohydrin)

General rxn :
Alkene
+ X2
H 2O
OH-
OH
halohydrin
18
Example,
H
H
H
H
+ Br2
H2O
Br OH
ethene
bromoethanol
NOTE !
If the alkenes is unsymmetrical, the halogen ends up

on the carbon atom with the greater number of
hydrogen atoms.
19
Example,
OHCH3
CH2
CH3
+ Br2
2-methyl-1-propane
OH Br
H2O
CH3
CH2
CH3
1-bromo-2-methyl-2-propanol
Example,
CH3
+ Cl2
1-methylcyclohexene
H2O
OH
Cl H
CH3
20
2-chloro-1-methyl-1-cyclohexenol
Hydrohalogenation Of
Alkenes
Alkenes react with hydrogen halides (HX) to form
haloalkanes
Hydrogen and halogen atoms are added across the
double bond
General rxn :
Alkene
+ HX
X H
haloalkanes
21
Example,
H and halogen atoms can be added to the
C = C in 2 different ways :
MAJOR
PRODUCT
CH3
3
CH3
Br H
2-bromopropane
H + HBr
propene
MINOR
PRODUCT
CH3
H Br
1-bromopropane
22
How to predict the

MAJOR and MINOR PRODUCT ?
t Can Be Explain In Term Of

MARKOVNIKOVs RULE
23
Markovnikovs Rule
addition of HX, the more electropositi

reagent (usually H atom) is added to
e double bond Carbon which has great
number of Hydrogen atoms
24
Example, Propene
MAJOR
PRODUCT
CH3
+ H + HBr
MINOR
PRODUCT
CH3
Br H
2-bromopropane
CH3
H Br
1-bromopropane
25
Example, 2-methylpropene
CH3
CH3
CH2
2-methylpropene
+ + HCl
CH3
CH3
CH2
Cl H
2-chloro-2-methylpropene
MAJOR PRODUCT
CH3
CH3
CH2
H Cl
1-chloro-2-methylpropene
MINOR PRODUCT
26
4 Addition Of HBr In The

Presence
Of
Peroxides
When alkene reacts with HBr in the presence of

peroxide (e.g. H2O2), addition occurs in an
Anti-Markovnikov manner
Whereby that the hydrogen atom of HBr attach to
the double bond carbon with fewer hydrogen atoms.
C
Alkene
+ HBr
ROOR
Br H
haloalkanes
27
Example,
CH3
propene
+ H + HBr
H2O2
CH3
H Br
1-bromopropane
MAJOR PRODUCT
28
Hydration Of
Alkenes
Hydration is addition of water
Addition of water to the C=C of alkene follows the
Markovnikovs rule and alcohol is formed.
The rxn is catalysed by strong acids, which protonate
water molecules, to give the electrophile, H 3O+
Alkene
+ H2O Diluted
acid
OH H
alcohol
29
Example,
H+
CH3
CH3
CH2
+ H2O
OH2-methylpropene
CH3
H+ @
H3O+
CH3
CH2
OH H
2-methyl-2-propenol
MAJOR PRODUCT
CH3
CH3
CH2
H OH
2-methyl-1-propenol
30
MINOR PRODUCT
Oxidation Of
Alkenes
(a) With cold and diluted

KMnO4
Pottasium permanganete, KMnO4 in basic can be

used to oxidised elkene to
1,2-diol (glycol)
Two OH groups are added to the C-C double bond
Alkene
OH
+ KMnO4
(purple) cold
OH OH
gylcol
+ MnO2
(brown)
31
This rxn is also known as Beayers Test

It can be used to test the presence the C-C double
bond in the compound
Observation :
The purple colour of the KMnO4 decolourised,
and brown precipitate of MnO2 is formed
Example,
CH2
CH2 + KMnO4
ethene
H2O, OHcold
CH2
CH2
OH
OH
+ MnO2
ethane-1,2-diol
32
Oxidation Of
Alkenes
(b) With hot and

concentrated KMnO4
When oxidation of alkene is carried out in
hot, concentrated and acidic KMnO4 ,

it involved the cleavage of C-C double bond
The products are containing

C
Alkene
+
conc
/
H
+ KMnO4
hot
C = O group
C=O + O=C
2 carbonyl compound
33
Example,
CH3
CH3
CH3
CH3 + KMnO4
CH3
2,3-dimethyl-2-butene
conc / H+
hot
CH3
+
O
CH3
CH3
propanone
(ketone)
34
Notes !
If the double bond is
2 carbonyl produc
tetrasubstituted
(ketones) are obtaine
If 1 H present on
carboxylic acid
the double bond
is obtained
If 2 Hs present on
CO2 and H2O
1C
is obtained
35
Example,
1 H on the
C double bond
CH2
CH-CH3
propene
2 H on the
C double bond
+ KMnO4
conc / H+
hot
O
OH-C-CH3
ethanoic acid
(carboxylic acid)
+ CO2
+ H2O
36
The Rxn is used to establish the location of

the double bond
Example
An alkene with the molecular formula C 6H12 is
oxidised with hot KMnO4 solution. The carboxylic
acid, butanoic acid (CH3CH2CH2COOH) and
ethanoic acid (CH3COOH) are produced. Identify
Solution
the structural formula of the alkene.
Product -
1) Butanoic acid (CH3CH2CH2COOH)

2) Ethanoic acid (CH3COOH)
37
Solution - continue
- 2 oxygen
CH3-CH2-CH2-C OO H
CH3-CH2-CH2-CH -
Butanoic acid
CH3-C OO H
Ethanoic acid
CH3-CH - 2 oxygen
CH3-CH2-CH2-CH = CH-CH3
Alkene used in the rxn is :
2-hexene
38
7 Addition Of Sulphuric Acid To

Alkenes
Alkenes dissolve in concentrated H2SO4 :
to form alkyl hydrogen sulphates

Alkyl hydrogen sulphates is then hydrolysed (by
heating with water :
to form alcohol
The rxn follow Markovnikovs rule
39
General Rxn
C
Alkene
H2SO4
(conc)
Hydrolysis
C
OSO3H
H-OH
Alkyl hydrogen
sulphate
H2SO4 +
OH
Alcohol
40
H
C
H H
+
CH3
propene
H2SO4
(conc)
Hydrolysis
CH3
OSO3H
H-OH
Alkyl hydrogen
sulphate
H H
H
OH
CH3
propanol
41
Ozonolysis Of
Alkenes
More widely used method for
bond
locating the doub
of an alkene involves the use of ozone (O 3)
Ozone reacts vigorously with alkenes to form

unstable compounds called
molozonides.
Molozonides then rearrange spontaneously to

form
ozonides.
Ozonides involves the cleavage of the C-C double

bond, in presence of
Zn/H+ and H2O.
The products is the carbonyl compounds (aldehydes

or ketones
42
General Rxn
H
R
R
Alkene
O3
H
R
O
C
R
R
Ozonide
(i) Zn/H+
(ii) H2O
HC=O
R
O=CR
R
43
Example
CH3
CH3
O3
CH3
CH3
CH3
2-methyl-2-butene
O
C
H
CH3
Ozonide
(i) Zn/H+
(ii) H2O
CH3 C = O
CH3
propanone
O=CH
CH3
ethanal
44
END
OF ALKENES
45

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CHAPTER 13

Chemical Reaction Of Alkenes

Comparison between alkanes and alkenes

has C-C single

Why alkenes are more reactive

3 When bond is broken : provide side for new

Electrophilic Reaction Mechanis

STEP 2 Rapid rxn with negative ion

With cold and dilute

Alkene reacts with H2 (g) to form alkane, in the

Important process in food indus

Presence of C = C in the oils low

Alkene reacts with chlorine and bromine

ADD THE HYDROCARBON

IF THE BROWN COLOUR

This test is used to distinguish alkenes fr

Observation : The colour change from reddish-brown

Observation : The colour of bromine remain unchange

Halogenation of alkene in aqueous solution,

formed haloalcohol (halohydrin)

If the alkenes is unsymmetrical, the halogen ends up

Alkenes react with hydrogen halides (HX) to form

How to predict the

t Can Be Explain In Term Of

addition of HX, the more electropositi

4 Addition Of HBr In The

When alkene reacts with HBr in the presence of

(a) With cold and diluted

Pottasium permanganete, KMnO4 in basic can be

Two OH groups are added to the C-C double bond

This rxn is also known as Beayers Test

(b) With hot and

When oxidation of alkene is carried out in

hot, concentrated and acidic KMnO4 ,

The products are containing

(ketones) are obtaine

the double bond

CO2 and H2O

The Rxn is used to establish the location of

1) Butanoic acid (CH3CH2CH2COOH)

7 Addition Of Sulphuric Acid To

Alkenes dissolve in concentrated H2SO4 :

to form alkyl hydrogen sulphates

The rxn follow Markovnikovs rule

More widely used method for

locating the doub

of an alkene involves the use of ozone (O 3)

Ozone reacts vigorously with alkenes to form

Molozonides then rearrange spontaneously to

Ozonides involves the cleavage of the C-C double

Zn/H+ and H2O.

The products is the carbonyl compounds (aldehydes

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