ASC0303

ORGANIC CHEMISTRY

CHAPTER 3
ALKENES AND CYCLOALKENES

PUSAT ASASI SAINS

 C
H
Learning outcomes A
P
Nomenclature of Alkenes T
State the general Formula for alkenes and cycloalkenes E
Name and draw the alkenes according to the IUPAC R
Nomenclature for straight chain and branched alkenes, 3
cycloalkenes and simple diene
Name alkenes according to common name

Isomerism
Describes the constitutional, cis-trans and E-Z
isomerism for alkenes
A
S Physical Properties
C Explain the physical properties of alkenes

0
3
0
3
 C
Learning outcomes H
A
Reactions of Alkenes P
Describe the addition reactions of alkenes with T
hydrogen in the presence of catalyst, halogen (Cl2 or E
R
Br2) in inert solvent (CH2Cl2), halogen (Cl2 or Br2) in
water, hydrogen halides (HCl and HBr), acidified water 3
and concentrated sulphuric acid
Explain the formation of product according to the
Markovnikovs Rule
Write the Mechanism of electrophilic addition for
hydrogen halides and acidified water
Determine the product of reaction between alkene and
A hydrogen bromide in the presence of hydrogen
S peroxide/acid peroxide according to anti-Markovnikovs
C Rule
Describe the oxidation reactions of alkenes with dilute,
0 alkaline KMnO4 solution (Baeyers test), hot, acidified
3
0 KMnO4 solution and ozonolysis using O3 followed by
3 Zn, H2O or O3 followed by (CH3)2S
 C
Learning outcomes H
A
P
Identification Test for Alkenes T
Explain the identification test for alkenes compounds: E
Baeyers test using dilute, alkaline KMnO4 solution; R
bromine in CH2Cl2; and bromine water 3

A
S
C

0
3
0
3
 C
Introduction H
Alkenes A
hydrocarbons molecules with H2C CH2 P
carbon-carbon double bond (-C=C-) T
E
structure CH3 R
also referred as unsaturated
compounds or olefins
H2C C
3
composed at least one double bond CH3
in the carbon chain.

Cycloalkenes
Alkenes that contain ring structure
are unsaturated cyclic hydrocarbons
A called cycloalkenes
S Cycloalkenes contain at least one
C double bond in a ring
0
3
0
3
 C
Alkenes and cycloalkenes H
A
General Formula P
IUPAC Nomenclature T
Nomenclature of Alkenes E
Common Name R

Constitutional 3
Isomerism cis-trans
E-Z isomerism
Physical Properties
Addition Reactions
Markovnikovs Rule
Reactions of Alkenes
A Anti-Markovnikovs Rule
S Oxidation Reactions
C
Baeyers test
0
3 Identification Test Bromine in CH2Cl2
0
3 Bromine Water
 C
General Formula H
A
Alkenes General Example P
T
Formula
E
Alkenes with one double bond CnH2n C2 H 4 H2C CH2 R

3
C H8 CH
4
H3C CH CH3

Alkenes with two double bond CnH2n-2 C2C4H6 CH

H CH CH2

Cycloalkenes CnH2(n-m) C3 H 4

where n is the number of carbon atoms.

m represents the number of double bonds.
 C
H
A
P
Naming the Alkenes T
E
R

3
IUPAC Nomenclature
Common Name

A
S
C

0
3
0
3
 Naming the AlkenesCH
A
Alkenes are named with the suffix -ene P
T
E
R

A
S
C

0
3
0
3
 C
Naming the cycloalkenes
H
Nomenclature of cycloalkenes structures A
P
T
E
R

A
S
C

0
3
0
3
 C
Alkenes and cycloalkenes can be named by the H
following step A
P
T
Step 1: Name the longest carbon chain that contains E
double bond as a parent. R

3
hexene

Step 2: Number the carbon of parent chain from the

nearest double bond

hex-3-ene
A
S
C Step 3: Number the substituents according to the
position of double bond
0
3
0
3 2-methylhex-3-ene
 C
Step 4: If more than one double bond is present, H
A
number the carbon from the nearest double bond. P
Use the suffix diene (for two double bond). T
E
R

2-methylhex-1,3-diene 3

Step 5: Use E/Z (or cis/trans) to indicate the isomer

structure

A
S cis-2,3-methylhex-1,3-diene
C

0
3
0
3
 C
EXAMPLE H
A
Write the IUPAC name for this alkene structure P
T
E
R
SOLUTION
3
Step 1: Name the longest carbon chain

heptene

A
S Step 2: Number the chain from the nearest double bond
C

0 hept-3-ene
3
0 Step 3: Number the substituents
3
 C
EXAMPLE H
Write the IUPAC name for this cycloalkene structure A
P
T
E
R

3
SOLUTION
Step 1: Name the longest carbon chain
CH3
5
CH3
4 1
A 2
3
S
C Step 2: Number the ring from the nearest double bond

0 Step 3: Number the substituents

3
0
3 1,5-dimethylcyclopent-1-ene
 C
Common Name for Alkene Molecules H
A
IUPAC Common name Chemical Structures
P
T
eth-1-ene ethylene
E
or
H2C CH2 R
ethene
3
H H
propylene
prop-1-ene
or C C
propene
H CH3

H H
2-methylbuta-1,3-diene isoprene
or H C C
A C C H
S 2-methyl-1,3-butadiene
C H CH3

0 isobutylene H3C CH2

methylprop-2-ene C
3 or
0 2-methylpropene CH3
3
 Isomer
Constitutional Isomers

Stereoisomers:
Conformational
Geometric
cis-trans
E-Z

PUSAT ASASI SAINS

 C
H
Isomerism A
Isomers are different compounds or chemical P
T
properties that have the same molecular formula. E
R
Constitutional Isomers
3
Constitutional isomers also known as structural
isomers have different molecular structures due to
different orientation or arrangement of atoms in the
molecules.

A
S
C

0
3
0
3
 Constitutional isomer C
H
A
P
T
E
R

A
S
C

0
3
0
3
 Constitutional isomer C
H
A
P
T
E
R

A
S
C

0
3
0
3
 C
H
Geometrical Isomers A
In alkenes, cis and trans isomers are possible in the P
present of double bond which is rigid, cannot rotate T
E
and has groups attached to the carbons of the R
double bond that are fixed relative to each other.
3
Cis-trans isomers occur when different groups are
attached to the double bond.

In a cis isomer, all the substituents groups are

attached on the same side of the double bond.
A
S In the trans isomer, the groups are attached on
C
opposite sides.
0
3
0
3
 C
Geometrical Isomers H
A
P
Molecular Formula Geometrical Isomer T
E
R
H

3
C H
H3C C

CH3
C4H8 cis-but-2-ene

A H
S
C C CH3
H3C C
0
3 H
0 trans-but-2-ene
3
 C
The E/Z Isomers H
A
P
For compounds with more than two substituents, E- T
Z notation is used instead of cis and trans. E
R

It is an extension of cis/trans notation that can be 3

used to describe double bonds having three or four
substituents.

If the two groups of higher priority are on

opposite sides of the double bond, the bond is
A assigned the configuration E.
S
C Meanwhile, if the two groups of higher priority are
0 on the same side of the double bond, the bond is
3 assigned the configuration Z.
0
3
 C
The E/Z Isomers H
A
P
T
E
1 1 If the groups of highest priority R

are on the same side of the 3

double bond, name the isomer Z
2 2

A
S 1 If the groups of highest priority
C are on the opposite side of the
double bond, name the isomer E.
0
3 1
0
3
 C
EXAMPLE H
A
P
Draw and naming a possible constitutional and T
E
geometrical isomers for C8H16: R

A
S
C

0
3
0
3
 C
SOLUTION H
A
Constitutional Isomers CH3 P
T
H3C HC H CH3 E
R
C C C C H
3
H H H H

2-metylhept-3-ene
Geometrical Isomers
H
H CH3 H H
A H C
S H C C H H
C C CH
C
CH H CH3 C C C CH3
0 CH3 H3C H H CH3
3 H
0 (2Z)-4-methylhept-2-ene (3E)-6-methylhet-3-ene
3
 C
H
A
P
T
E
R

Physical Properties 3

Physical State of alkenes

Boiling Points
Melting Points
A Solubility
S
C

0
3
0
3
 C
Physical Properties H
A
Each carbon atom in a C=C double bond is sp2 P
hybridized. T
The double bond consists of a bond and a bond. E
R
The bond from head-on overlap of sp2 orbitals and
the bond from side-on overlap of p orbitals. 3

The bond is more reactive and weaker than bond of

a -C=C-, making it easier to break.
As a result, alkenes undergo many reactions that
alkanes do not.
A
S
C

0
3
0
3
 C
Physical Properties H
A
P
The sp2 hybridization forms flat structure of T
alkenes with 120o bond angles. E
R
According to VSEPR theory, three groups in a
double bond are bonded at 120 angles. 3

120 oC

A
S
C Alkenes are flat, because the atoms in a double
0 bond lie in the same plane.
3 Under normal conditions, no rotation is possible
0 about the carbon-carbon double bonds.
3
 C
H
Physical State of Alkenes A
P
At room temperature, T
E
C2-C3 alkenes are colorless gases R
C4-C15 alkenes are colorless liquids
3
C15 and higher alkenes are solids

Except ethene, C2H4 all other alkenes are colorless

and odorless. Ethene has a sweet smell.

The intermolecular attractions become stronger

A
S with an increase in the size of the molecules.
C

0
3
0
3
 C
H
Physical State of alkenes A
P
Alkenes Physical State T
E
C2H4 R

C3H6 Gases 3

C4H8
C5H10
C6H12
C7H14
A Liquids
S C8H16
C
C9H18
0
3
C10H20
0
3
 C
H
Boiling Points A
P
Alkenes have low melting points and boiling points. T
Boiling points increase as the number of carbons E
R
increases because of increased surface area.
These are due to the attraction between the molecules 3
by induced dipole-induced dipole interaction called as
London dispersion forces.

The intermolecular attractions become stronger with an

increase in the number of carbon and the molecular
masses which increase the size of molecules.
A The size of the alkenes molecules are increase and the
S molecules are packed with weak intermolecular force in
C
liquid state.
0
Therefore, more energy needed to break the bonds
3 which lead to increase the boiling point.
0
3
 C
H
A
Boiling Points P
T
E
R

A
S
C

0
3
0
3
 C
Boiling Points H
A
P
Cis-isomers are more polar molecules and have higher T
boiling points when compared to the trans-isomers. E
R
In the cis isomer,
the two Csp3Csp2 bond dipoles reinforce each other, 3

yielding a small net molecular dipole.

In the trans isomer,

the two bond dipoles cancel.

A For example,
S cis-but-2-ene has a higher boiling point (4C) than trans-
C but-2-ene (1C).
0
3
0
3
 C
H
Boiling Points A
P
T
E
R

A
S
C

0
3
0
3
 C
H
Melting Points A
P
Melting point of any organic compound depends on T
E
the packing arrangement of molecules. R

Melting points increase as the number of carbons 3

increases.

A symmetrical molecule packed nicely in system and

hence melting point increases.

A
S
C

0
3
0
3
 C
H
Melting Points A
P
T
E
R

A
S
C

0
3
0
3
 C
H
Solubility A
P
Alkenes are non-polar compounds which are T
soluble in organic solvents and insoluble in water E
with densities less than 1g/ml. R

3
Because of non-polar nature of alkenes, they are
insoluble in water but soluble in non-polar solvents
like benzene, carbon tetrachloride and petroleum
ether, etc.

A
S
C

0
3
0
3
 C
H
A
P
Reaction of Alkenes T
E
R

Addition reaction with O2 3

Halogenation
Mechanism of Free Radical Substitution

PUSAT ASASI SAINS

 C
Reactions of Alkenes H
A
P
Alkenes contain a carbon-carbon double bond T
(-C=C-) structure which has the capability to E
R
form any chemical reactions.
3
The carbon-carbon double is easily converted
to other functional groups.

The unsaturation in hydrocarbons makes

them more reactive compare to saturated
A hydrocarbons.
S
C This is due to the presence of bonds in
0 multiple bonds.
3
0
3
 C
H
A
P
T
Addition Reaction E
R
Alkenes are unsaturated compounds contain double 3
bonds which can undergo the addition reaction with
hydrogen in the presence of catalyst;
halogen (Cl2 or Br2) in inert solvent (CH2Cl2);
halogen (Cl2 or Br2) in water;
hydrogen halides (HCl and HBr);
acidified water; and
A
S concentrated sulphuric acid.
C

0
3
0
3
 C
H
Addition of Hydrogen to an Alkene A
P
T
Unsaturated alkenes can be converted into E
saturated alkanes by the hydrogenation process. R

3
Hydrogenation is the addition of a molecule of
hydrogen (H2) to a carbon-carbon double bond to
produce an alkane.

In this reaction, the double bond is broken, and

form two new C-H single bonds.
A
S
C This reaction is usually catalyzed by a nickel (Ni),
palladium (Pd) or platinum (Pt) catalyst.
0
3
0
3
 C
H
Hydrogenation Reaction of Alkenes A
P
H H H H T
c a ta ly s t E
C C + H H H C C H R
R H
R H 3
alkene alkane

Example:

H H
H H
A Ni
S C C + H H H2CH2CH3C C C H
C
H2CH2CH3C H H H
0
3 alkene alkane
0
3
 C
H
Addition of Halogen to an Alkene A
P
Chlorine (Cl2) or bromine (Br2) can be added to a T
E
double bond. R

3
This reaction, called halogenation, proceeds readily
and does not require a catalyst.

In general, an inert solvent, such as

dichloromethane (CH2CH2) or water used in the
addition reaction of alkenes with halogen.
A
S
C The reaction between an alkene and halogen
involves the breaking open of the alkenes double
0 bond and the inclusion of halogen in its structure
3
0 to form haloalkane.
3
 C
Halogenation Reaction of Alkenes H
A
P
H H X X
T
C C + X X E
H C C H R
R H
R H 3
alkene haloalkane

Example:
H H
H H
N i
A C C + Cl Cl H2CH3C C C H
S
C H2CH3C H Cl Cl
0 alkene haloalkane
3
0
3
 C
H
Addition of Halogen in Water to an Alkene A
P
T
Alkenes react spontaneously at room temperature E
with halogen in water (such as bromin water, R
HOBr) due to their unsaturated nature.
3

This reaction also called as halohydration of

alkenes is an electrophilic addition.

The reaction between an alkene and halogen water

involves the breaking open of the alkenes double
A bond to form haloalcohol.
S
C

0
3
0
3
 C
H
Halohydration Reaction of Alkenes A
P
H H OH H T
E
C C + X X H C C H + H X R
R H H 2O
R X
3
alkene haloalcohol

Example:
H H OH H
C C + Cl Cl H C C H + H Cl
A
S H3C H H 2O
CH3 Cl
C
alkene haloalcohol
0
3
0
3
 C
Addition of Hydrogen Halide to an Alkene H
A
P
Alkenes behave as nucleophile (Lewis bases) in polar T
reactions. E
R

The carbon-carbon double bond is electron-rich which 3

can donate a pair of electrons to hydrogen halide (HX)
which acts as an electrophile (Lewis acids).

The addition of hydrogen halide to an alkene also

known as electrophilic addition reaction.
A
S A donation of -electrons from the alkene creates a
C new C-H bond and an intermediate carbocation.
0
3 The carbocation then reacts with a nucleophile or
0 halide anion to form the product.
3
 C
H
Electrophilic Addition Reaction of Alkenes A
P
H H X H T
E
C C + H X H C C H R
R H
R H 3

Example:

H H Cl H
A C C + H Cl
S
H C C H
C H3C H
CH3 H
0
3
0
3
 C
H
Mechanism of Electrophilic Addition A
P
The reaction begins with an attack on the electrophile, T
HX, by the electron of the nucleophilic bond from E
the alkenes. R

3
Two electrons from the bond form a new bond
between the entering hydrogen and an alkene carbon.

The carbocation formed is an electrophile which can

accept an electron pair from nucleophilic X- ion to
form C-X bond and yield a product.
A
S
C

0
3
0
3
 C
H
Mechanism of Electrophilic Addition A
P
- T
X E
R

H H H
3
+
C C + H X H C C H
R H R H
alkenes hydrogen halide intermediate carbocation

A
S
C X H

0
H C C H
3
0
R H
3
 C
Markovnikovs Rule H
A
An unsymmetrical substituted alkenes form a single P
T
product rather than the mixture. E
R
In 1869, a Russian chemist, Vladimir Markovnikov
3
introduces the Markovnikovs Rule.

According to the Markovnikovs Rule, the hydrogen, H

attaches to the carbon with fewer alkyl substituents
and the X attaches to the carbon with more alkyl
substituents in the addition of HX to an alkene.
A
S
C H H X H
C C + H X H C C H
0
3 H2CH3C H CH3CH2 H
0
3
 C
Anti-Markovnikovs Rule H
A
The reaction between alkene and hydrogen bromide, P
HBr in the presence of hydrogen peroxide/acid T
E
peroxide is according to anti-Markovnikovs Rule.
R

Anti-Markovnikovs addition involves a free radical 3

additional mechanism.

H H H Br
w ith p e r o x id e
C C + H Br H C C H
R H R H
A
S
C

0
3
0
3
 C
Addition of Acidified Water to an Alkene H
A
A water molecule can be added to an alkene. P
T
E
This reaction known as hydration of alkenes, R
requires a trace of acid as a catalyst.
3

The catalyst in this case is a hydrogen ion (H+) from

an acid such as sulfuric acid or hydrochloric acid
and it initiates the reaction pathway, but is
regenerated at the end of the pathway so that there
is no net consumption of H+ in the reaction.
A
S H H + OH H
C
H
C C + H OH H C C H
0
R H
3 R H
0
3
 C
Mechanism of Electrophilic Addition in Acidified Water H
A
P
-
OH T
E
R
H H H
+ 3
C C + H OH H C C H
R H R H
C a r b o c a t i o n carbocation
intermediate in te r m e d ia te

A
S OH H
C
H C C H
0
3 R H
0
3
 C
Addition of Concentrated Sulfuric Acid to an Alkene H
A
Addition of concentrated sulfuric acid to alkenes P
leads to alkyl hydrogen sulphates which are soluble T
E
in the acid. R

The sulphate can be hydrolysed by heating with 3

water.

The addition follows Markovnikovs Rule.

H H H H
A C C + HO SO3H H C C OH
S
R H
C R H

0
3
0
3
 C
Oxidation Reaction H
A
P
Oxidation reactions involve the loss of electron, and a T
change in the oxidation state of the molecules E
involved with an increase of oxidation state. R

3
Carbon "loses" electrons by forming bonds with
elements that are more electronegative than it is.

Oxidising agents can be classified into the reagents

that contain a metal-oxygen bond such as KMnO4 and
A the reagents that contain an O-O bond such as O3.
S
C

0
3
0
3
 C
Oxidation of alkenes with cold KMnO4 solution H
A
P
Alkenes react with cold potassium permanganate T
(VII) solution (Baeyers reagent). E
R
Baeyers reagent is a deep purple color can be used 3
to differentiate between alkanes and alkenes groups
(Baeyers Test).

When the Baeyers reagent is added to an alkene,

the color change depends on whether the
potassium permanganate (VII) is used under acidic
A
S or alkaline conditions.
C

0
3
0
3
 C
Oxidation of alkenes with cold KMnO4 solution H
A
P
Under acidic conditions, the permanganate (VII) ions T
are reduced to manganese (II) ions. E
R
If the potassium permanganate (VII) solution is 3
acidified with dilute sulfuric acid, the purple solution
becomes colorless.
H H
- +
5 H2C CH2 + 2 H2O + 2 M nO 4 + 6 H 5H C C H + 2 M n 2+
OH OH
A purple colorless
S
C

0
3
0
3
 C
Oxidation of alkenes with cold KMnO4 solution H
A
P
Under alkaline conditions (by adding sodium T
E
carbonate solution), the purple solution of R
permanganate (VII) ions reduced to green
permanganate (VI) ions and then produces a dark 3
brown precipitate.

H H
- - 2-
H2C CH2 + 2M nO 4 + 2O H H C C H + 2M nO 4

purple OH OH green
A
S
C

0
3
0
3
 C
The Interaction of Manganate (VII) ions with Ethene H
A
P
Manganate (VII) ions are a strong oxidising agent, and T
in the first instance oxidise ethene to ethane-1,2-diol. E
R
H H
3
H2C CH2 + H2O + KM nO 4 H C C H
OH OH

A
S
C

0
3
0
3
 C
Oxidation of alkenes with cold KMnO4 solution H
Under mild conditions, KMnO4 can effect conversion A
P
of alkenes to glycols and producing a brown T
precipitate of manganese dioxide, MnO2. E
R

The reaction can also refer as hydroxylation 3

reactions.

It is, however, capable of further oxidizing the glycol

with cleavage of the carbon-carbon bond.

A
A cyclic manganese diester is an intermediate in
S these oxidations, which results in glycols formed
C by syn addition.
0
3 With addition of heat and/or more concentrated
0 KMnO4, the glycol can be further oxidized, cleaving
3
the C-C bond.
 C
Oxidation of alkenes with cold KMnO4 solution H
A
P
T
H E
R
H H
alkenes 3
H
+ O + M nO
H 3- H OH
2
O Mn OH
-
O O manganese dioxide
5- - O glycols
O Mn O (brown precipitate)
O

A
S
C

0
3
0
3
 C
Oxidation of alkenes with cold KMnO4 solution H
A
The general equation of oxidation of alkenes with P
cold KMnO4 solution occurs as follow: T
E
R
R' H H H
KM nO 4 3
C C R' C C H + M nO 2
-
H H O H
OH OH

A
S
C

0
3
0
3
 C
Oxidation of alkenes with hot concentrated acidified H
A
KMnO4 solution P
T
E
Alkenes react with hot, concentrated KMnO4 conditions R
produce ketones or carboxylic acid.
3

The product are known as carbonyl compounds

because they contain the carbonyl group, -C=O.

A
S
C

0
3
0
3
 C
Oxidation of alkenes with hot concentrated H
A
acidified KMnO4 solution P
T
Oxidative cleavage of glycol can occur if KMnO4 E
solution is warm or acidic or too concentrated. R

3
The acidified potassium permanganate (VII) solution
oxidises the alkene by breaking the carbon-carbon
double bond and replacing it with two carbon-
oxygen double bonds.

The carbonyl compound can also react with

A
S potassium manganite (VII).
C
Disubstituted carbons become ketones whereas
0
3 monosubstituted carbons become aldehydes, which
0 are further oxidized to produce carboxylic acids.
3
 C
Oxidation of alkenes with hot concentrated H
A
acidified KMnO4 solution P
T
R'' R'
R'' R' conc. M nO - E
4
C C R''' C C H R
heat
R''' H OH OH
3
glycol

R'' R'
C O + C H
R''' O

A ketones aldehydes
S
C
R'
0
O C
3
0 OH
3 carboxylic acids
 C
Oxidation of alkenes with ozone H
A
P
The reaction of an alkene with ozone (O3) to yield T
E
products of double-bond cleavage is called R
ozonolysis.
3
The ozonolysis reaction can occur using O3 followed
by Zn, H2O or O3 followed by (CH3)2S.

Both ketone and aldehyde reaction products can be

isolated using the ozonolysis reaction.
A
S
C
Ozonolysis can be used to synthesize aldehydes,
ketones, and carboxylic acids from alkenes, and it
0 can be used to break molecules into smaller pieces.
3
0
3
 C
H
Oxidation of alkenes with ozone A
P
T
R''' E
R'' R' O 3, C H 3O H H R
O
C C R' 3
o
- 60 C R'' O
H R''' O

(C H 3)2S

R'' R'''
A
S C R'
C
C O +
HO O
0
3 carboxylic acids ketones
0
3
 C
H
Identification Test for Alkenes A
P
T
Chemical tests have been developed to identify E
the functional groups presented in an unknown R

compound. 3

Alkenes compounds can be identified by using

Baeyers test using dilute,
alkaline KMnO4 solution,
bromine in CH2Cl2 and
A bromine water
S
C

0
3
0
3
 C
Baeyers test using dilute, alkaline KMnO4 solution H
A
Baeyers test can be used to identify unsaturated P
T
bonds but not for alkanes and aromatics. E
R
Baeyer's reagent, named after the German organic
chemist Adolf von Baeyer (1835-1917), is used in 3
organic chemistry as a qualitative test for the
presence of unsaturation.
Alkene is oxidized to a diol, which uses up the purple
permanganate solution and produces manganese
dioxide, a brown precipitate.
A
S R' H H H
C KM nO 4 M nO 2
C C + R' C C H +
( p u r p le s o lu tio n ) ( b r o w n s o lid )
0 H H OH OH
3 a lk e n e d io l
0
3
 C
Bromine in Methylene Chloride H
A
The bromine test is used to determine double -C=C- P
T
bonds structure in colorless organic compound. E
R
Bromine will add to the carbon-carbon double bond of
alkenes to produce dibromoalkane in the presence of 3
methylene chloride, CH2Cl2.
When an alkene is reacted with bromine, the red-brown
color of the bromine is immediately lost due to the
reaction of the bromine.
A H H Br H
S C H 2 C l2
C C C + Br Br H C C H
R H
0 R Br
3
0 a lk e n e re d -b ro w n c o lo r le s s
3
 C
Bromine water H
A
Alkenes react spontaneously with bromine water at P
T
room temperature due to their unsaturated nature. E
R
When alkenes come into contact with bromine
water, they cause it to the reddish-brown bromine is 3
decolourise.
A gaseous alkene like ethene, can bubble through
pure liquid bromine.
A liquid alkene can be shaken with liquid bromine
and decolourised the reddish-brown the color
A bromine.
S
H H Br H
C
C C + Br Br H C C H
0 R H
3 R Br
0 a lk e n e re d -b ro w n c o lo r le s s
3
 C
H
A
P
T
E
R

A
S
C

0
3
0
3