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ALKENES
 Alkenes
• General formula : CnH2n , n ≥ 2
• Functional group : carbon-carbon double bond,
C=C
• Is an unsaturated hydrocarbon.
• The term "unsaturated" is used to designate a
compound which contains double or triple
bonds.

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• An alkenes is a hydrocarbon containing at least
one double bonds.
• Examples of unsaturated compounds are
ethene, C2H4 ,benzene, C6H6.

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 IUPAC Nomenclature

• IUPAC nomenclature for:

i. Straight chain (C2-C10)
ii. Branched alkenes (C4-C10)
iii. Cyclic alkenes (C4-C6)

• Following are the rules for IUPAC nomenclature

of alkenes:

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1. Determine the parent name by selecting the longest
chain that contains the double bond and change the
ending of the name of the alkane of identical length
from -ane to -ene.

ethene

propene

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2. Number the chain from the end closest to the
double bonds. Place the numbers giving the
locations of the double bonds in front of the
parent name.

1 2 3 4
1-butene

1 2 3 4 5 6 7 8

3-octene (not 5-octene)

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3. Indicate the locations of the substituent groups
by the numbers of the main-chain carbon atoms
to which they are attached.

1 2 3 4

2-methyl-2-butene (not 3-methyl-2-butene)

1 2 3 4 5 6

2,5-dimethyl-2-hexane (not 2,5-dimethyl-4-hexene) 7

4. The double bond in cycloalkenes must be numbered
as 1 and 2 and that also gives the substituent groups
the lower numbers at the first point of difference.

1-methylcyclopentene
(not 2-Methylcyclopentene)

3,5-dimethylcyclohexene
(not 4,6-Dimethylcyclohexene)

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5. When two identical groups are;
- on the same side – cis isomer.
- on the opposite side – trans isomer.

cis-1,2-dichloroethene trans-1,2-dichloroethene

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Example :
Give the IUPAC names for the following alkenes

1)

2)

3)

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4)

5)

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 Synthesis or preparation of alkene

• An alkene can be prepared through :

❑ Dehydration of alcohol

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 Dehydration of alcohols

• Alcohols react with strong acids (conc. H2SO4 or conc.

H3PO4) in the presence of heat to form alkenes and
water.
• General equation :

• H and OH are removed from the adjacent carbon atoms.

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• Concentrated sulphuric acid (H2SO4) or phosphoric acid
(H3PO4) as acidic catalysts and dehydrating agents.
• When the dehydration of an alcohol produces a mixture
of alkenes, the major product obtained can be predicted
by the Saytzeff’s rule.
• Saytzeff’s rule state that the major product in elimination
is the most stable alkenes which has the most highly
substituted double bond.

Minor product Major product

(more
substituents)
 Example :
Draw the product of the following reactions. Identify the
major product if it forms mixture of alkenes.

1.

2.

3.

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4.

5.

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Example :

Dehydration of 2-methyl-2-butanol able to form a mixture of

alkenes.
i. Write the chemical equation for the reaction.
ii. Identify the major product. State the rule that we use to
identify the major product.

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 Chemical reaction of alkenes

• Alkenes are more reactive compared to alkanes.

• Alkanes have carbon-carbon single bonds (σ bonds)
while alkenes have carbon-carbon double bonds (π
bonds).
• The double bond is a site of high electron density
• Therefore, the characteristic reaction of alkenes is
addition.

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• 4 addition reactions of alkenes:
a. Hydrogenation : Addition of hydrogen in presence of catalyst
b. Halogenation :
i. Addition of halogen (Cl2 or Br2) in inert solvent (CH2Cl2)
ii. Addition of halogen (Cl2 or Br2) in water
c. Hydrohalogenation : Addition of hydrogen halides (HCl
or HBr) – with peroxide & without
peroxide
d. Hydration : Addition of acidified water

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 (a) Hydrogenation : Addition of H2

• The reaction of an alkene with hydrogen in the

presence of catalyst (platinum, nickel and palladium)
forms an alkane.
• General equation :

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Example :
Draw the products of the following reactions.

1.

2.

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 (b) Halogenation : Addition of X2

• Points need to consider for halogenation of alkene:

a) Solvent of halogen ( inert solvent or water)
b) Symmetry of the structure

• 2 conditions:
i. Addition of halogen (Cl2 or Br2) in inert solvent (CH2Cl2)
ii. Addition of halogen (Cl2 or Br2) in water

• Bromination of alkene in inert solvent or in water can be

used to distinguish alkenes from alkanes (unsaturation
test).
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(i) In inert solvent
• Alkenes react rapidly with chlorine or bromine in
CH2Cl2 or CCl4 at room temperature to form vicinal
dihalides.
• General equation:

• A vicinal dihalide has two halogen atoms bonded to

adjacent carbon atoms.
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 Example :
Draw the products of the following reactions.

1.

2.

3.

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(ii) In water (H2O)

• In water, chlorine or bromine react with alkenes to form

vicinal halohydrins.
• General equation:

• A halohydrin is a compound that have a halogen and a

hydroxyl group on adjacent carbons.

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• Examples of halogenation in water of symmetrical alkenes:

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• For the unsymmetrical alkenes, the halogen atom is
attached to the carbon atom that has more hydrogen
atoms.
• Example:

H
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 (c) Hydrohalogenation : Addition of HX

∙ Hydrogen halides (HBr or HCl) is added to the double

bond of alkenes to form haloalkanes.
∙ General equation :

haloalkanes

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• Example of hydrohalogenation of symmetrical alkenes:

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∙ The addition of HX to unsymmetrical alkenes follows
Markovnikov’s rule in order to determine the major
product.
∙ Markovnikov’s Rule state that in the addition of HX to
an alkenes, the hydrogen atom is added to the carbon
atom of the double bond that has the greater number
of hydrogen atoms.

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Example :
The addition of HBr to propene, could conceivably lead to
either 1-bromopropane or 2-bromopropane.The major
product, however, is 2-bromopropane. Explain.

2-bromopropane 1-bromopropane
Markovnikov’s rule:
hydrogen atom is (Major product)
added to the carbon
atom of the double
bond that has the
greater number of
hydrogen atoms.
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 Example :
Draw the major product for the following reactions.

1.

2.

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 Mechanism of addition of a HX to an alkene

• Mechanism of addition of hydrogen halide to alkene

involve 2 steps:
i. Formation of carbocation
ii. Nucleophilic attack

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Example :

Write the mechanism for the following reaction.

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Step 1: Formation of carbocation

• The π electrons of the alkene form a bond with a proton

from HX to form a carbocation and a halide ion.

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Step 2: Nucleophilic attack

• The halide ion reacts with the carbocation by donating an

electron pair. The result is an alkyl halide.

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Example :

Write the mechanism for the following reaction.

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 Addition of HBr to Alkenes with
presence of peroxide (anti-Markovnikov)

∙ When alkenes are treated with HBr in the presence of

peroxides, ROOR (eg: H2O2) the addition occurs in
an anti-Markovnikov manner.
∙ The hydrogen atom of HBr attached to the doubly
bonded carbon with fewer hydrogen atoms.
∙ General equation :

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 Example :
Draw the products of the following reactions.

1.

2.

3.

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 (d) Hydration : Addition of acidified water

∙ The acid-catalyzed addition of water to the double bond

of an alkene (hydration of an alkene) is a method for the
preparation of low molecular weight alcohols.
∙ The acid most commonly used to catalyse the hydration
of alkenes are dilute solution of sulphuric acid(H2SO4)
and phosphoric acid(H3PO4).
∙ The addition of water to the double bond follows
Markovnikov’s rule.
∙ General equation:

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Example 16 :
Draw the products of the following reactions.

1.

2.

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 Unsaturation test

• Unsaturation test is used to differentiate alkenes from

alkanes.
• Three unsaturation test:
i. Baeyer’s test (using cold, dilute, alkaline solution
of KMnO4)
ii. Bromine test (Reaction with bromine in CH2Cl2 )

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 (i) Baeyer’s test
• Baeyer’s test is an unsaturation test for an alkene to
determine the presence of C=C in which the purple colour
of the KMnO4 decolourised, and the brown precipitate of
MnO2 is formed.

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Test : Baeyer’s test
Reagent : cold, dilute, alkaline solution of KMnO4

Alkene

Observation: Purple colour of KMnO4 decolourised and

brown precipitate formed.

Alkane

No observable
change
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 (ii) Bromine test
• Bromination of alkene in inert solvent can be used to
distinguish alkenes from alkanes (unsaturation test).
• Bromine is used to determine the presence of carbon-
carbon double bonds.
• When bromine is added to an alkene, the reddish
brown color of the bromine disappears almost
instantly as long as the alkene is present in excess.

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Test : Bromination in inert solvent
Reagent : Br2 in CCl4

Alkene

Observation : The reddish brown color of bromine

decolourised

Alkane
No observable
change
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Example :
Suggest a chemical test to differentiate butane from
2-butene. State the observations and write all the reaction
equations involved.

Answer:

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