SK025 TOPIC 5.

2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

PREPARATION OF ALKENES – Dehydration of Alcohols

Reactants: Alcohol (ROH)
Conditions:
• concentrated sulphuric acid/ other strong acid
• heat or reflux
Type of reaction: Elimination reaction

EXAMPLE 1

PREPARATION OF ALKENES – Dehydrohalogenation of Alkyl Halide

Reactants: Alkyl Halide (Haloalkane, RX)
Conditions:
• base such as KOH, alcohol or alkoxide ion, RO‒
• heat or reflux
Type of reaction: Elimination reaction

EXAMPLE 2

DETERMINE MAJOR PRODUCT OF ELIMINATION REACTION

Saytzeff’s Rule
In an elimination reaction, the major product is the most stable alkene, commonly the
most highly substituted alkene

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

PREPARATION OF SYNTHETIC POLYMERS THROUGH ADDITION

POLYMERIZATION
INITIATOR:
▪ Homolysis of the weak O−O bond of the peroxide forms RO●, which then adds to a
molecule of monomer to form a carbon radical.
▪ Peroxide, ROOR is used as initiator in addition polymerization.

EXAMPLE:

POLYMER MONOMER EXAMPLE

polyethylene Uses: film, toys, bottles, plastic bags, container,

electrical insulation

polyvinylchloride
(PVC) Uses: pipe, siding, floor tile, gutters, clothing, toys

polystyrene Uses: packaging, toys, clear cups, egg cartons, coffee

cup, electrical components, parts of furniture

Teflon Uses: coating on cooking utensils, electrical

insulation, bearings
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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

REACTION OF ALKENES - Hydrogenation

Reactants: Alkene and Hydrogen gas
Conditions:
• inert solvent (example: CH2Cl2, CCl4)
Type of reaction: Electrophilic Addition reaction

EXAMPLE 3

REACTION OF ALKENES – Halogenation in Inert Solvent

Reactants: Alkene and Halogen (Cl2 or Br2)
Conditions:
• inert solvent (example: CH2Cl2, CCl4)
Type of reaction: Electrophilic Addition reaction

Vicinal di-halo compound

EXAMPLE 4

REACTION OF ALKENES – Halogenation in Water

Reactants: Alkene and Halogen in water (Cl2/H2O or Br2/H2O or Cl2 (aq) or Br2 (aq))
Type of reaction: Electrophilic Addition reaction

Halohydrin

EXAMPLE 5
Follow
Markovnikov’s
Rule
C=C with greater H
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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

MARKOVNIKOV’S RULE
In an addition reaction, H atom (or electrophile) is added to the C atom of the double bond
that contain greater number of H

REACTION OF ALKENES – Hydrohalogenation

Reactants: Alkene and HX (X: Cl or Br)
Type of reaction: Electrophilic Addition reaction

Haloalkane

EXAMPLE 6
Follow
Markovnikov’s
C=C with greater H Rule

REACTION OF ALKENES – Hydrohalogenation (HBr with peroxide)

Reactants: Alkene and HBr
Conditions: Peroxide, ROOR (example: H2O2, CH3OOCH3)
Type of reaction: Electrophilic Addition reaction
H atom attached to C=C with fewer H atoms
EXAMPLE 7
Follow
Anti−Markovnikov’s
C=C with fewer H Rule

REACTION OF ALKENES – Hydration

Reactants: Alkene and water (dilute H2SO4 (aq))
Conditions: acid catalyst (example: H2SO4)
Type of reaction: Electrophilic Addition reaction

Alcohol

EXAMPLE 8
C=C with greater H Follow
Markovnikov’s
Rule

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

REACTION OF ALKENES – Ozonolysis

Reactants: Alkene
Conditions: ozone followed by Zn, H2O
Type of reaction: Oxidation Reaction

Ketone Aldehyde
EXAMPLE 9: Produce a mixture of aldehyde and ketone

No H on C=C Got H on C=C

EXAMPLE 10: Produce Aldehyde only

Got H on C=C
EXAMPLE 11: Produce Ketone only

No H on C=C

Can be used to determine the structure of an unknown alkene

product of ozonolysis

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

REACTION OF ALKENES – Reaction with Hot Acidified KMnO4

Reactants: Alkene
Conditions: KMnO4, H+, heat
Type of reaction: Oxidation Reaction

Ketone Carboxylic acid

EXAMPLE 12: Produce Carboxylic Acid

Got one H on C=C

EXAMPLE 13: Produce Ketone

NO H on C=C

EXAMPLE 14: Produce CO2 and H2O

NO H on C=C Two H on C=C

Can be used to determine the structure of an unknown alkene

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

REACTION OF ALKENES – Reaction with Cold Dilute KMnO4

Reactants: Alkene
Conditions: dilute KMnO4, OH−, cold/ room temperature
Type of reaction: Oxidation Reaction/ Electrophilic Addition Reaction

Diol

EXAMPLE 15

OZONOLYSIS & REACTION WITH HOT ACIDIFIED KMnO4

(CYCLOALKENE)
EXAMPLE 16

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

OUTLINE SYNTHETIS
EXAMPLE 17
Outline the synthetic pathway for the formation of:
(a) 1,2-dibromocyclopentane from bromocyclopentane.

(b) 1-bromo-2-propanol from 1-propanol

(c) cyclopentene from cyclopentane

(d) 1-bromopropane from 2-bromopropane

(e) 2-methylbutane to 2-bromo-2-methylbutane

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

MIND MAP ALKANE & ALKENE

ELIMINATION
REACTION

Conc. H2SO4 CH3 KOH, CH3CH2OH

heat heat
H3C C CH2

Major + Minor
Br2 H2/Pt Cl2, CH2Cl2

ELECTROPHILIC ADDITION REACTION

uv Halogenation in inert solvent
Hydrogenation

FREE RADICAL SUBSTITUTION REACTION

Br2/ H2O
Hydrohalogenation Halogenation in water
H: HBr Br:
Br: OH:
Markovnikov’s Rule

HBr with peroxide

H: HBr/ H2O2 H2O/ H+
Hydration (Acidified Water)
Br:
H:
Anti-Markovnikov’s Rule
OH:

OXIDATION i. O3 KMnO4, H+
REACTION ii. Zn, H2O dilute KMnO4, OH‒, cold heat

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 SK025 TOPIC 5.2 PREPARATIONS & CHEMICAL PROPERTIES OF ALKENES | Nur Deena Khalid

Hydrogenation
MIND MAP ALKANES & ALKENES
H2/ Pt

conc. H2SO4

Hydrohalogenation
ELIMINATION REACTION
HCl
H+, Cl-
Dehydration of Alcohols H:
Cl:
KOH, ethanol

HBr/ H2O2
anti Markovnikov’s
Dehydrohalogenation of Haloalkanes H+, Br- H:
Br:

KOH, ethanol ELECTROPHILIC Br2, CH2Cl2

ADDITION REACTION

Halogenation
Major product
SUBSTITUTION REACTION

COMBUSTION REACTION Ozonolysis

uv Br2 i. O3
OXIDATION REACTION
FREE RADICAL

excess O2 Cl2/ H2O

ii. Zn, H2O
Cl+, OH-
Cl:
limited O2 OH:
Hot acidified KMnO4
very limited
O2 KMnO4, H3O+

Hydration
Halogenation of Alkanes H2O/ H+
heat
H+, OH- H:
dilute KMnO4, OH‒ OH:
cold 10

Dilute alkaline KMnO4