ORGANIC CHEMISTRY

CHM 207
CHAPTER 3
ALKENES
Upon completion of this topic, students should be able to:

1. Interpret the properties of alkenes compounds as well as it’s IUPAC

name, chemical structure, properties, preparation, reaction &
mechanism (LO1, C3).

2. Explain the properties of alkenes compounds as well as it’s IUPAC

name, chemical structure, properties, preparation, reaction of
alkenes : Addition, Combustion, Oxidation, Polymerization (LO2,
C6).

3. Write comprehensive information on the uses of alkenes compounds

in commercial industrial applications (LO3, A4).
 Nomenclature

Structures and
physical
properties
Addition
Preparation of
alkenes
Subtopics Combustion
Reactions of
alkenes
Oxidation
Unsaturation
tests
Polymerization

Uses
 ALKENES
• Also called olefins
• Contain at least one carbon-carbon double bond
(C=C)
• General formula, CnH2n (n=2,3,…)
• Classified as unsaturated hydrocarbons
(compound with double or triple carbon-carbon
bonds that enable them to add hydrogen atoms.
• sp2-hybridized
• For example:
C2H4 - ethylene
CH2 CH2
Naming
Alkenes
 IUPAC RULES
RULE 1. Select the longest continuous carbon chain that
contains a double bond.

This chain
This chain
contains 6 C
contains 8
atoms
C atoms
wrong correct

RULE 2. Name this compound as you would an alkane, but

change –ane to –ene for an alkene.

- The chain contain 8 C, therefore, name the parent compound octene.

RULE 3. Number the carbon chain starting with the end
nearer to the double bond.

Use the smaller numbes on the double-bonded carbon to

indicate the position of the double bond. Place this number in
front of the alkene name.
This end of the chain is closest to the
double bond. Begin numbering here.
4 3 2 1

The name of the parent compound is 1-octene.

RULE 4. Branched chains and other groups are treated as in
naming alkanes. Name the substituent group, and designate its
position on the parent chain with a number.

The ethyl group is attached to carbon 4.

4 3 2 1

IUPAC name : 4-ethyl-1-octene

 NEW IUPAC NAMES
• Placing numbers (location of double bond) before the
part of the name –ene.
• Example:
1 2 3 4 1 2 3 4 5 6
CH2 C CH2 CH3 CH3 C C CH2 CH2 CH3
H H H
Old naming system: 1-butene Old naming system: 2-hexene
New naming system: but-1-ene New naming system: hex-2-ene

CH3
1 2 3 4
CH2 C C CH3
H H
Old naming system: 3-methyl-1-butene
New naming system: 3-methylbut-1-ene
• A compound with more than one double bond.
- Two double bond: diene
- Three double bond: triene
- Four double bond: tetraene
* Numbers are used to specify the locations of the double bonds.

1 2 3 4 7 6 5 4 3 2 1
CH2 C C CH2 CH3 C C C C C CH2
H H H H H H H
IUPAC names: 1,3-butadiene 1,3,5-heptatriene
new IUPAC names: buta-1,3-diene hepta-1,3,5-triene

1 2
8 3

7 4
6 5
IUPAC names: 1,3, 5, 7-cyclooctatetraene
new IUPAC names: cycloocta-1,3,5,7-tetraene
 ALKENES AS SUBSTITUENTS

• Alkenes names as substituents are called alkenyl groups.

• Can be named systematically as ethenyl, propenyl, etc. or by

common names such as vinyl, ally, methylene and phenyl groups.

CH2 -CH=CH2 -CH2-CH=CH2

methylene group vinyl group allyl group
(methylidene group) (ethenyl group) (2-propenyl group)

CH=CH2
CH2 CHCHCH2CH CH2
3-methylenecyclohexene IUPAC name: 3-vinyl-1,5-hexadiene
New IUPAC name: 3-vinylhexa-1,5-diene
 CYCLOALKENES

• Contains C=C in the ring

cyclopropene cyclobutene cyclopentene cyclohexene

• Nomenclature of cycloalkenes:
- Similar to that alkenes
- Number the cycloalkane so that the double bond is between C1 and
C2 and so that the first substituent has as low a number as
possible.
* Double bond always between C1 and C2.
6 1
CH3 5 6 2 CH2CH3
5 1 4 1
4 2 5 3
3 2 4
3
1-methylcyclohexene 1,5-dimethylcyclopentene IUPAC name: 2-ethyl-1,3-cyclohexadiene
New IUPAC name: 2-ethylcyclohexa-1,3-diene
 NOMENCLATURE OF cis-trans ISOMERS

H3C CH2CH3 H3C H

C C C C
H H H CH2CH3

cis-2-pentene trans-2-pentene

• cis – two particular atoms (or groups of atoms) are

adjacent to each other
• trans – the two atoms (or groups of atoms) are
across from each other
 Exercise 3.1

1) Give IUPAC name for the following 2) Draw the structural formulae
alkenes: for the following:

a)
a)
b)

c)
b)
d)

e)

c) f)
Answer - Exercise 3.1
Answer - Exercise 3.1
Answer - Exercise 3.1
Answer - Exercise 3.1
 Physical
Properties
of Alkenes
i) Boiling points and densities
ii)Polarity
 i. Boiling points and densities

- Most physical properties of alkenes are similar to those

alkanes.

- Example: the boiling points of 1-butene, cis-2-butene, trans-

2-butene and n-butane are close to 0oC.

- Densities of alkenes: around 0.6 or 0.7 g/cm3.

- Boiling points of alkenes increase smoothly with molecular

weight.

- Increased branching leads to greater volatility and lower

boiling points.
 ii. Polarity

- alkenes are relatively nonpolar.

- alkenes insoluble in water but soluble in non-polar

solvents such as hexane, gasoline, halogenated solvents
and ethers.

- alkenes slightly more polar than alkanes because:

i) electrons in the pi bond is more polarizable
ii) the vinylic bonds tend to be slightly polar
 Preparation
of Alkenes
i) Dehydration of alcohols
ii) Dehydrohalogenation of
haloalkanes
• Alkenes can be prepared in the following ways:

i. Dehydration of alcohols

conc. H2SO4
R-CH2-CH2-OH R-CH=CH2 + H2O

ii. Dehydrohalogenation of haloalkanes

NaOH/ethanol
R-CH2-CH2-X R-CH=CH2 + HX
reflux

NaOH can be replaced by KOH

 • Saytzeff rule:
- A reaction that produces an alkene would favour the
formation of an alkene that has the greatest number of
substituents attached to the C=C group.
Dehydration of alcohols
H+
CH3CH2-CH=CH2 + H2O
CH3CH2-CH-CH3 1-butene
+
OH H
CH3CH=CH-CH3 + H 2O
2-butanol
2-butene
major product

Dehydrohalogenation of haloalkanes
CH3CH-CH-CH2 alcohol CH3CH2CH=CH2
KOH CH3CH=CH-CH3
reflux
H Br H 2-butene
1-butene
2-bromobutane (major product)
• Saytzeff rule:
- A reaction that produces an alkene would favour the
formation of an alkene that has the greatest number of
substituents attached to the C=C group.
Dehydrohalogenation of haloalkanes

CH3CH-CH-CH2 alcohol CH3CH2CH=CH2

KOH CH3CH=CH-CH3
reflux
H Br H 2-butene
1-butene
2-bromobutane (major product)
• Saytzeff rule:
- A reaction that produces an alkene would favour the
formation of an alkene that has the greatest number of
substituents attached to the C=C group.
Dehydration of alcohols
H+
CH3CH2-CH=CH2 + H2O
CH3CH2-CH-CH3 1-butene
+
OH H
CH3CH=CH-CH3 + H 2O
2-butanol
2-butene
major product
 REACTIVITY OF ALKENES
Alkenes are more reactive than alkanes because:

i) A carbon-carbon double bond consists of a σ and a π bond. It

is easy to break the π bond while the σ bond remains intact.
ii) The π electrons in the double bond act as a source of
electrons (Lewis base). Alkenes are reactive towards
electrophiles which are attracted to the negative charge of
the π electrons.

iii) π bond will broken, each carbon atom becomes an active site
which can form a new covalent bond with another atom. One
π bond is converted into 2 σ bonds.
QUICK CHECK

1) State the Saytzeff rule.

2) By using the Syatzeff rule, draw the structure for the

major product obtained from dehydration of the
following alcohol:

a) CH3 b) OH
CH3CHCHCH3
CH2CH3
OH
ANSWER - QUICK CHECK
ANSWER - QUICK CHECK
ANSWER - QUICK CHECK
Reaction
of
Alkenes
i) Addition reaction
ii) Combustion of alkenes
iii) Oxidation
iv) Polymerization
 REACTIONS OF ALKENES
i) Addition reaction:
a) Addition of hydrogen (Catalytic hydrogenation)
b) Addition of halogens
- In inert solvent
- In water / aqueous medium
c) Addition of hydrogen halides
d) Addition reaction with concentrated sulfuric acid: hydration of
alkenes
e) Addition reaction with acidified water (H3O+): hydration of alkenes
ii) Combustion of alkenes
iii) Oxidation: iv) Polymerization
a) Epoxidation
b) Hydroxylation
c) Ozonolysis
 i) Addition reaction
a) Addition of hydrogen (Catalytic hydrogenation):
- hydrogenation: addition of H to a double bond and triple bond to
yield saturated product.
- alkenes will combine with hydrogen in the present to catalyst to
form alkanes.

Pt or Pd
C C H H o C C
25-90 C
H H
- Plantinum (Pt) and palladium (Pd) – Catalysts
- Pt and Pd: temperature 25-90oC
- Nickel can also used as a catalyst, but a higher temperature of 140oC
– 200oC is needed.
EXAMPLES:
Pt
H2C CH2 H2 H3C CH3
low pressure ethane
ethylene

Pt
CH3CH2CH2CH2CH CH2 H2 CH3CH2CH2CH2CH2CH3
low pressure
hexene hexane
b) Addition of halogens:

i) In inert solvent:
- alkenes react with halogens at room temperature and in dark.
- the halogens is usually dissolved in an inert solvent such as
dichloromethane (CH2Cl2) and tetrachloromethane (CCl4).
- Iodine will not react with alkenes because it is less reactive than
chlorine and bromine.
- Fluorine is very reactive. The reaction will produced explosion.

inert solvent
C C X X C C
X X
X X = halogen such as Br2 or Cl2
Inert solvent = CCl4 or CH2Cl2
EXAMPLES:

H H inert solvent (CCl4) H H

H C C H Br Br H C C H
ethene Br Br
1,2-dibromoethane

* the red-brown colour of the bromine solution will fade and the
solution becomes colourless.

Br
CCl4
Br2
Br
cyclohexene
1,2-dibromocyclohexane

CCl4 Cl Cl
CH3CH=CH2 Cl2 CH3CH CH2
propene 1,2-dichloropropane
b) Addition of halogens:

ii) In water / aqueous medium:

- chlorine dissolves in water to form HCl and chloric (l) acid
(HOCl).
Cl2 (aq) + H2O(l) HCl(aq) + HOCl (aq)

- same as bromine
Br2 (aq) + H2O(l) HBr(aq) + HOBr(aq)

* Reaction of alkenes with halogens in water/ aqueous solution (eg.

chlorine water and bromine water) produced halohydrins (an alcohol
with a halogen on the adjacent carbon atom).
 EXAMPLES:

H 2O
CH3CH=CH2 + Br2 CH3 CH CH2 CH3 CH CH2
OH Br Br Br
propene
1-bromo-2-propanol 1,2-dibromopropane
(major product) (minor product)
* Br atom attached to the carbon atom of the double bond which has the greater
number of hydrogen atoms.

Cl2, H2O CH3 CH2 CH CH2

CH3CH2CH=CH2
OH Cl
1-butene
1-chloro-2-butanol
c) Addition of hydrogen halides:

- Addition reaction with electrophilic reagents.

- Alkenes react with hydrogen halides (in gaseous state or in aqueous
solution) to form addition products.
- The hydrogen and halogen atoms add across the double bond to
form haloalkanes (alkyl halides).
- General equation:

H X
C C HX C C

alkene haloalkane

- Reactivity of hydrogen halides : HF < HCl < HBr < HI

* Reaction with HCl needs a catalyst such as AlCl3
AlCl3
H2C CH2 HCl CH3CH2Cl

EXAMPLES:

H-I I
cyclopentene iodocyclopentane

Br
CH3CH=CHCH3 + H-Br CH3CH2CHCH3
2-butene 2-bromobutane
 MARKOVNIKOV’S RULE
• There are 2 possible products when hydrogen halides react with an
unsymmetrical alkene.
• It is because hydrogen halide molecule can add to the C=C bond in
two different ways.

H H H H
CH3 C C H H-I CH3 C C H
H I
1-iodopropane

H H H H
CH3 C C H H-I CH3 C C H
I H
2-iodopropane
(major product)
Markovnikov’s rules:

- the addition of HX to an unsymmetrical alkene,

the hydrogen atom adds to the carbon atom (of
the double bond) that already has the greater
number of hydrogen atoms.
Mechanism of electrophilic addition reactions:
- C=C : electron rich part of the alkene molecule
- Electrophiles: electron-seeking
Step 1: Formation of carbocation.
Attack of the pi bond on the electrophile to form carbocation.

δ+ δ-
C C E Y C C Y-

E
carbocation
Step 2: Rapid reaction with a negative ion.
The negative ion (Y-) acts as nucleophile and attacks the positively
charged carbon atom to give product of the addition reaction.

C C Y- C C
E E Y
 ADDITION OF HYDROGEN HALIDES TO
UNSYMMETRICAL ALKENES AND
MARKOVNIKOV’S RULE

CH3CHCH2
3 2 1 H Cl
CH3CH=CH2 HCl
1-chloropropane
Propene
CH3CHCH2
Cl H
2-chloropropane
(major product)
according to Markovnikov's
rules
MECHANISM:

Step 1: Formation of carbocation

H H H H H H H H
H Cl H C C C H or H C C C H Cl-
CH3 C C H
H H H H
less stable carbocation more stable carbocation
o
(1 carbocation) (2o carbocation)

o o
- 2 carbocation is more stable than 1 carbocation.
o
- 2 carbocation tends to persist longer, making it more likely to combine with
-
Cl ion to form 2-chloromethane (basis of Markovnikov's rule).

Step 2: Rapid reaction with a negative ion

H H H H H H
H C C C H Cl- H C C C H
H H H Cl H
2-chloromethane (major product)
d) Addition reaction with concentrated sulfuric acid: hydration of
alkenes

- the alkene is absorbed slowly when it passed through

concentrated sulfuric acid in the cold (0-15oC).

- involves the addition of H atom and HSO4 group across the

carbon-carbon double bond.

- follows Markovnikov’s rule.

 H H H H
H C C H H OSO3H H C C H
(H2SO4)
H OSO3H
ethyl hydrogensulphate
(CH3CH2HSO4)
When the reaction mixture is added to water and warmed,
ethyl hydrogensulphate is readily hydrolysed to ethanol

CH3CH2OSO3H + H-OH CH3CH2OH + H2SO4

(H2O)

*ethene reacts with concentrated H2SO4 to form ethanol*

or

*alkene reacts with concentrated H2SO4 to form alcohol*

e) Addition reaction with acidified water (H3O+): hydration of alkenes

• Hydration: The addition of H atoms and –OH groups from water

molecules to a multiple bond.
• Reverse of the dehydration reaction.
• Direct hydration of ethene:
- passing a mixture of ethene and steam over phosphoric (v) acid
(H3PO4) absorbed on silica pellets at 300oC and a pressure of 60
atmospheres.
- H3PO4 is a catalyst.
H3PO4
CH2=CH2 (g) H2O (g) o CH3CH2OH (g)
300 C, 60 atm
ethene ethanol

H OH
H2O H+
C C C C
alkene alcohol
• Markovnikov’s rule is apply to the addition of a water molecule
across the double bond of an unsymmetrical alkene.
• For examples:
CH3 CH3
+
CH2 H OH H
CH3 C CH3 C CH2
25oC
2-methylpropene
OH H
tert-butyl alcohol

CH3CH=CH2 + H2O CH3CHCH3

propene H+ OH
2-propanol
H+ = catalyst
MECHANISM OF ACID CATALYSED HYDRATION OF ALKENES

Step 1: Protonation to form carbocation

H H H H H
+
CH3 C C H H H C C C H
H H
more stable carbocation
(2o carbocation)

Step 2: Addition of H2O to form a protonated alcohol

H H H
H C C C H H CH3CHCH3
O
H H O H
H
H

Step 3: Loss of a proton (deprotonated) to form alcohol

CH3CHCH3
CH3CHCH3 +
O H H
OH
H H+ = catalyst
 ANTI-MARKOVNIKOV’S RULE: FREE RADICAL
ADDITION OF HYDROGEN BROMIDE

• When HBr is added to an alkene in the absence of peroxides it obey

Markovnikov’s rule.

• When HBr (not HCl or HI) reacts with unsymmetrical alkene in the
presence of peroxides (compounds containing the O-O group) or
oxygen, HBr adds in the opposite direction to that predicted by
Markovnikov’s rule.

• The product between propene and HBr under these conditions is 1-

bromopropane and not 2-bromopropane.
peroxide
CH3CH=CH2 HBr CH3CH2CH2Br
H2O2
1-bromopropane
H Br (major product)
anti-Markovnikov's orientation
• Anti-Markovnikov’s addition:

- peroxide-catalysed addition of HBr occurs through a

free radical addition rather than a polar electrophilic
addition.

- also observed for the reaction between HBr and

many different alkenes.

- not observed with HF, HCl or HI.

 Formation of anti-Markovnikov alcohol
• Alkenes goes to hydroboration reaction to form anti-
Markovnikov alcohol.
H2O2, -OH
C C B2H6 C C
H OH
anti-markovnikov

examples:
H2O2, -OH
CH3CH=CH2 B 2H 6 CH3CHCH2-OH
propene propanol

CH3 H2O2, -OH

CH3
B 2H 6
CH3 C CH2 CH3 CH CH2 OH
isobutylene isobutyl alcohol

CH3 CH3
H2O2, -OH
B2H6 CH3CHCHCH3
CH3 CH C CH3
2-methyl-2-butene OH
3-methyl-2-butanol
 ii) Combustion of alkenes

▪ The alkenes are highly flammable and burn readily

in air, forming carbon dioxide and water.
▪ General equation of combustion of alkenes:
C2H4 + 3O2 → 2CO2 + 2H2O

▪ For example, ethene burns as follows :

C2H4 + 3O2 → 2CO2 + 2H2O
 iii) Oxidation

• Oxidation: reactions that form carbon-oxygen

bonds.

• Oxidation reaction of alkenes:

a) Epoxidation
b) Hydroxylation
c) Ozonolysis
 a) Epoxidation of alkenes

• Epoxide / oxirane: a three-membered cyclic ether.

O O O
C C C C R C OH
R C O O H

alkene peroxyacid epoxide (oxirane) acid

• Examples of epoxidizing reagent:

O O H
O
Cl O
CH3 C O O H C O OH O

peroxyacetic acid peroxybenzoic acid m-chloroperoxybenzoic acid

(PhCO3H) (MCPBA)
Examples:
MCPBA
o
O
CH2CI2, 25 C
cyclohexene 1,2-epoxycyclohexane

MCPBA
o
O
CH2CI2, 25 C

cycloheptene 1,2-epoxycycloheptane
b) Hydroxylation of alkenes

• Hydroxylation:
- Converting an alkene to a glycol requires adding a hydroxyl
group to each end of the double bond.
• Hydroxylation reagents:
i) Osmium tetroxide (OsO4)
ii)Potassium permanganate (KMnO4)

C C OsO4 H2O2 C C
(or KMnO4, -OH) OH OH
glycol
 Examples:
KMnO4 (aq), OH-
CH2 CH2 CH2 CH2 MnO2
cold, dilute
ethene OH OH
1,2-ethanediol

KMnO4 (aq), OH-

CH3 CH CH2 CH3 CH CH2 MnO2
cold, dilute
propene OH OH
1,2-propanediol

* Also known as Baeyer’s test

 c) Ozonolysis of alkenes

• Ozonolysis:
- The reaction of alkenes with ozone (O3) to form an ozonide, followed by
hydrolysis of the ozonide to produce aldehydes and /or ketone.

- Widely used to determine the position of the carbon-carbon double bond.

- Ozonolysis is milder and both ketone and aldehydes can be recovered

without further oxidation.

R R' R O R' (CH3)2S R R'

C C O3 C C C O O C
R O O H or H2O, Zn/H+
R H R H
ozonide ketone aldehyde
 EXAMPLES:

i) O3 H O
3-nonene ii) (CH3)2S
O H

CH3O OCH3 CH3O OCH3

i) O3
ii) (CH3)2S O O
H H O O

H H
 iv) Polymerization of alkenes
• Polymer: A large molecule composed of many smaller repeating units
(the monomers) bonded together.

• Alkenes serves as monomers for some of the most common polymers

such as polyethylene (polyethene), polypropylene, polystyrene,
poly(vinyl chloride) and etc.

• Undergo addition polymerization /chain-growth polymer:

- a polymer that results from the rapid addition of one molecule at a
time to a growing polymer chain, usually with a reactive intermediate
(cation, radical or anion) at the growing end of the chain.
repeating unit

CI H CI H CI H Cl H Cl
H CI H
C C C C C C C C C C C C
H H H H H H H H H H H H
n
vinyl chloride poly(vinyl chloride)
 SOME OF THE MOST IMPORTANT ADDITION POLYMERS

POLYMER POLYMER USES MONOMER POLYMER

FORMULA REPEATING UNIT
Polyethylene Bottles, bags,
films CH2 CH2 n
CH2=CH2

Polypropylene Plastics, olefin H CH3

fibers C C CH3
H H CH2 CH n

Polystyrene Plastics, foam

insulation H
C C H 2C C n
H H H

Poly(isobutylene) Specialized
H CH3
rubbers CH3
C C CH2 C n
H CH3 CH3
 Exercise 3.2
Predict the major product for the following reaction that is listed below.

a)
H2O2

b)

c)
d)

e)

f)

g)
Exercise 3.2- Answer
Exercise 3.2- Answer
Unsaturated
Tests of
Alkenes
i) Reactions of alkenes with
KMnO4
ii) Reactions of alkenes with
bromine.
UNSATURATION TESTS FOR ALKENES
i) Reaction of alkenes with KMnO4

- KMnO4 is a strong oxidizing agent.

- alkenes undergo oxidation reactions with KMnO4
solution under two conditions:
a) Mild oxidation conditions using cold, dilute,
alkaline KMnO4 (Baeyer’s test).
b) Vigorous oxidation conditions using hot,
acidified KMnO4.
a) Reaction of alkenes with cold, dilute, alkaline KMnO4 (Baeyer’s
test)
- the purple colour of KMnO4 solution disappears and a cloudy
brown colour appears caused by the precipitation of manganese
(IV) oxide, MnO2.
- test for carbon-carbon double or triple bonds.
- a diol is formed (containing two hydroxyl groups on adjacent
carbon atoms).
-
KMnO4 (aq), OH
C C C C MnO2
cold, dilute
OH OH
a diol
 ii) Reaction of alkenes with bromine
- A solution of bromine in inert solvent (CH2CI2 or CCI4) and dilute
bromine water are yellow in colour.
- The solution is decolorised when added to alkenes or organic
compounds containing C=C bonds.

CH2CI2
C C Br2 C C
Br Br

H 2O
C C Br2(aq) C C C C
OH Br Br Br
 DETERMINATION OF THE POSITION OF THE
DOUBLE BOND
a) Ozonolysis of alkenes:
- For example, ozonolysis of an alkene produces
methanal and propanone.
H CH3

H C O O C CH3
methanal propanone

remove the oxygen atoms from the carbonyl compounds and

joining the carbon atoms with a double bond.

H CH3 H CH3

H C C CH3 H C C CH3
2-methylpropene
b) Reaction of alkenes with hot, acidified KMnO4

- by using hot, acidified KMnO4, the diol obtained is

oxidised further.
- cleavage of carbon-carbon bonds occurs and the final
products are ketones, carboxylic acids or CO2.

CH3
KMnO4/H+ CH3
CH3 C CH2
CH3 C O CO2 + H2O
2-methylpropene
propanone
(ketone)
• Example:

An alkene with the molecular formula C6H12 is oxidised with hot

KMnO4 solution. The carboxylic acids, butanoic acid
(CH3CH2CH2COOH) and ethanoic acid (CH3COOH), are produced.
Identify the structural formula of the alkene.
i) cleavage of the double bond gives a mixture of carboxylic acids
H H +
KMnO4/H OH OH
R C C R'
R C O O C R'

ii) location of the double bond is done by taking away the oxygen atoms from the
carboxylic acids and then joining the carbon atoms by the double bond.
RCOOH and R'COOH RCH=CHR'

CH3CH2CH2COOH and CH3COOH CH3CH2CH2CH=CHCH3

butanoic acid ethanoic acid 2-hexene
REACTIONS OF ALKENES WITH HOT, ACIDIFIED
KMnO4
R R' R R'
KMnO4/H+
C C R'' C C H
R'' H OH OH

R R' R R'
C O O C C O
R'' R'' O C
OH H
ketone acid ketone aldehyde

+
KMnO4/H
R CH=CH2 R COOH + CO2 + H2O

Example:
+
KMnO4/H O HO
C C
O
4-methyl-4-octene 2-pentanone butanoic acid
Uses of
Alkenes
i) PE
ii) PVC
iii) ethanol
 USES OF ALKENES
• Ethylene and propylene are the largest-volume industrial organic
chemicals.
• Used to synthesis a wide variety of useful compounds.
H H
C C O O
oxidize
H H n CH3 C H CH3 C OH
polyethylene acetaldehyde acetic acid

polymerize
oxidize
O O2 H H Cl2 CH2 CH2
H 2C CH2 Ag catalyst C C
ethylene oxide H H CI CI
ethylene ethylene dichloride
H+ H2O NaOH
H2 O catalyst
CH2 CH2 CH3 CH2 H CI
OH OH OH H C C H
ethylene glycol ethanol vinyl chloride
i) POLYETHENE (PE)

• The most popular plastic.

• Uses:
i) Grocery bags
ii)Shampoo bottles
iii)Children's toy
iv)Bullet proof vests
v)Film wrapping
vi)Kitchenware
 ii) POLYVINYL CHLORIDE (PVC)
H H polymerize H CI H CI H CI
H C C CI C C C C C C
vinyl chloride H H H H n H H
poly(vinyl chloride)
PVC, "vinyl"
USES OF PVC:
❖ Clothing
- PVC fabric has a sheen to it and is waterproof.
- coats, shoes, jackets, aprons and bags.
❖ As the insulation on electric wires.
❖ Producing pipes for various municipal and industrial applications.
For examples, for drinking water distribution and wastewater
mains.
❖ As a composite for the production of accessories or housings for
portable electronics.
❖ used in the building industry as a low-maintenance material.
❖ Ceiling tiles.
 iii) ETHANOL
USE OF ETHANOL:
• Motor fuel and fuel additive.
• As a fuel to power Direct-ethanol fuel cells (DEFC) in order to produce
electricity.
• As fuel in bipropellant rocket vehicles.
• In alcoholic beverages.
• An important industrial ingredient and use as a base chemical for
other organic compounds include ethyl halides, ethyl esters, diethyl
ether, acetic acid, ethyl amines and to a lesser extent butadiene.
• Antiseptic use.
• An antidote.
• Ethanol is easily miscible in water and is a good solvent. Ethanol is less
polar than water and is used in perfumes, paints and tinctures.
• Ethanol is also used in design and sketch art markers.
• Ethanol is also found in certain kinds of deodorants.
OVERVIEW OF CHAPTER 3
 TUTORIAL 3
Question 1

Draw the correct structure of the compounds listed below.

a) 4,4-dimetyl-2-heptene
b) 7-bromo-1,3,5-cycloheptatriene
c) 2-phenyl-1,3-cyclopentadiene
d) 3,4-dibromo-1-butene
e) 2,3-dimethylcyclopentene

Question 2

Between 2-hexene and 3-hexene, choose only one alkene that should be
used to synthesize 3-bromohexane. Briefly explain why that alkene is chosen.
Question 3
Question 4

Predict the major products of compound C, D, E and F.

Question 5

Identify compound A, B, C, D and E to complete the reaction scheme below.

6)

7)