UNSATURATED

HIDROCARBONS

Unsaturated hidrocarbons contains

carbon-carbon double bonds.
Alkene

= olefin
Alkyne = acetylene
Aromatic compound = benzene ring

ALKENE

Alkena disebut juga olefin

Unsaturated hidrocarbon
Double bond
Pembentuk minyak
Rumus: CnH2n

Sifat

BM alkena < BM alkana

Titik didih alkena < alkana
Berat jenis alkena < air
Tidak larut dalam air & larut dalam
pelarut organik
Alkena lebih reaktif daripada alkana
Produksi alkena menghasilkan
alkana & alkohol

Nomenclature
(1)
1.

2.

Select the longest carbon-carbon chain

that cantains the double bond.
Name the parent compound as you
would an alkene but change the ane
ending to ene; for example, propane is
change to propene.
CH3 CH2 CH3
CH3CH=CH2
Propane

Propene

Nomenclature
(2)

3. Number the carbon chain of the parent

compound starting with the end nearer
to the double bond. Use the smaller of
the two numbers on the double-bonded
carbon atoms to indicate the position of
the double bond. Place this number in
front of the alkene name; for example,
2-butene means that the carbon-carbon
double bond is between carbon numbers
2 and 3.

Nomenclature
(3)

4. Side chains and other groups are

treated as in naming alkanes, by
numbering and assigning them to
the carbon atom to which they are
bonded.
College Chemistry_ch.22.2_p.551

Practice 1 :
Write structural formulas of :
1. 2-pentene
2. 7-methyl-2-octene
3. 3-hexene
4. 4-ethyl-2-heptene
5. 3,4-dimethyl-2-pentene

Geometric Isomerism in Alkenes

(1)

Geometric isomer
= isomer that differ from each other
only in the geometry of the
molecules and not in the order of
their atoms.

Geometric Isomerism in Alkenes

(2)

Geometric isomers are also called cis-trans isomers.

If the two chlorine atoms are locked on opposite sides of
the double bond, it is known as the trans isomer.
(trans : from latin meaning "across" - as in transatlantic).

If the two chlorine atoms are locked on the same side of

the double bond, it is known as the cis isomer.
(cis : from latin meaning "on this side")

Geometric Isomerism in Alkenes

(3)

Practise 2
Draw structural formulas and names
for all the isomers of pentene, C5H10.
Identify all geometric isomers.
Identify which one that have cis-trans
isomers, and draw the cis-trans
isomers.

Cycloalkenes
A cycloalkene or cycloolefin is a type of
alkene hydrocarbon which contains a
closed ring of carbon atoms, but has no
aromatic character.

cyclopropene cyclobutene

cyclopentene

cycloheptene

Preparation of Alkenes
Cracking/Pyrolisis
Adalah pemanasan hidrokarbon jenuh pada
suhu yang sangat tinggi dan dengan
bantuan katalis silika-alumina
Contoh:

C16H34
C8H18 + C8H16
alkane

alkane

alkene

Dehydration of Alcohols
Alkohol dipanaskan pada asam sulfat
terkonsentrasi
Reaksi:
Alkohol con.H2SO4
alkena + H2O

Contoh:

C C C C +H2SO4
OH
C C = C C +H2O
C C C = C +H2O

Alkenes Physical Properties

The first three alkenes are gases, the intermediate alkenes are liquids and
higher members of the olefin series are wax like solids at room temperature.
The alkenes are insoluble in water, but are soluble in organic solvents. The
liquids and solids have a density less than water.
Compound

Formula

MP
oC

BP
oC

Density
(g/ml)

Ethylene

C2H4
C3H6
C4H8

-170

-102

0.6128

-185

-47

0.6142

-130

-6.5

0.6356

Propene
Butene

Chemical Properties of Alkenes

(1)

Combustion of Alkenes
The alkenes are highly flammable and burn
readily in air, forming carbon dioxide and water.
C2H4 + 3 O2 2 CO2 + 2 H2O

Chemical Properties of Alkenes

(2)

Addition:
Addition of Hydrogen (hidrogenation)
Addition of Halogen (halogenation)
Addition of Hydrogen Halide
Addition of Water

Chemical Properties of Alkenes

(3)

Addition Reactions across the Double

Bond (oxidation)
3 H2C=CH2 + 2 KMnO4 + 4 H2O
2MnO2 + 2KOH + CH2OHCH2OH
Ethylene Glycol
During the oxidation of alkenes, the purple
colour of the permanganate solution
disappears and the reaction constitutes a test,
known as Baeyer's Test, to detect unsaturation
in any compound.

Chemical Properties of Alkenes

(4)

Reaction with Sulphuric Acid

Similarly, fuming sulphuric acid absorbs ethylene at
room temperature to form ethyl hydrogen sulphate, with
much evolution of heat.
C2H4 + H2SO4 C2H5.HSO4
If this is treated with water and warmed, ethanol is
formed.
heat

C2H5.HSO4 + H2O C2H5OH + H2SO4

Chemical Properties of Alkenes

(5)

Polymerisation Reactions due to the Double Bond

When ethylene is heated under great pressure in the presence of
a catalyst a large number of the molecules combine to form
polythene, (C2H4)n, (i.e. Polyethylene). This particular kind of
reaction is called an addition polymerisation and the mechanism
by which it takes place is a reaction is a free radical chain reaction.
The overall reaction is
n(C2H4) (C2H4)n
Ethene Polythene

Alkynes/Acetylene

Sifat:

Sifat hampir sama dengan alkena

Berupa gas tidak berwarna
Tidak larut dalam air & gas
pada tekanan & suhu normal
Sangat mudah terdekomposisi
Sebagai asetilen cair, bersifat
sangat sensitif dan dapat meledak.

Nomenclature
The procedure for naming alkynes is
the same as that for alkenes, but
the ending used is yne to indicate
the presence of a triple bond.

The name of some common alkynes :

_________________________________________________

Molecular
Formula

Structural
formula

Common
name

IUPAC
name

_________________________________________________

C2H2
C3H4
C4H6
C4H6

H-CC-H
CH3-CC-H
CH3CH2-CC-H
CH3-CC-CH3

Acetylene
Ethyne
Methylacetylene
Propyne
Ethylacetylene
1-Butyne
Dimethylacetylene2-Butyne

Prepraration

From calcium carbide and water

CaC2 + 2 H2O HCCH + Ca(OH)2

From cracking mathane

2 CH4 HCCH + 3 H2

Chemical Properties

Hidrogenation
Halogenation
Hidrogen halida

Aromatic Hydrocarbon

Structure
Aromatic compounds

benzene
C6H6

Naming :
Monosubstitued Benzenes
Monosubstitued benzenes are named by
adding the name of the substituent
group as a prefix to the word benzene.
Examples :

Nitrobenzene

Ethylbenzene

Chlorobenzene

Bromobenzene

Certain monosubstitued benzenes have

special names.
Methylbenzene = Toluene
Hydroxybenzene = Phenol
Vinylbenzene =Styrene
Benzene carboxylic acid = Benzenic acid
Benzene carboxaldehyd = Benzaldehyde
Aminobenzene =Aniline

Toluene

Phenol

Styrene

Benzoic acid

Benzaldehyde

Aniline

C6H6 group is known as phenyl/venil

The name phenyl is used to name compounds that
cannot easily be named as benzene derivatives.
Example :

Naming :
Disubstitued Benzenes
Names monosubstitued benzene
Except dimethylbenzene have special
name xylene.

Ortho, meta, and para substitution

Ketentuan
Ortho / para :
(dari yang paling kuat)
NH2

Meta :
(dari yang paling kuat)
NO2

OR
OH

CN
SO3H

OCOR
R
X

CHO
COR
COOH
COOR

Naming :
Polysubstitued Benzenes

When there are more than two

substituents on a benzene ring, the
carbon atoms in the ring are
numbered starting at one of the
substituted groups.

Polycyclic Aromatic Compounds

Chemical Properties

Halogenation (chlorination/bromination)
Nitration
Alkylation (Friedel-Crafts reaction)
Oxidation of side chain