Hydrocarbon

The Alkanes Fractional distilation of crude oil

condenser
- General formula of alkane is CnH2n+2 gas
- All C-C bond are single bond, it is called
pump gas separator
'saturated hydrocarbon' reflux
- Alkanes are non polar molecules, they dissolves gasoline
reflux from and
in organic solvent but not in water. kerosene
naphtha
fraction
- Melting and boiling point increase with kerosene
increasing in number of carbon atom. reflux from light
- Source of alkanes is crude oil, crude oil contain gas oil fraction

alkanes, cycloalkanes and arenes light gas oil

reflux from heavy

gas oil fraction
Cycloalkane is saturated hydrocarbon with a ring of 3
heavy gas oil
or more C-C bond, with general formula is like
alkene, CnH2n.

Reaction of Alkanes crude oil

residue
1. Combustion reaction
> complete combustion pump

heat steam
Alkane + O2 CO2 + H2O
ex :
- formation of toxic gas (carbon monoxide)
octane + oxygen carbon dioxide + water
2C8H18 + 25O2 16CO2 + 18H2O One of the problem of CO is can bind with haemoglobin,
making shortness of breath. Another problems are : dull
headeache, dizziness, confussion, blured vision and loss
>incomplete combustion of consciousness.

Alkane + O2 CO + H2O CO and NOx can be removed from exhaust gas by catalytic
converter. The catalyst is one of Pt/Pd/Rh metal. the reaction
or that happens in catalytic converter are :
Alkane + O2 C + H2O 2CO + 2NO 2CO2 + N2
ex : 2CO + 2NO 2 2CO2 + N2
2C8H18 + 17O2 16CO + 18H2O
unburn hydrocarbon + O2 CO2 + H2O
2C8H18 + 9O2 16C + 18H2O
- enhanced global warming
problem of combustion of alkane as a fuel in car engine the increase in average temperature around the world as the
consequence of the huge increase in the amount of CO2 and
- formation of nitrogen oxide other greenhouses gases produced by human activity.
N2(g) + O2(g) 2NO(g)
2NO(g) + O2(g) 2NO2(g)
2. Free radical substitution > Termination
UV light Whenever two free radicals meet they will react with
h
Alkane + X2 Halogenoalkane + HX
each other. A single molecule is the only product.
Steps of free radical substitution : As no free radicals are made that can carry on the
reaction sequence, the chain reaction stops.
> Initiation
CH3 + Cl CH3Cl
formation of free radical in UV light by
CH3 + CH3 C2H6
homolytic fission
UV light
X2 2X ■ In the initiation step we start with a molecule and get two
free radicals formed.
ex: ■ In the propagation steps we start with a molecule plus a
UV light
free radical and get a different molecule and a different
Cl2 2Cl free radical formed.
■ In the termination steps we start with two free radicals
and end up with a molecule and no free radicals.
> Propagation
Free radicals are very reactive. They will 3. Cracking
attack the normally unreactive alkanes. A
Condition for cracking :
chlorine free radical will attack the alkane
> thermal cracking, need high pressure and high
molecule:
temperature
CH4 + Cl CH3 + HCl > catalytic cracking, need high temperature and
catalyst (Al2O3 or SiO2)
CH3 + Cl2 CH3Cl + Cl
CH3Cl + Cl CH2Cl + HCl Large alkane shorter alkane + alkene
Large alkane alkene + H2
CH2Cl + Cl2 CH2Cl2 + Cl
ex:
In this mechanism the substitution reaction progresses
(grows) in a kind of chain reaction. C10H22 C4H10 + 2C3H6
This reaction is not really suitable for preparing
specific halogenoalkanes.

The Alkenes > Addition of hydrogen, H2(g)

- General formula of alkene is CnH2n Reagent : H2(g) + Ni catalyst
condition : heat at 140 oC
- Alkenes contain one or more C=C, it is called
'unsaturated hydrocarbon' Ni catalyst
Alkene + H2 Alkane
- Alkenes are non polar molecules, they dissolves ex :
in organic solvent but not in water. Ni catalyst
CH2 CH2 + H2 CH3CH3
ethene ethane
- Melting and boiling point increase with
increasing in number of carbon atom.
The mechanism of reaction :

- Source of alkenes are cracking of alkane.

Reaction of Alkanes intermediate

1. Electrophilic addition

In these reactions one of the two bonds in the carbon–

carbon double bond is broken and a new single bond is
formed from each of the two carbon atoms.
 > Addition of halogen (X2) > Addition of hydrogen halide, HX(aq)
Reagent : X2 Reagent : concentrated HX(aq)
condition : in the dark (no UV light) condition : rtp

Alkene + X2 Halogenoalkane Alkene + HX Halogenoalkane

ex: ex:
H H H H
CH2 CH2 + HBr CH3CH2Br
C C + Br2 ⎯
⎯→ H C C H
ethene bromoethane
H H Br Br
With longer, asymmetric alkenes there are always two
possible products that could be formed. For example, with
The mechanism reaction :
propene:
CH3CH CH2 + HBr CH3CH2CH2Br (minor product)
propene 1-bromopropane

and
CH3CH CH2 + HBr CH3CHBrCH3 (major product)
propene 2-bromopropane

The mechanism reaction :

> Addition of steam, H2O(g)
Reagent : H2O(g) + H3PO4/H2SO4 catalyst
secondary carbocation (more stable)
condition : heat at 330 oC + 6Mpa

Alkene + H2O(g) ⎯
⎯→ Alcohol
ex: (major product)

H H H OH
H3PO4
C C + H2O H C C H
H H (primary carbocation
H H (less stable)
(minor product)

2. Oxidation Reaction
> Strong Oxidation / Oxidation cleavage
> Mild Oxidation
Reagent : concentrated acidified KMnO4 (conc. MnO4-, H+)
Reagent : acidified KMnO4 (MnO4-, H+)
condition : heat / hot
condition : cold + dilute
1 H
Alkene + H2O + [O] Diol C C CO2 + ...
ex : H carbon dioxide
2 R R
H H OH OH
C C C O + ...
C C + O + [O] H C C H
H H
H H H H H H an aldehyde
ethene ethane-1,2-diol further oxidation
O
R C

OH
a carboxylic acid
3 R1 R1
C C C O + ...
2 2
R R
 ex:

1.
2.

hot conc. manganate(VII) ion, H+

3.

3. Addition polymerisation

Formation of large molecule (polymer) from

many small reactive molecule (monomers).
It involves the breaking of the π bond in each
C=C bond, then the monomers link together.
Condition : high pressure + high temperature

Alkenes polyalkene

ex :

1. nC2H4 –C
[ 2H4 ] n –
ethene poly(ethene)

or by using the displayed formulae:

H H H H
n C C C C
H H H H n
n is very large, e.g. up to 10 000

—CHCl
2. nH2C— [ 2C—CHCl–
–H ]n
chloroethene poly(chloroethene)
or poly vinyl chloride (PVC)