BNQ10204

SEM I (2022/2023)

CHAPTER 3: HYDROCARBONS

PREPARED BY: DR NADIRUL HASRAF MAT NAYAN

REVISED & DELIVERED BY: ASSOC. PROF. DR NOOR AKHMAZILLAH MOHD FAUZI

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 OUTLINE

3.0 Introduction to Hydrocarbons

3.1 Alkanes
3.2 Alkenes and Alkynes
3.3 Aromatic Hydrocarbons
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 3.0 Introduction to Hydrocarbons

What are Hydrocarbon?

 HYDROCARBONS are the compounds
containing carbon and hydrogen only
 Depending upon the types of carbon-carbon
bonds present, they can be classified into
tree main categories:
1) Saturated Hydrocarbon
2) Unsaturated Hydrocarbon
3) Aromatic Hydrocarbon
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 3.0 Introduction to Hydrocarbons:
Saturated Hydrocarbon

• These include open chain hydrocarbon as well as closed

chain hydrocarbons.
• These compounds are called SATURATED because they
have maximum number of bonded hydrogen
• If different carbon atoms are joined together to form an
open chain of carbon atoms with single bonds, they are
called Alkanes. For example: 2-Methylpropane (Isobutane)
• If carbon atoms form a closed chain or ring, they are
called Cycloalkanes. For example: Cyclopentane

The hydrocarbon that contain only carbon-carbon

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single bond is called Saturated Hydrocarbon
 3.0 Introduction to Hydrocarbons:
Unsaturated Hydrocarbon

The hydrocarbons which contain carbon-carbon multiple bond (Double

bonds or triple bond) are called unsaturated hydrocarbon.
Depending upon multiple bond they are further classified as alkenes and
alkynes
Alkenes : These are hydrocarbon which contain at
least one carbon-carbon bond. For example: Ethene

Alkynes: These are hydrocarbons which contain at

least one carbon-carbon triple bond. For example:
Ethylene 5
 3.0 Introduction to Hydrocarbons:
Aromatic Hydrocarbon

The hydrocarbons which contain at least one special type of hexagonal

ring of carbon atoms with three double bond in the alternate positions are
called aromatic hydrocarbon. The ring is called aromatic ring.
For example: i) Toluene ii) o-Xylene

The aromatic compounds may also contain more than one benzene rings.
For example: i) Naphthalene ii) Anthracene
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 3.1 Alkanes

Alkanes are saturated hydrocarbon containing only carbon carbon single

bond in their molecule. They are also called Paraffins. At high temperatures
and pressure do undergo some reaction. The alkanes may be divided as:

1) Open chain or Acyclic alkanes .

These are simple alkanes without any close chains and
have the general formula where CnH2n + 2 . Where n is the
number of carbon atoms. For example: i) Methane - CH4

2) Cycloalkanes or cyclic alkanes. i)Cyclopropane

These contain a closed chain or ring in their
molecules. They have the general formula CnH2n.
ii)Cyclobutane
 3.1 Alkanes: Structure of Alkanes

Methane is the first member of the

family. It has Tetrahedral Structure
involving sp3 Hybridisation. The four
sigma bond is formed by the
overlapping of sp3 hybrid orbitals of
carbon and 1s orbital of hydrogen. In
this, carbon atom lies at the centre and
the four hydrogen atoms lies at the
corners of a regular tetrahedron.
Making H-C-H bond angle of 109.5˚
 3.1 Alkanes: Preparation of Alkanes

Petroleum and natural gas are the main source of alkanes. However, alkanes can be
prepared by three methods
 The hydrogenation reaction of
unsaturated hydrocarbon using nickle at
a tempreture of 523-573K is commonly
known as Sabatier and Sender’s reaction
or reduction This process of
elimination of carbon
dioxide from a carboxylic
acid is known as
decarboxylation.
Sodium salts of carboxylic
acids on heating with soda
lime (mixture of sodium
hydroxide and calcium
oxide)gives alkanes
containing one carbon atom
less than the carboxylic acid

The unsaturated hydrocarbons (alkenes and alkynes)

are converted into alkanes by CATALYTIC
HYDROGENATION. In this process dihydrogen is passed
through alkenes or alkynes in the presence of finely An aqueous solution of sodium or
divided catalysts such as Raney Ni, Pt or Pd. These potassium salt of a carboxylic acid on
metals absorb dihydrogen gas on their surfaces and electrolysis gives alkane containing even
activate the hydrogen-hydrogen bond. Platinum and number of carbon atoms at the anode.
palladium catalyse the reaction at room tempreture.
However,higher tempreture (523-573k) and pressure
are required with nickle catalysts
 3.2 Alkenes and Alkynes

Alkenes
Alkenes are unsaturated hydrocarbons containing
carbon carbon double bond (C═C)in their
molecules. They have the general formula CnH2n .
The simplest member of alkene family is ethene,
C2H4 . The alkenes are also called olefins (Greek
olefiant meaning oil forming) because the larger
member of the series (such as ethylene,
propylene, etc react with chlorine to form oily
products.
Alkynes
Alkynes are unsaturated hydrocarbon having
carbon carbon triple bonds in their molecules.
There general formula is CnH2n-2 . The simplest
member of this class is ethyne (C2H2 ) which is
properly known on acetylene.

Propylene
Alkynes can be reduced to alkenes using palladium charcoal (palladised
charcoal) catalyst partially deactivated with poison like sulphur compounds or
quioline. Partially deactivated palladised charcoal is known as Lindlar’s catalyst.
Alkynes can also be reduced to alkenes with sodium in liquid ammonia (called
BIRCH REDUCTION).

Nature of halogen atom and the

alkyl group determine rate of the
reaction. It is observed that for
halogens, the rate is:
Iodine>Bromine>Chlorine while for
alkyl group it is Tertiary>
Secondary>Primary
Alkene can be prepared from alkyl halides(usually bromides or iodides) by
treating with alcoholic potash(potassium hydroxide dissolved in ethanol). This
reaction removes a molecule of HX and therefore, the reaction is called
DEHYDROHALOGENATION. In this reaction, the hydrogen atom is eliminated
from β carbon atom (carbon atom next to the carbon to which halogen is
attached). Therefore, the reaction is also called β–elimination reaction.

Dihalogen derivatives of alkanes in which two halogens atoms are attached to adjacent carbon
atoms (called vicinal dihalogen derivatives) are converted to alkenes by heating with zinc dust in
ethyl alcohol.
For eg: CH3CHBr−CH2Br+Zn CH3CH=CH2+ZnBr

Alkenes are prepared from alcohols by heating with protonic acids such as sulphuric acid at
about 443K. This reaction is called dehydration of alcohols.
For eg: CH H2SO4 or H3PO4 3CH2OH CH2=CH2+H2O
This reaction is also an example of β-elimination reaction
because –OH group takes out one hydrogen atom from the
β- carbon atom.
Vicinal dihalides on treatment with alcoholic
potassium hydroxide undergo
dehydrohalogenation. One molecule of
hydrogen halides is eliminated to form
alkenyl halide which on treatment with
sodamide gives alkyne.

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 3.5 Aromatic Hydrocarbons

These hydrocarbons are also known as ‘arenes’. Since most of them possess
pleasant ODOUR (Greek; aroma means pleasant smelling), the class of
compounds was named as ‘aromatic compounds’. The parent member of
the family is benzene having the molecular formula C6H6. it has hexagonal
ring of six carbon atoms with three double bond in alternate position.
AROMATICITY
o Aromatic compounds are those which resembles benzene in
chemical behaviour.
o These compounds contain alternate double and single bonds in a
cyclic structure.
o They undergo substitution reaction rather than addition reaction.
o This characteristic behaviour is called aromaticity.
o The aromaticity depends upon the electronic structure of the
molecule.

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Preparation of Benzene
➢ Decarboxylation of aromatic acid Benzene is prepared in the laboratory by heating
sodium benzoate with soda lime.

➢ Reduction of phenol Benzene can be prepared from phenol by distillation with zinc.

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End of Chapter

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