CLD 10302

ORGANIC CHEMISTRY
CHP2 : HYDROCARBON
Prepared By:
ARBANAH MUHAMMAD

TOPICS COVERED
2.1 Introduction in Process Industry
2.2 Natural Gas and Petroleum Resources
2.3 Alkanes
2.4 Alkenes, Addition Polymerization and
The Chemistry of Rubber
2.5 Alkynes
2.6 Chlorinated Alkanes and Geometrical
Isomers
2.7 Aromatic Hydrocarbon

2.1 Introduction in Process Industry

Petroleum Refining
Polyolefins
Olefins
Ammonia and Urea

2.2 Natural Gas and Petroleum Resources

Gas Processing Plant

Introduction
Classification of Hydrocarbon

Hydrocarbon
Aromatic

Aliphatic
Alkanes

Alkenes

Alkynes

CycloalkanesCycloalkenes

Saturated

Unsaturated

Alkane
1.
2.
3.
4.
5.
6.
7.

Alkanes
Alkanes Nomenclature System
Structural Isomers
Cycloalkanes
Sources of Alkanes and Cycloalkanes
Synthesis of Alkanes
Reaction of Alkanes

1. Alkane
Simplest member of
hydrocarbon family
Cn H 2 n 2
General formula:
H
Contains only C H
Saturated compound
Alkanes are hydrocarbons in
which all of the bonds are
single bonds
Alkanes whose carbon
atoms are joined in rings are
called cycloalkanes.

Ethane

No
of C

Molecul
ar
Formul
a

Condens
ed
Formula

Structural
Formula

Bond Line
Formula

Boiling Point
Melting
Point
(C)

C1H4

-182.5 -161.6

C2H6

-183.3

-88.6

C3H8

-189.7

-42.1

C4H10

-138.7

-0.5

C5H12

-129.8

36.1

C6H18

-95.3

68.7

C7H16

-90.6

98.4

C8H18

-56.8

125.7

C9H20

-53.5

150.8

10

C10H22

-29.7

174.0

Substituent: Alkyl Groups

Alkyl group is a group which is
derived from unbranched-chain
alkanes by removing 1 H atom
from the end C atom
General formula : CnH2n + 1
Represented by R symbol
suffix : - yl

e.g: eth-yl

Substituent: Alkyl Groups

No of
C

Name

Structure

Methyl

- CH3

Ethyl

-CH2CH3

Propyl

-CH2CH2CH3

Isopropyl

Butyl

CH3 CH - CH3

-CH2CH2CH2CH3

Sec-butyl
H

No of
C
4

Name

Structure

Iso-butyl

CH3 H

CH3 H

Tert-butyl
H

Pentyl

C H
H

CH3(CH2)4CH2-

Iso-pentyl
H

Neo-pentyl
H

CH3 H

CH3 H

CH3 H

2. Alkanes Nomenclature System

Step 1) Find the longest continuous carbon chain
and use the IUPAC name of the unbranched
alkane as the basis.
Step 2) Add name of substituent as a prefix. Use
base name with yl ending. Use replicating
prefixes (di-, tri-, tetra-, etc.) according to the
number of substituents attached to the main
chain.
Step 3) Number the chain from the end nearest
the substituent, and identify the carbon to
which the substituent is attached by number.
Step 4) List substituents in alphabetical order.

Base Name - sufix

Alkane

The proper suffix is

determined by :
i.

ii.

CH2

- methane

C2H6

-ethane

functional groups

C3H8

-propane

present

C4H10

-butane

C5H12

-pentane

C6H14

-hexane

C7H16

-heptane

C8H18

-octane

C9H20

- nonane

C10H22

- decane

identifying all the

Polyfunctional organic
compounds contain
many different kinds
of functional groups.
Then choose the
principal group of
highest priority

Practice
Exercis

Give IUPAC name for the following compound

Example

H 3C

H
C

H
C

CH3

CH3 CH3
2,3-dimethylbutane

Case 2

When 2 or more of different kind of

substituents present :

the substituents are listed alphabetically

prefixes di, tri, tert are ignored
in
1

alphabetising
2

CH
CH
3
neo
methyl

CH3

CH2

except
iso and
5

CH

CH2
CH3

4-ethyl-2-methyl.

CH2

ethyl

CH3

Practice
Exercis

Give IUPAC name for the following compound

Example

CH3
H3C

C
CH3

CH2

CH

CH2

CH2
CH3

4-ethyl-2,2-dimethylhexane

CH3

Practice
Exercis
e

CH3

H3C

CH2

CH2

CH

CH3

5 CH

CH3

CH3

Continuous C
chain :
Prefix

6C
hex
:

Suffix

:- ane

Substituent

: dimethyl & ethyl

4-ethyl-2,2-dimethylhexane

Case 3
When 2 chains of equal length compete for
selection as parent chain, choose the chain with
the greater number of substituents

CH3
H3C

CH2

CH

CH
CH2

Example

CH2

CH3

CH3

CH

CH

CH3

2,3,5-trimethyl-4-propylheptane
(4 substituents)

CH3
CH3
H3C

CH2

CH

CH
CH2

4-sec-butyl-2,3-dimethylheptane
(3 substituents)

CH2
CH3

CH3

CH3

CH

CH

CH3

Practice
Exercis

Give IUPAC name for the following compound

Example

CH3
H3C

CH2CH3
CH2

CH2

CH CH3

CH3

5-ethyl-2,2-dimethylheptane

Case 4

When first branching occurs at an equal distance

from either end of the longest chain, choose the
name that gives the lower number at the first
point of different

CH3
5
6
H3C
CH

CH2 3CH

CH

1CH

CH3

CH3

2,3,5trimethylhexane

Example

CH3
1

H3C

CH

CH3

CH2

CH

5CH

6CH

CH3

2,4,5trimethylhexane

Practice
Exercis

Give IUPAC name for the following compound

CH3

1 2
H3C C

CH2CH3

CH2

CH2

CH CH3

CH3
Continuous C
chain :
Prefix

hept
:

Suffix

:- ane

Substituent

: trimethyl

Locant

7C

: 2, 2, 5

2,2,5-trimethylheptane

Structural Isomers Alkane

Compounds with same number of
atom and bonds but different
arrangement

C4H10

H3C

H2
C

C
H2

butane

CH3

CH3

H
C CH3

CH3
2-methylpropane

Number of Constitutionally
Isomeric Alkanes
CH4 1

C8H18

18

C2H6 1

C9H20

35

C3H8 1

C10H22 75

C4H10

C15H32 4,347

C5H12

C20H42 366,319

C6H14

C40H82 62,491,178,805,831

C7H16

Number of isomeric alkanes

increases as the number of
carbons increase.
There is no simple way to
predict
how many isomers there are
for a

Cycloalkanes

Cyclic alkane with general formula:

CnH2n
Parent name: alkane . Add cylco in
front.
Cyclopropa
ne
cyclobutane

cyclopentan
e

cyclohexane

If only one substituent present :

Case 1not necessary to

designate its position

Exam
ple

suffix

prefix

6C

CH3

cyclo
hex
ane
Methyl

Case 2
When 2 substituents present :
i.

Numbered the C beginning

with substituent according to
the alphabetical order

ii.

Numbered in the way that

gives the next substituent the
lowest number possible

Exam
ple 1

Methyl
3

-ethyl-2-methyl
cyclohexane4

1
5

CH2CH3
Ethyl

CH3
1

CH3

CH2CH3

1-ethyl-6-methylcyclohexa

Naming of Cycloalkane

CH2CH3

Ethylcyclopentane

H 3C CH3

3-Ethyl- 1,1-dimethylcyclohexane
CH2CH3

Practice
Exercise
Give
IUPAC names for the following
cycloalkanes :
CH3

H3C
CH3

H3 C

dimethylcyclohexane
Isopropylcyclobuta
CH2CH3

1-ethyl-3-methylcyclopenta
CH3

When single ring is attached to a chain with

Case 4

greater no. of C atoms :

named as

cycloalkylalkane

5 C chain

par
CH2 CH2 CH2 CH2 CH3 ent
3
4
5
1
2
4C
ch
ain
substi
tuent

1 cycbu pent
- lo tyl ane

When more than 1 ring is attached to a single

chain :

Case 5 also named as cycloalkylalkane

parent

straigh
t chain
CH
CH CH
1

22

23

substituent groups
1,3di
cyclo
hexyl
propane

Alkane
Physical Properties
Non polar molecules
Not soluble in water
Low density
Low melting point
Low boiling point

These goes up as the number

of carbons increase

Practice
Exercise
Arrange
the following compounds in order of
increasing boiling point
CH3CH2CH3
propane

CH3CH2CH2CH2CH3
n-pentane

CH3( CH2)7 CH3

n-nonane

Boiling point
increases

Sources of Alkanes and

Cycloalkanes

C55-C12
12
Naphtha
(bp 95-150 C)

Light gasoline
(bp: 25-95 C)

C12
-C15
12
15
Kerosene
(bp: 150-230 C)

Crude oil

C15
-C25
15
25

Gas oil
(bp: 230-340 C)

C11-C44
Refinery gas
Residue

Petroleum Refining
Cracking

converts high molecular weight hydrocarbons

to more useful, low molecular weight ones
i) thermal cracking (by heat)
ii) catalytic cracking (with the aid of catalyst)

Reforming

) increases branching of hydrocarbon chains

) branched hydrocarbons have better burning
characteristics for automobile engines

Hydrogenation
Hydrolysis
Reduction

Synthesis of Alkanes

Hydrogenation
General reaction : Addition
H

H
C

Pt / Pd / Ni

H2

H
alkene

hydrogen

Example:
Ni

C2H4 + H2 C2H6
ethene

ethane

alkane

Hydrolysis of Grignard
(alkylmagnesium halide)

reagent

H+

RMgX + H2O RH +
alkane
Mg(OH)X
alkylmagnesium
halide

Example:
H+

CH3CH2CH2MgCl + H2OCH3CH2CH3 + Mg(OH)Cl

Propylmagnesium
chloride

Propane

Wurtz reaction (Reduction of alkyl

halide)
2RX + Na R-R + 2NaX
alkyl halide

reducing
agent

alkane

Example:
2CH3CH2CH2Br + 2Na
bromopropane
CH3CH2CH2CH2CH2CH3hexane
+ 2NaBr

Reaction of alkanes

Combustion
Halogenation

Combustion
alkane O 2 CO 2 H 2 O

Usage:
Fuel

Halogenation
Light/heat

Usage:
Dichloromethane: Paint stripper
1,2 Dichloroethane: Dry cleaning fluid