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Chapter 13.

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HYDROCARBONS
13.1 : ALKANES

Hydrocarbon
are compounds which
contain only carbon and
hydrogen atoms.
HIDROCARBONS

AROMATIC
ALIPHATIC
(contain one or more benzene ring)

ALKANES ALKENES
(saturated) (unsaturated) ALKYNES
contain only contain (unsaturated)
single bond C=C contain
C≡C

CYCLO-ALKANES (saturated) CYCLO-ALKENES


Alkanes which C atoms are (unsaturated)
join in rings
• Saturated hydrocarbons
- compound with C-C
- Example : alkanes and cycloalkanes

– Contain the maximum number of


hydrogen atoms that the carbon
compound can possess.
• Unsaturated hydrocarbons
-compounds with multiple bonds
-Example : alkenes, cycloalkenes,
alkynes and aromatic hydrocarbons

– They posses fewer than the


maximum number of hydrogen
atoms.
ALKANES

Alkanes are known as saturated hydrocarbon which contain


only single covalent bonds.

General formula for straight chain of alkanes is CnH2n+2


where n ≥ 1
General formula for cycloalkanes is CnH2n
where n ≥ 3
 Each carbon atom in alkanes is
- sp3 hybridised
- tetrahedral with four sigma bond (formed by
the four sp3 hybrid orbitals.)
- all bond angles are close to 109.5o

 Alkanes IUPAC names have the –ane suffix.


The First Ten Unbranched Alkanes
Molecular Structural formula No .of C Name
formula atoms
CH4 CH4 1 Methane
C2H6 CH3—CH3 2 Ethane
C3H8 CH3—CH2—CH3 3 Propane
C4H10 CH3—(CH2)2—CH3 4 Butane
C5H12 CH3—(CH2)3—CH3 5 Pentane
C6H14 CH3—(CH2)4—CH3 6 Hexane
C7H16 CH3—(CH2)5—CH3 7 Heptane
C8H18 CH3—(CH2)6—CH3 8 Octane
C9H20 CH3—(CH2)7—CH3 9 Nonane
• Starting from C4H10 onwards, the alkanes
show the phenomenon of chain isomerism.

• They can exist as linear or branched alkanes.


Example
C4H10
2-

isobutane

CH3(CH2)2CH3 CH3CH(CH3)2
C5H12
IUPAC NOMENCLATURE

 IUPAC – International Union of Pure


and Applied Chemistry

 Branched - chain alkanes are named


according to the following rules:
Choose the longest continuous chain
of carbon atoms; this chain determines
the parent name for alkanes.
Examples:

CH3CH2CH2CH2CHCH3
|
CH3

Parent name: hexane


CH3CH2CH2CH2CHCH3

CH2
CH3

Parent name : heptane


Number the longest chain beginning
with the end of the chain nearer the
substituent.
Example:
6 5 4 3 2 1

CH3CH2CH2CH2CHCH3

CH3 substituent
7 6 5 4 3
CH3CH2CH2CH2CH CH substituent
3
|
2 CH2
|
1 CH3
Use rule number 2 to locate the position
of the substituent.


The position and the name of the
substituent must be written in front of
the parent chain.
Examples:
6 5 4 3 2 1

CH3CH2CH2CH2CHCH3
Substituent
CH3 -methyl at C-2

2-methylhexane
Substituent

7 6 5 4 3 -methyl at C-3
CH3CH2CH2CH2CH CH3
|
2 CH
2
|
1
CH3

3-methylheptane
Some Common Substituent Groups
Alkane name substituent

methane methyl CH3

ethane ethyl CH2CH3

propane propyl CH2CH2CH3


CHCH3
isopropyl
CH3
butane butyl CH2CH2CH2CH3
isobutyl CH2CHCH3

CH3
sec-butyl
CHCH2CH3

CH3
tert-butyl CH3
CCH3
CH3
neopentyl CH3
CH2CCH3
CH3
cyclopropyl

cyclobutyl

phenyl
−C6H5 or

benzyl
CH2
name substituent
Bromo -Br
Chloro -Cl
Flouro -F
Iodo -I
Hydroxyl -OH
Amino -NH2
Cyano -CN
Nitro -NO2
If two or more substituents are present,
give each substituent a number
corresponding to its location on the longest
chain.


the substituent should be listed
alphabetically.

 In alphabetizing, the prefixes di, tri, tetra,


sec-, tert- are ignored except iso and
neo.
Example:
1 2 3 4 5 6
CH3CHCH2CHCH2CH3
| |
CH3 CH2
|
CH3

4-ethyl-2-methylhexane
If two substituents are present on the
same carbon atom, use that number twice
Example:
CH3
|34 5 6
CH3CH2CCH2CH2CH3
|
2
CH2
|
1
CH3
3-ethyl-3-methylhexane
If two or more identical substituents are
present, use prefixes di-(2 identical
substituents),tri-(3 identical substituents),
tetra-(4 identical substituents).
Commas are used to separate numbers
from each other.

Example:
CH3CH―CH CH3 2,3-dimethylbutane
| |
CH3 CH3
If there are two chains of equal length as
the parent chain, choose the chain with
the greater number of substituents.
7 6 5 4 3 2 1
4 3 2 1
CH3CH2-CH CH CH CHCH3
| | | |
CH3 5 CH2 CH3 CH3
|
6
CH2
7
|
CH3
2,3,5-trimethyl-4-propylheptane
(four substituents)
4-sec-butyl-2,3-dimethylheptane
(three substituents)
If 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 difference.
6 5 4 3 2 1
CH3CHCH2CH CHCH3
1 2 3 4 5 6
| | |
CH3 CH3 CH3

2,3,5-trimethylhexane

(NOT 2,4,5-trimethylhexane)
CYCLOALKANES
Cycloalkanes – alkanes which carbon
atoms are joined in rings.

Cycloalkanes are known as saturated


hydrocarbon, because it has the
maximum number of bonded hydrogen
( only has single bonds).

General formula:
CnH2n where n = 3, 4, 5, ……
NOMENCLATURE OF
CYCLOALKANES

Cycloalkanes with only one ring are


named with the prefix cyclo- to the
names of the alkanes (contain the
same number of carbon atoms)
Examples: Monocyclic compounds

C3H6 cyclopropane

C4H8 cyclobutane

C5H10 cyclopentane
If only one substituent is present, it is not
necessary to designate its position.

Examples:

Chlorocyclopropane
Cl

CH3 Methylcyclohexane
If two substituents are present,
number carbon in the ring beginning
with the substituent according to the
alphabetical order
and
number in the direction that gives
the next substituent the lowest
number possible.
Examples:

CH3

3
2

4 CH2CH3
1

5 6

1-ethyl-2-methylcyclohexane
NOT
1-ethyl-6-methylcyclohexane
2
Cl 3 1
Cl

4 5

1,3-dichlorocyclopentane
(NOT 1,5-
dichlorocyclopentane)
When three or more substituents are
present, begin at the carbon with
substituent that leads to the lowest set of
locants.
Locants
Example:
CH2CH3 chloro 1 4
2 3

1
3 2
4 ethyl 3 2
Cl 4 1 CH3
methyl 4 1
5 6
6 5

1-chloro-3-ethyl-4-
methylcyclohexane

4- chloro-2-ethyl-1-
methylcyclohexane
H3C CH2CH3

CH3
1-ethyl-1,3-dimethylcyclopentane
(NOT 3-ethyl-1,3-dimethylcyclopentane)
When a single ring system is attached
to a single chain with a greater number
of carbon atoms
or
when more than one ring system is
attached to a single chain, then it is
appropriate to name the compounds as
cycloalkylalkane.
Number of C at
linear chain
Number of C at ring
1 3

1,3-dicyclohexylpropane
Examples:

CH2CH2CH2CH2CH3

1-cyclobutylpentane