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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
isobutane
CH3(CH2)2CH3 CH3CH(CH3)2
C5H12
IUPAC NOMENCLATURE
CH3CH2CH2CH2CHCH3
|
CH3
CH2
CH3
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
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.
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.
General formula:
CnH2n where n = 3, 4, 5, ……
NOMENCLATURE OF
CYCLOALKANES
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