Chapter 13.

0
HYDROCARBONS

are compounds which
contain only carbon and
hydrogen atoms.
13.1 : ALKANES
Hydrocarbon

ALKANES
(saturated)
contain only
single bond
ALKENES
(unsaturated)
contain
C=C
CYCLO-ALKANES (saturated)
Alkanes !ic! C ato"s are
#oin in rings
ALKYNES
(unsaturated)
contain
C$C
CYCLO-ALKENES
(unsaturated)
H%&'OCA'(ONS
A'O)A*%C
(contain one or "ore ben+ene ring)
AL%,HA*%C

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

hey posses fewer than the

maximum number of hydrogen
atoms.

ALKANES
Alkanes are known as saturated !ydrocarbon which contain
only single co-alent bonds.
eneral !ormula !or straight chain o! alkanes is C
n
H
.n/.

where n 0 1
eneral !ormula !or cycloalkanes is C
n
H
.n
where n 0 2

Each carbon atom in alkanes is

" sp
3
hybridised
" tetrahedral with !our sigma bond #!ormed by
the !our sp
3
hybrid orbitals.$
" all bond angles are close to 1%&.'
o

Alkanes ()*A+ names ha,e the -ane su!!i..

/he 0irst /en )nbranched Alkanes
1olecular
!ormula
Structural !ormula No .o! +
atoms
Name
+2
3
+2
3
1 1ethane
+
4
2
5
+2
3
6+2
3
4 Ethane
+
3
2
7
+2
3
6+2
4
6+2
3
3 *ropane
+
3
2
1%
+2
3
6#+2
4
$
4
6+2
3
3 8utane
+
'
2
14
+2
3
6#+2
4
$
3
6+2
3
' *entane
+
5
2
13
+2
3
6#+2
4
$
3
6+2
3
5 2e.ane
+
9
2
15
+2
3
6#+2
4
$
'
6+2
3
9 2eptane
+
7
2
17
+2
3
6#+2
4
$
5
6+2
3
7 :ctane
+
&
2
4%
+2
3
6#+2
4
$
9
6+2
3
& Nonane
+
1%
2
44
+2
3
6#+2
4
$
7
6+2
3
1% ;ecane


<
Starting !rom +
3
2
1%
onwards= the alkanes
show the phenomenon o! chain isomerism.
< /hey can e.ist as linear or branched alkanes.

Example
+
3
2
1%

+2
3
#+2
4
$
4
+2
3
+2
3
+2#+2
3
$
4
4"
isobutane

+
'
2
14

%3,AC NO)ENCLA*3'E
%3,AC NO)ENCLA*3'E

%3,AC 4 %nternational 3nion o5 ,ure

and A66lied C!e"istry

(ranc!ed - c!ain alkanes are na"ed

according to t!e 5olloing rules7

C!oose t!e longest continuous c!ain
o5 carbon ato"s8 t!is c!ain deter"ines
t!e 6arent na"e 5or alkanes9
E.amples:
CH
2
CH
.
CH
.
CH
.
CHCH
2
>
+2
3
,arent na"e7 !e:ane

CH
2
CH
.
CH
.
CH
.
CHCH
2
CH
.
CH
2
,arent na"e 7 !e6tane

Nu"ber t!e longest c!ain beginning
Nu"ber t!e longest c!ain beginning
it! t!e
it! t!e
end o5 t!e c!ain nearer t!e
end o5 t!e c!ain nearer t!e
substituent9
substituent9
CH
2
CH
.
CH
.
CH
.
CHCH
2
E.ample:
CH
2
substituent
1 ;
<
. 2 =

CH
2
CH
.
CH
.
CH
.
CH
>


CH
.
>


CH
2
substituent
CH
2

1
4
3 3 ' 5
9

3se rule nu"ber . to locate t!e 6osition
o5 t!e substituent9

*!e 6osition and t!e na"e o5 t!e

substituent "ust be ritten in 5ront o5
t!e 6arent c!ain9

CH
2
CH
.
CH
.
CH
.
CHCH
2
E.amples:
CH
2
.-"et!yl!e:ane
1 ;
<
. 2 =
Substituent
"methyl at +"4

CH
2
CH
.
CH
.
CH
.
CH +2
3

>


CH
.
>


CH
2
2-"et!yl!e6tane
1
.
2 < = ; ?
Substituent
"methyl at +"3

butyl
isopropyl
propyl
ethyl
methyl
substituent name
+2
3
+2
4
+2
3
+2
4
+2
4
+2
3
+2+2
3
+2
3
+2
4
+2
4
+2
4
+2
3

So"e Co""on Substituent @rou6s
So"e Co""on Substituent @rou6s

Alkane
methane
propane
butane
ethane

isobutyl
sec"butyl
tert"butyl
neopentyl
+2
4
+2+2
3
+2
3
+2+2
4
+2
3
+2
3
+2
3
+2
3
++2
3
+2
3
+2
4
++2
3
+2
3

cyclopropyl
cyclobutyl
phenyl
ben?yl
C
6
H
5
or
+2
4

name substituent
8romo "8r
+hloro "+l
0louro "0
(odo "(
2ydro.yl ":2
Amino "N2
4
+yano "+N
Nitro "N:
4

(!
(!
two or more substituents are present
two or more substituents are present
=
=
gi,e each substituent a number
gi,e each substituent a number
corresponding to its location on the longest
corresponding to its location on the longest
chain.
chain.

the substituent should be listed

the substituent should be listed
alphabetically
alphabetically
.
.

(n alphabeti?ing= the pre!i.es

(n alphabeti?ing= the pre!i.es
di= tri= tetra=
di= tri= tetra=
sec"= tert" are ignored
sec"= tert" are ignored
e.cept
e.cept
iso and
iso and
neo
neo
.
.

E.ample:

1 4 3 3 ' 5
+2
3
+2+2
4
+2+2
4
+2
3

> >
+2
3
+2
4
>
+2
3

3"ethyl"4"methylhe.ane

(!
(!
two substituents
two substituents
are present on the
are present on the
same carbon atom=
same carbon atom=
use that number twice
use that number twice
E.ample:
+2
3
>
33 ' 5
+2
3
+2
4
++2
4
+2
4
+2
3
>

4
+2
4
>

1
+2
3
3"ethyl"3"methylhe.ane

(!
(!
two or more identical substituents
two or more identical substituents
are
are
present= use
present= use
pre!i.es di"#4 identical
pre!i.es di"#4 identical
substituents$=tri"#3 identical substituents$=
substituents$=tri"#3 identical substituents$=
tetra"#3 identical substituents$.
tetra"#3 identical substituents$.


+omma
+omma
s are used to separate numbers
s are used to separate numbers
!rom each other.
!rom each other.
E.ample:
E.ample:
+2
+2
3 3
+2
+2
@
@
+2 +2
+2 +2
3 3


> >
> >


+2
+2
3 3
+2
+2
3 3
4=3"dimethylbutane
4=3"dimethylbutane

(! there are two chains o! eAual length as
(! there are two chains o! eAual length as
the parent chain= choose the
the parent chain= choose the
chain with
chain with
the greater number o! substituents.
the greater number o! substituents.

9 5 ' 3 3 4 1
4=3='"trimethyl"3"propylheptane
#!our substituents$
+2
3
+2
4
"+2 +2 +2 +2+2
3
> > > >
+2
3
+2
4
+2
3
+2
3
>
+2
4
>
+2
3
3 3 4 1
'
5
9
3"sec"butyl"4=3"dimethylheptane
#three substituents$

(! branching occurs at an eAual distance !rom
(! branching occurs at an eAual distance !rom
either end o! the longest chain= choose the
either end o! the longest chain= choose the
name that gi,es the
name that gi,es the
lower number at the !irst
lower number at the !irst
point o! di!!erence.
point o! di!!erence.
5 ' 3 3 4 1
+2
3
+2+2
4
+2 +2+2
3
> > >
+2
3
+2
3
+2
3
4=3='"trimethylhe.ane
#N:/ 4=3='"trimethylhe.ane$
1 4 3 3 ' 5

CYCOA!AN"S
CYCOA!AN"S
Cycloalkanes alkanes which carbon
Cycloalkanes alkanes which carbon
atoms are !oined in
atoms are !oined in
rings
rings
.
.
Cycloalkanes are known as saturated
Cycloalkanes are known as saturated
hydrocarbon, because it has the
hydrocarbon, because it has the
maximum number of bonded hydrogen
maximum number of bonded hydrogen
" only has single bonds#.
" only has single bonds#.
$eneral formula:
$eneral formula:
C
C
n n
H
H
#n #n
where
where
n $ 3% &% '% ((
n $ 3% &% '% ((

%&'E%C()*+E &,
%&'E%C()*+E &,
C-C(&)(.)%E/
C-C(&)(.)%E/
Cycloalkanes
Cycloalkanes
with only one ring
with only one ring
are
are
named with
named with
the prefix cyclo- to the
the prefix cyclo- to the
names of the alkanes
names of the alkanes
"contain the
"contain the
same number of carbon atoms#
same number of carbon atoms#

E:a"6les7 )onocyclic co"6ounds
+
3
2
5
cyclopropane
+
3
2
7
cyclobutane
+
'
2
1%
cyclopentane

0f only one substituent is present, it is
0f only one substituent is present, it is
not
not
necessary to designate its position
necessary to designate its position
.
.
Examples:
Examples:
+2
3

+hlorocyclopropane
1ethylcyclohe.ane
+l

0f two substituents are present,
0f two substituents are present,
number carbon in the ring beginning
number carbon in the ring beginning
with the substituent according to the
with the substituent according to the
alphabetical order
alphabetical order

and
and
number in the direction that gi1es
number in the direction that gi1es
the next substituent
the next substituent
the lowest
the lowest
number
number
possible.
possible.

E:a"6les7
1"ethyl"4"methylcyclohe.ane
N:/
1"ethyl"5"methylcyclohe.ane
+2
3
+2
4
+2
3
1
.
2
<
=
;

1=3"dichlorocyclopentane
#N:/ 1='"
dichlorocyclopentane$
+l +l
1
.
2
< =

Bhen three or more substituents are
present= begin at the carbon with
substituent that leads to the lowest set o!
locants.

E.ample:
+2
4
+2
3
1"chloro"3"ethyl"3"
methylcyclohe.ane
3" chloro"4"ethyl"1"
methylcyclohe.ane
+l +2
3
Locants
chloro
ethyl
methyl
1
3
3
1
4
3
1
.
2
<
=
;
1
.
2
<
= ;

1"ethyl"1=3"dimethylcyclopentane
#N:/ 3"ethyl"1=3"dimethylcyclopentane$
2
3
+ +2
4
+2
3
+2
3

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 o! + at ring
Number o! + at
linear chain

1=3"dicyclohe.ylpropane
1
.
2

E.amples:
+2
4
+2
4
+2
4
+2
4
+2
3
1"cyclobutylpentane