3
N O M E N C L A T U R E IN O R G A N IC C H E M IS T R Y
1 .
IN T R O D U C T IO N
It is im p o rta n t th a t o rg a n ic c o m p o u n d s a re c o rrre c tly a n d u n a m b ig u o u s ly n a m e d s o th a t th e re
c a n b e a b s o lu te ly n o c o n fu s io n a b o u t w h a t c o m p o u n d s a re a c tu a lly b e in g re p o rte d o r
d e s c rib e d . T h e re h a v e b e e n m a n y c o n v e n tio n s fo r n a m in g o rg a n ic c o m p o u n d s - s o m e h a v e
h a d lim it s c o p e o r b e c o m e e m b e d d e d in c o m m o n u s a g e a n d s o m e h a v e p e r s is te d o v e r tim e
T h e In te rn a tio n a l U n io n o f P u re a n d A p p lie d C h e m is try (I.U .P .A .C .) p e rio d ic a lly re v ie w s
n a m in g p ra c tic e , a tte m p tin g to s ta n d a rd is e n o m e n c la tu re . T h e fo llo w in g g u id e lin e s fo r
o rg a n ic n o m e n c la tu re a re b a s e d o n th e d e fin itiv e ru le s p u b lis h e d b y I.U .P .A .C .
1
(th e
In te rn a tio n a l U n io n o f P u re a n d A p p lie d C h e m is try ).
2 .
H Y D R O C A R B O N S
( i)
T h e A lk a n e s (Cn H2 n + 2 )
A .
U n b ra n c h e d C h a in s
T h e firs t fo u r (n = 1 -4 ) u n b ra n c h e d c h a in s a tu ra te d h y d ro c a rb o n s a re c a lle d m e th a n e , e th a n e ,
p ro p a n e a n d b u ta n e . A fte r th is , th e re is a n u m e ric a l te rm (o f G re e k o rig in ) fo llo w e d b y th e
e n d in g " -a n e " . T h e firs t tw e lv e m e m b e rs a re g iv e n in T a b le 1 .
T a b le 1 .
T h e n a m e s o f th e fir s t 1 2 lin e a r a lk a n e s
n
N am e
M o le c u la r fo r m u la
C o n s titu tio n a l fo rm u la
1
m e th a n e
C H4
C H4
2
e th a n e
C2H 6
C H3 C H3
3
p ro p a n e
C3H 8
C H3 C H2 C H3
4
b u ta n e
C4H 1 0
C H3 C H2 C H2 C H3
5
p e n ta n e
C5 H1 2
C H3 C H2 C H2 C H2 C H3
6
h e x a n e
C6H 1 4
C H3 C H2 C H2 C H2 C H2 C H3
7
h e p ta n e
C7H 1 6
C H3 C H2 C H2 C H2 C H2 C H2 C H3
8
o c ta n e
C8H 1 8
C H3 C H2 C H2 C H2 C H2 C H2 C H2 C H3
9
n o n a n e
C9H 2 0
C H3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3
1 0
d e c a n e
C1 0H 2 2
C H3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3
1 1
u n d e c a n e
C1 1H 2 4
C H3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3
1 2
d o d e c a n e
C1 2H 2 6
C H3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3
T h e g ro u p d e riv e d fro m o n e o f th e s e a lk a n e s b y re m o v a l o f a te rm in a l (e n d ) h y d ro g e n is
c a lle d a n a lk y l g ro u p . T h e g ro u p n a m e is fo u n d b y re m o v in g " a n e " fro m th e a lk a n e n a m e
a n d a d d in g " y l" .
E x a m p le :
C H3-C H 2-C H 2-C H 3
b u ta n e
becom es
C H3 -C H2 -C H2 -C H2 -
b u ty l
N o te: T h e fre e v a le n c e m u s t b e o n th e te rm in a l c a rb o n .
1
I.U .P .A .C . N o m e n c la tu re fo r O rg a n ic C h e m is try, S e c tio n s A , B a n d C ( c o m b in e d e d itio n ) ,
B u tte rw o rth s S c ie n tific P u b lic a tio n s , L o n d o n , 1 9 7 1 .
4
B .
B ra n c h e d C h a in s
T h e fo llo w in g s te p s a r e ta k e n in n a m in g a n a lk a n e w ith a b r a n c h e d c h a in :
(a )
F in d th e lo n g e s t c o n tin u o u s c a rb o n c h a in a n d s e le c t th e a p p ro p ria te a lk a n e n a m e
fro m T a b le 1 . (S id e c h a in s a re n o t in c lu d e d in th e c a rb o n c o u n t.)
(b )
N a m e a ll o f th e s id e c h a in s ( c a r b o n c h a in s a tta c h e d to th e lo n g e s t c h a in ) a n d lis t
th e m in a lp h a b e tic a l o rd e r. Ig n o re m u ltip lic a tiv e p re fix e s s u c h a s \u201cd i-\u201c (2 ), \u201ctri-\u201c
(3 ), "te tra -" (4 ) e tc . A ls o ig n o re "s e c -" a n d "te rt -" b u tn o t "is o ".
(c )
N u m b e r th e lo n g e s t c h a in s o th a t s u b s titu e n ts h a v e th e lo w e s t p o s s ib le n u m b e rs
a n d in s e rt lo c a tio n n u m b e rs b e fo re e a c h o f th e s id e c h a in n a m e s .
S p e c ia l N o te: T h e fo llo w in g g r o u p s h a v e th e s p e c ia l n a m e s in d ic a te d :
C H3
C H
C H3
is o p ro p y l
C H3
C H
C H3
C H2
is o b u ty l
C H3
C H
C H3
C H3
s e c o n d a ry -b u ty l
s e c -b u ty l
s-b u ty l
C H3
CC H3
C H3
te rtia ry -b u ty l
te rt-b u ty l
t-b u ty l
E x a m p le s
C H3
C H2
C H
C H2
C H3
C H3
3 -m e th y lp e n ta n e
C H3
C H
C H2
C H
C H
C H3
C H3
C H2
C H3
C H3
2 ,4 ,5 -trim e th y lh e p ta n e
(n o t 3 ,4 ,6 -)
C H3
C H2
C H2
C H
C H2
C H
C H
C H3
C H3
C H3
C H3
C H3
4 -is o p ro p y l-2 ,2 -d im e th y lo c ta n e
C H3
C H2
C H2
C H
C H
C H2
C H2
C H2
C H3
C H3
C H3
4 -e th y l-5 -m e th y lo c ta n e
(n o t 5 -e th y l-4 -m e th y lo c ta n e )
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