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SINHA’s I. I.T.

CHEMISTRY -1-

Problem solving skill to find no of structural isomers .


In general, the students find it difficult to identify the no of isomers for any given molecular
formula. Here is a more convenient and systematic approach developed by S.K.Sinha ,kota
(India).

Step 1: Find the index of Hydrogen deficiency using the Formula


For any compound with molecular formula
CnHmClxOyNz
where
n==no of carbon
m=no of hydrogen
x= no of monovalent atoms like F,Cl, Br,I, D ,T etc
y= no of divalent like O
z= no of trivalent like N.

2n+2-m-x+z
I = Where I = index of hydrogen deficiency

Ex. For C6H6 I=(6X2+2-6)/2 =8/2 =4.


Here I is the sum of total no of cycles(rings)
Step -2 Write all possible carbon sleletons for given formula.
CH3

CH3
Ex C4H10 H3C &
H3C CH3
CH3 H3C
CH3
Ex C5H12 H3C CH3 H3C

H3C
CH3 CH3
CH3
H3 C CH3
CH3
Ex C6H14 CH3
H3C H3C CH3

CH3 CH3

H3C CH3
CH3 H3 C
H3C

CH3

1-D-10 Talwandi & B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055


SINHA’s I. I.T. CHEMISTRY -2-

Step-3 :-Find all possible functional group for the given molecular formula using index of
hydrogen deficiency.
Ex C3H6O here index =(2X3+2-6)/2 =1
Index 1 means 1 pi bond or one cycles.
Let there is 1 Pi bond
1. pi with c=c then O must be as --OH or --OR
OH
OH CH3
H2C CH3
a H2C CH3 HO c H2C O
b
d
here b & C are unstable as they are enol and not counted as isomers.
2 . pi with c=O then C must be as ------R
O
O
H3C
H3C a CH3 b
H
Let there is one cycle .
The cycle may be with carbon only as cyclopropane ,
Or the cycle may include O also as below.
O O

CH3
a c
b
4 Arrange all possible functional groups on all possible carbon chains.and remove the
structures with unstable functional groups.For above given problem the total structural
isomers possible are …………………..
O
OH CH3 O
H2C H2C O H3C
a b d
c H
H3C CH3
OH

O O

e CH3
f
g

1-D-10 Talwandi & B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

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