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# 2/22/2016

KIM3204
WHAT CAN YOU LEARN FROM A
STRUCTURAL IDENTIFICATION OF
MOLECULAR FORMULA ?
CHEMICAL COMPOUNDS

## CHAPTER 1 (Cons) YOU CAN DETERMINE THE NUMBER OF

RINGS AND / OR DOUBLE BONDS.

## Notice that the general formula for the compound,

CnH2n+2 GENERAL FORMULA
, changes when a double or triple bond is
CH4
present:
CH4
CH3CH3 C2H6

CH3CH2CH3 C3H8

CH3CH2CH2CH3 C4H10

CH3CH2CH2CH2CH3 C5H12
Adding a degree of unsaturation decreases the
CH3 CH3 number of H atoms by two.
CH3 CH CH C CH3 C9H20

CH3 CH3
branched compounds

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## FORMATION OF RINGS AND DOUBLE BONDS Index of Hydrogen Deficiency

-2H Index of Hydrogen Deficiency (IHD): the sum of the number
C C C C of rings and pi bonds in a molecule.
H H

## H H To determine IHD, compare the number of hydrogens in

-4H
an unknown compounds equivalent hydrocarbon with the
C C C C
number in a reference hydrocarbon of the same number of
H H carbons and with no rings or pi bonds
CH2 CH2
H2C -2H H2C CH2
CH2 H the molecular formula of the reference hydrocarbon is
H2C CH2 H H2C CH2 CnH2n+2
CH2 CH2

## Index of Hydrogen Deficiency Index of Hydrogen Deficiency

Summary of how the index of hydrogen deficiency works
Example 1 : A compound with molecular formula C6H12
 A double bond and ring each counts as one IHD
 A triple bond counts as two IHD C6H14 = formula corresponding alkane (hexane)
C6H12 = formula of compound (1-hexene or cyclohexane)
CALCULATION METHOD H2 = difference = 1 pair of hydrogen atoms
IHD = 1
Determine the expected formula for a noncyclic, saturated
compound ( CnH2n+2 ) with the same Example 2 : A compound with molecular formula C5H8
number of carbon atoms as your compound.

C5H12 = ( CnH2n+2 )
Correct the formula for heteroatoms
C5H8
Subtract the actual formula of your compound
H4 Two Unsaturations
Index = 4/2 = 2
double bond and
ring in this example

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## Index of Hydrogen Deficiency Example 3 : A compound with molecular formula C4H5N

CORRECTIONS FOR ATOMS OTHER THAN HYDROGEN
H
O or S -- doesnt change H in calculated formula (Ignore) C4H10 = ( CnH2n+2 ) N

+0 C-H
+O
C-O-H
C 4 H5 N

## N or P -- add one H to the calculated formula

H6

C-H C-NH2
+1 +N,+H Index = 6/2 = 3 two double bonds and
ring in this example

formula
-1 C-H
-H,+X
C-X

## PROBLEM A hydrocarbon has a molecular

The index gives the number of formula of C6H8. It will react with
double bonds or to give a compound of formula
C6H12. Give a possible structure.
triple bonds or

rings in a molecule
one ring and the INDEX C6H14
equivalent of three
Benzene double bonds gives -C6H8
an index of 4
H6 Index = 6/2 = 3

HYDROGENATION
If index = 4, or more, Pd
C6H8 + 2 H2 C6H12
expect a benzene ring
Hydrogenation shows only two double bonds.
Therefore, there must also be a ring.

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