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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.

Saturated Hydrocarbons FORMATION OF RINGS AND 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
also follow the formula

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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

Formation of each ring or double bond causes the loss of 2H.

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

C4H11N add one H for 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

F, Cl, Br, I -- subtract one H from calculated


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
hydrogen and a palladium catalyst
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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A FEW POSSIBLE ANSWERS


CH3
CH3

H3C CH3

CH3

CH2CH3

..... there is still work required to fully solve the problem