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Index of Hydrogen Deficiency

The index of hydrogen deficiency is a measure of unsaturation in organic molecules, calculated by comparing the molecular formula to a hypothetical saturated structure. It indicates the number of pi bonds and/or rings in a molecule. A compound with an index of one can have one double bond or one ring. Benzene has an index of four due to its aromatic ring. To determine the index, the formula for a saturated hydrocarbon of the same carbon number is adjusted for other elements and compared to the substance's formula.

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134 views10 pages

Index of Hydrogen Deficiency

The index of hydrogen deficiency is a measure of unsaturation in organic molecules, calculated by comparing the molecular formula to a hypothetical saturated structure. It indicates the number of pi bonds and/or rings in a molecule. A compound with an index of one can have one double bond or one ring. Benzene has an index of four due to its aromatic ring. To determine the index, the formula for a saturated hydrocarbon of the same carbon number is adjusted for other elements and compared to the substance's formula.

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maheen aurangzaib
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Index of hydrogen deficiency

The index of hydrogen deficiency (sometimes called the


unsaturation index) is the number
of p bonds and/or rings a molecule contains. It is determined
from an examination of the molecular formula of an unknown
substance and from a comparison of that formula with a
formula for a corresponding acyclic, saturated compound. The
difference in the number of hydrogens between these formulas,
when divided by 2, gives the index of hydrogen deficiency.
Compound with an index of one must have one double bond or one ring, but it cannot have both
structural features. A quick examination of the infrared spectrum could confirm the
presence of a double bond. If there were no double bond, the substance would have to be cyclic
and saturated.
A compound with an index of two could have a triple bond, or it could have two
double bonds, two rings, or one of each. Knowing the index of hydrogen deficiency of a substance,
the chemist can proceed directly to the appropriate regions of the spectra to confirm the presence
or absence of p bonds or rings.
Benzene contains one ring and three “double bonds” and thus has
an index of hydrogen deficiency of four. Any substance with an index of four or more may contain
a benzenoid ring; a substance with an index less than four cannot contain such a ring.
To determine the index of hydrogen deficiency for a compound, apply the following steps:
1. Determine the formula for the saturated, acyclic hydrocarbon containing the same number
of carbon atoms as the unknown substance.

2. Correct this formula for the nonhydrocarbon elements present in the unknown. Add one
hydrogen atom for each Group V element present and subtract one hydrogen atom for each
Group VII element present.

3. Compare this formula with the molecular formula of the unknown. Determine the number of
hydrogens by which the two formulas differ.

4. Divide the difference in the number of hydrogens by two to obtain the index of hydrogen
deficiency. This equals the number of p bonds and/or rings in the structural formula of the
unknown substance.
The unknown substance has the molecular formula C7H14O2.

1. Using the general formula for a saturated, acyclic hydrocarbon (CnH2n12, where n 5
7), calculate the formula C7H16.

2. Correction for oxygens (no change in the number of hydrogens) gives the formula
C7H16O2.

3. The latter formula differs from that of the unknown by two hydrogens.

4. The index of hydrogen deficiency equals one. There must be one ring or one
double bond in
the unknown substance
THE RULE OF THIRTEEN

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