The degree of unsaturation/index of hydrogen deficiency is used in organic

chemistry to help draw chemical structures. The formula lets the user determine
how many rings, double bonds, and triple bonds are present in the
compound to be drawn. It does not give the exact number of rings or double or
triple bonds, but rather the sum of the number of rings and double bonds plus twice
the number of triple bonds.

The formula for IHD is:

IHD = (2C+2-X-H+N)/2

C = no. of carbons
X = no. of halides (i.e., F, Cl, Br, I)
H = no. of hydrogens
N = no. of nitrogens

**** AN IHD OF

1
1
2
4

=
=
=
=

1
1
1
1

double bond
ring
triple bond
benzene ring

Examples:
1.

2.

3.

4.

5.

CHCl3 (how do you name this compound? Note both systematic and common
nomenclatures)
IHD = [(2x1)+2-3-1]/2
IHD = 0 (no rings, no double bonds, etc.)
Propylene glycol
IHD = 0 (why?)
Glycerol
IHD = 0 (why?)
C2 H 4
IHD = 1
Possibilities: double bond and ring. But since it has only 2 carbons, it cannot
have a ring. Therefore this compound has a double bond.
C4 H 6
IHD = 2

Possibilities:

a. 1 double bond + 1 ring such as

b. 2 double bonds
c. 2 rings
d. Triple bond

Practice Problems:

Answers:

More Problems:
What is the IHD of:
1.
2.
3.
4.
5.
6.
7.
8.

1-pentyn-4-ol
Acetophenone
Acetamide
Anisole
Salicylic acid
Limonene
T.N.T. (an explosive chemical)
1-ethenyl-2-buten-1-ol