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How to calculate the Degree of Unsaturation (DU) of organic compounds by identifying rings, multiple bonds, and functional groups. It covers hydrocarbons, halogens, oxygen, and nitrogen-containing compounds. The process involves comparing the molecular formula of the compound to the most saturated hydrocarbon and dividing the difference by 2.
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How to determine the number of rings and multiple bonds in a compound from its molecular formula
No hydrocarbon can contain a greater number of hydrogens than fits the formula C n
2n+ All such compounds are acyclic The number of hydrogens is always even.
then a ring, cyclobutane (C 4
8 ), is formed with the loss of H 2 If two hydrogen atoms on non-adjacent carbons of n-butane (C 4
10
are removed This process is not necessarily a chemical reaction but rather a conceptual device.
then If two hydrogen atoms on adjacent carbons of n-butane (C 4
10
are removed a double bond is formed with the loss of H 2
In this case, the alkene, 1 - butene (C 4
8 ), is formed.
Try the following formulas: C 6
6 C 7
10 C 10
8
norbornene naphthalene
benzene Example
How is the Degree of Unsaturation of a hydrocarbon containing halogen, or other monovalent atom, determined? Every halogen in a hydrocarbon replaces a hydrogen.
One example of an alkyl halide C 8
5 BrCl 2 1 DU - C 6 3 DU 1 DU - C 8 Br Br Cl Cl Cl 2
8
5
How is the Degree of Unsaturation of a hydrocarbon containing oxygen, or other divalent atom, determined?
2,4-Dichlorophenoxyacetic acid benzene ring - 4 DU carbonyl - 1 DU
8
6 Cl 2
3 2,4-Dichlorophenoxyacetic acid C 8
18
8
8
10
8
6 Cl 2 (drop O 3 )
8
8 (- Cl 2 + H 2 )
pyridine C 5
5
benzene C 6
6 (- N + CH) C 6
14
6
6
8
16
Cocaine - C 17
21
4 C 17
21
4
17
21
18
22 C 18
38
18
22 4 DU 1 DU
(6-membered ring)
(5-membered ring)