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Degree of Unsaturation in Organic Compounds: Rings, Bonds, and Groups, Slides of Molecular Chemistry

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.

What you will learn

  • What is the process for calculating the Degree of Unsaturation of a compound containing multiple functional groups?
  • How is the Degree of Unsaturation calculated for hydrocarbons?
  • What is the difference between an acyclic alkene and a cycloalkane?
  • What happens when two hydrogen atoms on non-adjacent carbons in a hydrocarbon are removed?
  • How does the presence of halogens, oxygen, or nitrogen affect the Degree of Unsaturation of a hydrocarbon?

Typology: Slides

2021/2022

Uploaded on 09/12/2022

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Degree of Unsaturation
How to determine the number
of rings and multiple bonds in a
compound from its molecular formula
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Degree of Unsaturation

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

H

2n+ All such compounds are acyclic The number of hydrogens is always even.

then a ring, cyclobutane (C 4

H

8 ), is formed with the loss of H 2 If two hydrogen atoms on non-adjacent carbons of n-butane (C 4

H

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

H

10

are removed a double bond is formed with the loss of H 2

In this case, the alkene, 1 - butene (C 4

H

8 ), is formed.

Try the following formulas: C 6

H

6 C 7

H

10 C 10

H

8

norbornene naphthalene

DU

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

H

5 BrCl 2 1 DU - C 6 3 DU 1 DU - C 8 Br Br Cl Cl Cl 2

C

8

5 DU

H

H

H

H

H

H

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

C

8

H

6 Cl 2

O

3 2,4-Dichlorophenoxyacetic acid C 8

H

18

- C

8

H

8

= H

10

/ 2 = 5 DU

C

8

H

6 Cl 2 (drop O 3 )

C

8

H

8 (- Cl 2 + H 2 )

pyridine C 5

H

5

N

benzene C 6

H

6 (- N + CH) C 6

H

14

- C

6

H

6

= H

8

/ 2 = 4 DU

= H

16

/ 2 = 8 DU

Cocaine - C 17

H

21

NO

4 C 17

H

21

NO

4

C

17

H

21

N

C

18

H

22 C 18

H

38

- C

18

H

22 4 DU 1 DU

1 DU

1 DU

(6-membered ring)

1 DU

(5-membered ring)