Favorskiirearrangementoct 130921133027 Phpapp01

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Organic Chemistry for technologist II

Favorskii
Rearrangement
By Sagar Divetiya
Environment science and technology (4th sem)
110990135013
Outline 2

• Principle

• Some reactions

• Mechanism ( Cyclic Ketone )

• Mechanism ( Open chain Ketone )

• Applications

Prepared by Sagar Divetiya 19/11/2024 06:49 PM


Principle 3

• α-Halogenated ketone undergoes rearrangement in


the presence of a base like hydroxide, alkoxide or
amine to give a carboxylic acid or its derivative i.e.
ester, amide. The reaction is known as Favorskii
rearrangement.

• The halogen may be a chloride, bromide or iodide.


Este

α- Alkoxide
r 4
halogenated
Este
Hydroxid r
e

Carboxylic
acid Some
reactions
Carboxylic
acid

Keton
e
Prepared by Sagar Divetiya 19/11/2024 06:49 PM
Mechanism ( Cyclic Ketone ) 5

Cl O

1 H
R
O
-H
Cl O

2 - Cl
O

3 R
O
Re F
a r a vo
ra rs
ng k
t em i i
en

4
O O O

5
H
O R
R
R H
Prepared by Sagar Divetiya
O 19/11/2024 06:49 PM
Mechanism ( Open Chain
Ketone) 6

2
O

1
R’ RO R’

3
O
R’
H X X
RO
Favorskii
Rearrangeme
nt

4
O O

5
O O
O

6
O R
R R
R’ R’
R H
R’ H O
Prepared by Sagar Divetiya 19/11/2024 06:49 PM
Applications 8

Prepared by Sagar Divetiya 19/11/2024 06:49 PM


Applications 9

Prepared by Sagar Divetiya 19/11/2024 06:49 PM

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