Post on 15-Dec-2014
description
Favorskii Rearrangement
By Sagar DivetiyaEnvironment science and technology (4th sem)
110990135013
Organic Chemistry for technologist II
2Outline
• Principle
• Some reactions
• Mechanism ( Cyclic Ketone )
• Mechanism ( Open chain Ketone )
• Applications
10/04/2023 04:07 AMPrepared by Sagar Divetiya
3Principle
• 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.
10/04/2023 04:07 AMPrepared by Sagar Divetiya
4
10/04/2023 04:07 AMPrepared by Sagar Divetiya
Some reactions
Ester
Ketone
Carboxylic acid
Carboxylic acid
Ester
Alkoxide
Hydroxide
α-halogenated
5Mechanism ( Cyclic Ketone )
Cl O
H
Cl ORO
O
RO
OR
O
RO
H
HO
OR
Favorskii
Rearrangemen
t
10/04/2023 04:07 AMPrepared by Sagar Divetiya
- H- Cl1 2 3
45
6Mechanism ( Open Chain Ketone)
10/04/2023 04:08 AMPrepared by Sagar Divetiya
H X
OR’ RO
X
OR’ O
RO
O OR
RO
H
OOR
R’
R’R’
O OR
R’
Favorskii Rearrangeme
nt
H
1 2 3
456
8Applications
10/04/2023 04:08 AMPrepared by Sagar Divetiya
9Applications
10/04/2023 04:08 AMPrepared by Sagar Divetiya