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