Favorskii rearrangement is one the important reactions in organic chemistry. Let us have some prior understanding of its mechanism and its applications.

1. Favorskii
Rearrangement
By Sagar Divetiya
Environment science and technology (4th sem)
110990135013
Organic Chemistry for technologist II

2. Outline
• Principle
• Some reactions
• Mechanism ( Cyclic Ketone )
• Mechanism ( Open chain Ketone )
• Applications
9/21/2013 11:30 AMPrepared by Sagar Divetiya
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3. Principle
• 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.
9/21/2013 11:30 AMPrepared by Sagar Divetiya
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4. 9/21/2013 11:30 AMPrepared by Sagar Divetiya
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Some
reactions
Ester
Ketone
Carboxylic acid
Carboxylic acid
Ester
Alkoxide
Hydroxide
α-halogenated

5. Mechanism ( Cyclic Ketone )
Cl O
H
Cl O
RO
O
RO
ORO
RO H
H
O
OR
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- H
- Cl
1 2 3
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6. Mechanism ( Open Chain Ketone)
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H X
O
R’ RO
X
O
R’ O
RO
O OR
RO H
O
OR
R’
R’R’
O OR
R’
Favorskii
Rearrangement
H
1 2 3
456

7. Applications
9/21/2013 11:30 AMPrepared by Sagar Divetiya
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8. Applications
9/21/2013 11:30 AMPrepared by Sagar Divetiya
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