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REACTION OF THE DAY-02

Chemistry

Baeyer-Villiger Oxidation

The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which
converts ketones to esters and cyclic ketones to lactones. The Baeyer-Villiger can be carried out with peracids,
such as MCBPA, or with hydrogen peroxide and a Lewis acid.
The major product of the reaction depends on the relative migratory ability of the substituents attached to the
carbonyl. Substituents which are able to stabilize a positive charge migrate more readily, so that the order of
preference is:

3° 2° 1°
H >> alkyl > Cy > alkyl > Bn  Ph > alkyl > cyclopropyl > CH3

R R
H R CH 3
R R Ph R

Mechanism of the Baeyer-Villiger Oxidation

(1)
 O O
.. + ..
O: H—O—O—C—R O—H O—O—C—R :O—H
O
O—O—C—R

O O—H O—H
O
C  C C
O –H O
O + R—C—O
 

-Lactone



(2)
 Try Yourself
1. The major product expected when 2,3-dimenthylcyclohexanone is treated with mCPBA is:

O
mCPBA
CH2Cl2

O O
O

(1) (2) O

O O
O

O
(3) (4)

2. The major product formed in the Baeyer villiger oxidation of camphor with mCPBA and NaHCO3 is :

mCPBA
NaHCO 3
O

O
(1) (2)
O
O
O

HO
O

(3) O (4)

O
OH

(3)
 CF3CO 3H
X
3. CH 2Cl2

O Ph

OH HO OH
(1) (2)

O Ph O Ph

(3) (4) O

O OPh O Ph

Ph O
H
O F3C
*
O–O
4.

Ph Ph
O
O*
(!) (2)
O
O

Ph Ph
O
O
(3) (4)
O*
O

O
Et O

m-CPBA, Li2CO3
O Product
CH2Cl2
5. O

COOEt
EtOOC

(4)
Find out the product which is formed after the reaction

O O
O
Et O O
Et
O
O
(1) O (2)
O O
EtOOC
COOEt
COOEt EtOOC

O O
O O
Et Et

O O O O
(3) O (4)
O

EtOOC EtOOC
COOEt COOEt

Answers of questions based on Aldol reaction

1. Answer (4)
2. Answer (4)
3. Answer (2)
4. Answer (1)
5. Answer (3)

(5)