Date- 28-10-2020

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REACTION OF THE DAY

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: tert. alkyl > sec. alkyl, aryl > prim. alkyl > CH3.
Mechanism of the Baeyer-Villiger Oxidation

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

 

(1)
 Try Yourself

O
Et O

m-CPBA, Li2CO3
O Product
CH2Cl2,RT
1. O

COOEt
EtOOC

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 (3)



(2)