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OPPENEAUR REACTION
Presented By:
Chayan Mondal
ID: 181814
Chemistry Discipline
Khulna University
Oppenauer Oxidation is the process of conversion of secondary alcohols to
ketones by selective oxidation. This reaction is named after Rupert Viktor
Oppenauer. Oxidation reaction takes place in the presence of [Al(i-Pro)3] in excess
of acetone.
It is an aluminium alkoxide catalysed oxidation of a secondary alcohol to the
corresponding ketone. This is the reverse of the Meerwein Ponndorf Verley
reduction. It is a very good method to oxidise allylic alcohols to α, β- unsaturated
ketones.
CH3
H3C
O
R2
R1
OH
R2
R1
O
CH3
H3C
OH
Al(i-PrO)3 /heat
INTRODUCTION
There are five steps---
1.In the first step, alcohol coordinates with aluminium isopropoxide to form
a complex
2.This complex reacts with a ketone to form a six-membered transition
complex
3.The alpha-carbon of the alcohol is converted to the carbonyl carbon from
the aluminium-catalysed hydride shift.
4.The acetone proceeds over a six-membered transition state.
5.The desired ketone is formed after the hydride transfer
Oppenauer Oxidation Mechanism
Oppenauer Oxidation Mechanism