Michael addition was discovered by Arthur Michael in 1887. Michael’s addition reaction is one of the most useful methods for the mild formation of C–C bonds. The Michael reaction or Michael addition is the nucleophilic addition of a carbanion or another nucleophile to an α, β-unsaturated carbonyl compound containing an electron-withdrawing group. It belongs to the larger class of conjugate additions. In this article, we discuss the definition, examples, application, and mechanism of Michael’s addition.
What are addition reactions?
An addition reaction is a chemical reaction where two or more reactants come together to form a large single product. Only chemical compounds containing multiple bond characters can undergo an addition reaction as a double or triple bond is usually broken to form the required single bonds.
An addition reaction is essentially a reverse decomposition reaction.
Definition of michael addition reaction
The Michael reaction or Michael addition is the nucleophilic addition where an electrophile(a compound which forms bonds by accepting a lone pair of electrons) with a double or triple bond reacts with a nucleophile(a compound which forms bonds by donating a lone par of electron) in such a way that the double or triple bond of the electrophile breaks.
Aneta Pospisilova, CC BY-SA 4.0 https://creativecommons.org/licenses/by-sa/4.0, via Wikimedia Commons
Examples of michael’s addition reaction
•Diethyl malonate (a three-carbon dicarboxylic acid ) with methyl crotonate.
•Diethyl malonate with diethyl fumarate.
•Mesityl oxide with diethyl malonate.
•Nitropropane with methyl vinyl ketone.
•2-Nitropropane with methyl acrylate.
Mechanisim of Michael’s addition reaction:
Eva1900, CC0, via Wikimedia Commons
Application of michael’s addition reaction
The Michael addition is a simple reaction between nucleophiles and activated olefins and alkynes in which the nucleophile adds across carbon-carbon multiple bonds. Some of the important applications are:
Hydrogenation of vegetable oils is used to add hydrogen to oils in the presence of a catalyst to convert them into vegetable ghee.
Applications of Michael’s addition reaction in the synthesis of natural products and complex compounds with biological activities were summed up.
