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Chemistry · Glossary

What is Michael addition?

Also known as: Michael donor · Michael acceptor

Definition 26.6 University Chemistry — Year 2 · Chapter 26 — Conjugated Carbonyls: Michael and Robinson

A Michael addition is the conjugate addition of a stabilised carbanion, usually an enolate, to an α,β\alpha,\beta-unsaturated carbonyl compound or a similar electron-poor alkene. The nucleophile is the Michael donor (a 1,3-dicarbonyl compound, a nitroalkane, a cyanoester); the unsaturated compound is the Michael acceptor (an enone, an enal, an unsaturated ester, nitrile or nitro compound).

The Michael addition of diethyl propanedioate to but-3-en-2-one. Ethoxide forms the stabilised enolate; it adds to the  carbon; the enolate formed takes a proton from ethanol, which regenerates ethoxide. The product, diethyl (3-oxobutyl)propanedioate, is a 1,5-dicarbonyl compound. The Michael addition of diethyl propanedioate to but-3-en-2-one. Ethoxide forms the stabilised enolate; it adds to the  carbon; the enolate formed takes a proton from ethanol, which regenerates ethoxide. The product, diethyl (3-oxobutyl)propanedioate, is a 1,5-dicarbonyl compound.
The Michael addition of diethyl propanedioate to but-3-en-2-one. Ethoxide forms the stabilised enolate; it adds to the β\beta carbon; the enolate formed takes a proton from ethanol, which regenerates ethoxide. The product, diethyl (3-oxobutyl)propanedioate, is a 1,5-dicarbonyl compound.
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