Table of Contents
Michael Reaction Mechanism ; Michael Addition Reaction Mechanism ;
The Michael addition reaction mechanism is a three-step process in which a nucleophile, such as an alcohol, attacks a carbonyl group in a molecule, creating a new carbon-carbon bond. The second step is the migration of the leaving group, which is typically a hydrogen atom, to the other side of the new carbon-carbon bond. The third and final step is the elimination of water from the molecule.
Michael Addition Reaction With Mechanism
The Michael addition reaction is a type of organic reaction in which a carbon-carbon double bond is attacked by an enolate, an alkoxide ion derived from a ketone or aldehyde. The Michael addition reaction is named after the organic chemist Michael Smith, who first reported it in 1952.
The general form of the Michael addition reaction is shown below.
RC=CR’ + R’C=O → RC=C(R’)+O
In the Michael addition reaction, the carbon-carbon double bond is attacked by the enolate. The enolate is formed by the deprotonation of the ketone or aldehyde. The deprotonated ketone or aldehyde is then converted into the enolate ion by the addition of a strong base.
The mechanism of the Michael addition reaction is shown below.
In the first step, the carbon-carbon double bond is attacked by the enolate. The enolate forms by the deprotonation of the ketone or aldehyde. The deprotonated ketone or aldehyde is then converted into the enolate ion by the addition of a strong base.
In the second step, the enolate ion attacks the carbon-carbon double bond. The enolate ion forms by the addition of a strong base to the deprotonated ketone or aldehyde. The addition of the strong base converts the deprotonated ket
Example of Compounds Showing Michael’s Addition Reaction
When two molecules of an alpha, beta-unsaturated ketone react with one molecule of formaldehyde in the presence of an acid catalyst, they form a hemiketal. The hemiketal then reacts with a second molecule of formaldehyde to form a fully saturated ketone. This reaction is called the Michael addition reaction.
The following diagram shows the Michael addition reaction of acetone and formaldehyde.
In the diagram, the red lines indicate the electron pairs that are shared between the carbon atoms in the ketone molecules. The blue lines indicate the electron pairs that are shared between the carbon atom and the oxygen atom in the formaldehyde molecules.
The first step in the Michael addition reaction is the formation of a hemiketal. In the hemiketal, the electron pairs in the carbon-oxygen bonds in the ketone molecules are shared with the electron pairs in the carbon-carbon bonds in the formaldehyde molecules. This creates a four-membered ring.
The second step in the Michael addition reaction is the formation of a fully saturated ketone. In the fully saturated ketone, the electron pairs in the carbon-carbon bonds are shared between the carbon atoms. This creates a three-membered ring.
Mukaiyama-Michael Addition Reaction
The Mukaiyama-Michael addition reaction is a type of organic reaction that involves the addition of an alkene to an imine. The reaction is named for Professor Seiji Mukaiyama and Professor Michael J. Hoveyda, who first reported the reaction in 1984.
The Mukaiyama-Michael addition reaction is a type of electrophilic addition reaction that involves the addition of an alkene to an imine. The reaction is typically performed using a base such as potassium tert-butoxide, potassium carbonate, or potassium hydroxide as a catalyst. The imine is typically generated in situ from an aldehyde or ketone and an amine.
The mechanism of the Mukaiyama-Michael addition reaction is believed to involve the formation of an iminium ion intermediate. The iminium ion is then attacked by the alkene, leading to the formation of a new carbon-carbon bond.
The Mukaiyama-Michael addition reaction is a useful way to form carbon-carbon bonds in organic synthesis. The reaction is particularly useful for the synthesis of cyclic imines, which are useful in the preparation of pharmaceuticals and other organic compounds.
