Skip to main content
Chemistry LibreTexts

21.3: B-Dicarbonyl Anion Chemistry: Michael Additions

  • Page ID
    201321
  • Basic reaction of 1,4 addition

    3.jpg

    In 1,4 addition the Nucleophile is added to the carbon β to the carbonyl while the hydrogen is added to the carbon α to the carbonyl.

    Mechanism for 1,4 addition

    1) Nucleophilic attack on the carbon β to the carbonyl

    4.jpg

    2) Proton Transfer

    5.jpg

    Here we can see why this addition is called 1,4. The nucleophile bonds to the carbon in the one position and the hydrogen adds to the oxygen in the four position.

    3) Tautomerization

    6.jpg

    Enolates undergo 1,4 addition to α, β-unsaturated carbonyl compounds is a process called a Michael addition. The reaction is named after American chemist Arthur Michael (1853-1942).

    Examples of Michael Additions

    File:/C:\Users\farmers\AppData\Local\Temp\msohtmlclip1\01\clip_image002.png

    File:/C:\Users\farmers\AppData\Local\Temp\msohtmlclip1\01\clip_image004.png

    Contributors

    Many times the product of a Michael addition produces a dicarbonyl which can then undergo an intramolecular aldol reaction. These two processes together in one reaction creates two new carbon-carbon bonds and also creates a ring. Ring-forming reactions are called annulations after the Latin work for ring annulus. The reaction is named after English chemist Sir Robert Robinson (1886-1975) who developed it. He received the Nobel prize in chemistry in 1947. Remember that during annulations five and six membered rings are preferred.

    Examples of Robinson Annulations

    File:/C:\Users\farmers\AppData\Local\Temp\msohtmlclip1\01\clip_image006.png

    File:/C:\Users\farmers\AppData\Local\Temp\msohtmlclip1\01\clip_image008.png

    Contributors