Octet

Octet / Reactions

Michael Addition

Michael Addition (Conjugate Addition Carbonyl.) Converts CC(=O)C=C to CC(=O)CCC#N using Nucleophile (enolate, CN⁻, amine, thiol).

Carbonyl

Reaction details

Name

Michael Addition

Type

Carbonyl

Subtype

Conjugate Addition

Starting Material

CC(=O)C=C

Product

CC(=O)CCC#N

Reagents
  • Nucleophile (enolate, CN⁻, amine, thiol)

Mechanism
  1. Smiles

    CC(=O)C=C

    Description

    α,β-unsaturated ketone (MVK)

  2. Smiles

    CC(=O)CCC#N

    Description

    Nucleophile added to β-carbon (1,4-addition)

Tips
  1. Conjugate (1,4) addition to α,β-unsaturated carbonyl

  2. Soft nucleophiles prefer conjugate addition

  3. Hard nucleophiles prefer 1,2-addition to C=O

Related Reactions
  • aldol-addition

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