Octet

Octet / Reactions

Robinson Annulation

Robinson Annulation (Carbonyl.) Converts CC(=O)CC(=O)C to CC1=CC(=O)CCC1 using MVK (methyl vinyl ketone), base.

Carbonyl

Reaction details

Name

Robinson Annulation

Type

Carbonyl

Starting Material

CC(=O)CC(=O)C

Product

CC1=CC(=O)CCC1

Reagents

  • MVK (methyl vinyl ketone)

  • base

Mechanism
  1. Smiles

    CC(=O)CC(=O)C

    Description

    β-Diketone or other enolizable ketone

  2. Smiles

    C=CC(=O)C

    Description

    Michael acceptor (MVK)

  3. Smiles

    CC1=CC(=O)CCC1

    Description

    Michael addition then intramolecular aldol → cyclohexenone

Tips

  1. Michael addition + Aldol condensation = ring formation

  2. Makes 6-membered rings with enone

  3. Key step in steroid synthesis

  4. One of most important ring-forming reactions

Related Reactions

  • michael-addition

  • aldol-condensation

This is one row of the Reaction roadmap sheet - print all 83 reactions on one page.

Reactions

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SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution.) Converts CCBr to CCO using NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion).

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed..

Elimination

Study guides

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