Octet

Octet / Reactions

Claisen Rearrangement

Claisen Rearrangement (Pericyclic.) Converts C=CCOC=C to C=CCC(=O)C using Heat. Conditions: Thermal (150-200°C).

Pericyclic

Reaction details

Name

Claisen Rearrangement

Type

Pericyclic

Starting Material

C=CCOC=C

Product

C=CCC(=O)C

Reagents

  • Heat

Conditions

Thermal (150-200°C)

Mechanism
  1. Smiles

    C=CCOC=C

    Description

    Allyl vinyl ether

  2. Smiles

    C=CCC(=O)C

    Description

    [3,3]-Shift gives γ,δ-unsaturated carbonyl

Tips

  1. [3,3]-Sigmatropic rearrangement with oxygen

  2. Allyl vinyl ether → unsaturated carbonyl

  3. Irish-Claisen: uses ester enolate

  4. Johnson-Claisen: orthoacetate version

Related Reactions

  • cope-rearrangement

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Reactions

Related Content

Source collection

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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