Octet

Octet / Reactions

Simmons-Smith Cyclopropanation

Simmons-Smith Cyclopropanation (Addition.) Converts CC=CC to CC1CC1C using CH₂I₂, Zn-Cu couple (or Et₂Zn). Stereochemistry: Syn addition - cyclopropane stereochemistry reflects alkene geometry.

Addition

Reaction details

Name

Simmons-Smith Cyclopropanation

Type

Addition

Starting Material

CC=CC

Product

CC1CC1C

Reagents

  • CH₂I₂

  • Zn-Cu couple (or Et₂Zn)

Mechanism
  1. Smiles

    CC=CC

    Description

    2-Butene (alkene substrate)

  2. Smiles

    CC1CC1C

    Description

    CH₂ delivered to same face (syn addition) → cyclopropane

Stereochemistry

Syn addition - cyclopropane stereochemistry reflects alkene geometry

Tips

  1. Alkene → Cyclopropane

  2. Delivers :CH₂ (carbene equivalent)

  3. Stereospecific: cis-alkene → cis-disubstituted cyclopropane

  4. OH group directs addition (hydroxyl-directed)

Related Reactions

  • epoxidation

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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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Arrow-pushing basicsSN1 vs SN2 decision guideStudy reactions without memorizingAll guides