Octet

Octet / Reactions

Olefin Metathesis

Olefin Metathesis (Coupling). Starts from Propene (two equivalents) with Grubbs catalyst (Ru-based). Mechanism in 2 steps.

Coupling

Reaction details

Name

Olefin Metathesis

Type

Coupling

Starting Material

C=CC

Product

CC=CC

Reagents

  • Grubbs catalyst (Ru-based)

Mechanism
  1. Smiles

    C=CC

    Description

    Propene (two equivalents)

  2. Smiles

    CC=CC

    Description

    2-Butene + ethene (redistribution of alkene partners)

Tips

  1. Swaps alkene partners (2 RCH=CH₂ → RCH=CHR + CH₂=CH₂)

  2. Ring-closing metathesis (RCM) makes rings

  3. Ring-opening metathesis polymerization (ROMP)

  4. Nobel Prize 2005 (Grubbs, Schrock, Chauvin)

  5. Mechanism: metal-carbene via metallacyclobutane (Chauvin mechanism)

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Reactions

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Reagents, conditions, stereochemistry and mechanism.

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution). Starts from Bromoethane with NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion). Mechanism in 3 steps.

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution). Starts from Iodoethane with NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration. Mechanism in 3 steps.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution). Starts from Tertiary bromide with H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution). Starts from Ethyl tosylate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution). Starts from Alkyl bromide substrate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination). Starts from 2-Bromobutane with 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.. Mechanism in 3 steps.

Elimination

Study guides

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