Octet

Octet / Reactions

Epoxidation (with mCPBA)

Epoxidation (with mCPBA) (Addition.) Converts CC=CC to CC1OC1C using mCPBA, MMPP, peracetic acid. Stereochemistry: Syn addition (stereochemistry of alkene preserved).

Addition

Reaction details

Name

Epoxidation (with mCPBA)

Type

Addition

Starting Material

CC=CC

Product

CC1OC1C

Reagents

  • mCPBA

  • MMPP

  • peracetic acid

Solvent

CH₂Cl₂

Mechanism
  1. Smiles

    CC=CC

    Description

    2-Butene

  2. Smiles

    CC1OC1C

    Description

    Concerted oxygen transfer from peracid to alkene

Stereochemistry

Syn addition (stereochemistry of alkene preserved)

Tips

  1. mCPBA = meta-chloroperoxybenzoic acid

  2. Concerted mechanism, stereospecific

  3. cis-alkene → cis-epoxide; trans-alkene → trans-epoxide

Related Reactions

  • dihydroxylation-syn

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Reactions

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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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