Octet

Octet / Reactions

Oxymercuration-Demercuration

Oxymercuration-Demercuration (Electrophilic Addition Addition.) Converts CC=C to CC(C)O using Hg(OAc)₂/H₂O, then NaBH₄. Stereochemistry: Anti addition.

Addition

Reaction details

Name

Oxymercuration-Demercuration

Type

Addition

Subtype

Electrophilic Addition

Starting Material

CC=C

Product

CC(C)O

Reagents

  • Hg(OAc)₂/H₂O

  • then NaBH₄

Mechanism
  1. Smiles

    CC=C

    Description

    Propene

  2. Smiles

    CC=C

    Description

    Mercuric ion adds, forming mercurinium ion

  3. Smiles

    CC(C)O

    Description

    Water attacks more substituted carbon, NaBH₄ removes Hg

Stereochemistry

Anti addition

Regiochemistry

Markovnikov: OH on more substituted carbon

Tips

  1. Markovnikov product without carbocation rearrangement

  2. Mercurinium ion intermediate prevents rearrangement

  3. Alternative to acid-catalyzed hydration

Related Reactions

  • hydroboration

  • hydrohalogenation

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

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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