Octet

Octet / Reactions

Oxymercuration-Demercuration

Oxymercuration-Demercuration (Electrophilic Addition Addition). Starts from Propene with Hg(OAc)₂/H₂O, then NaBH₄. Stereochemistry: Anti addition. Mechanism in 3 steps.

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

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Reactions

Related Content

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