Octet

Octet / Reactions

Hydroboration-Oxidation

Hydroboration-Oxidation (Syn Addition Addition.) Converts CC=C to CCCO using BH₃·THF, then H₂O₂/NaOH. Conditions: THF solvent, 0°C for BH₃, then oxidation. Stereochemistry: Syn addition (H and OH end up on same face).

Addition

Reaction details

Name

Hydroboration-Oxidation

Type

Addition

Subtype

Syn Addition

Starting Material

CC=C

Product

CCCO

Reagents

  • BH₃·THF

  • then H₂O₂/NaOH

Conditions

THF solvent, 0°C for BH₃, then oxidation

Mechanism
  1. Smiles

    CC=C

    Description

    Propene

  2. Smiles

    CCCB

    Description

    BH₃ adds across double bond in single step (concerted, syn)

  3. Smiles

    CCCO

    Description

    H₂O₂/OH⁻ replaces B with OH (retention of configuration)

Stereochemistry

Syn addition (H and OH end up on same face)

Regiochemistry

Anti-Markovnikov: OH ends up on less substituted carbon

Tips

  1. No carbocation = no rearrangement

  2. B adds to less hindered (less substituted) carbon

  3. Overall: anti-Markovnikov, syn addition

Related Reactions

  • hydrohalogenation

  • oxymercuration

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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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