Part of JOC-02 — Hydrocarbons: Alkanes, Alkenes, Alkynes & Benzene

Hydroboration-Oxidation

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Step 1 — Hydroboration (BH3 or 9-BBN + alkene):

  • Concerted 4-center transition state (no carbocation intermediate)
  • B adds to less substituted C (anti-Markovnikov — steric control)
  • H adds to more substituted C
  • Syn addition (both from same face)
  • Occurs 3 times: alkene + BH3 → R3B (trialkylborane)

Step 2 — Oxidation H2O2NaOH\frac{H2O2}{NaOH}:

  • Replaces B with OH (retention of configuration)
  • Net result: Anti-Markovnikov, syn addition of H and OH

JEE importance: This is the key reagent for converting terminal alkenes to primary alcohols (anti-Markovnikov). Compare with acid-catalyzed hydration (Markovnikov → secondary/tertiary alcohol).

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