Skip to main content
Back

Hydroboration definitions

Control buttons has been changed to "navigation" mode.
1/15
  • Hydroboration-Oxidation
    A two-step reaction adding alcohol to a double bond with anti-Markovnikov orientation and syn addition, avoiding carbocation rearrangement.
  • Anti-Markovnikov Orientation
    A regioselectivity where the new group attaches to the less substituted carbon of a double bond, opposite to typical Markovnikov addition.
  • Syn Addition
    A process where two groups add to the same side of a double bond, resulting in cis products.
  • Transition State
    A fleeting, high-energy arrangement where bonds are simultaneously forming and breaking, not a true intermediate.
  • BH3
    A common boron-containing reagent with an empty p orbital, acting as a strong Lewis acid in hydroboration.
  • B2H6
    A dimeric boron hydride, functionally equivalent to two BH3 units, used as a boron source in hydroboration.
  • Catecholborane
    An alternative boron reagent for hydroboration, sometimes preferred by specific instructors or textbooks.
  • 9-BBN
    A boron-containing reagent used in hydroboration, notable for its bulky structure and selectivity.
  • Lewis Acid
    A species capable of accepting an electron pair, such as boron with its empty p orbital in hydroboration.
  • Steric Hindrance
    A spatial effect where bulky groups prevent reagents from approaching certain positions on a molecule.
  • Oxidation Step
    The second phase of hydroboration-oxidation, using hydrogen peroxide and base to convert a boron intermediate into an alcohol.
  • Cis Product
    A result where two newly added groups are on the same side of a former double bond, due to syn addition.
  • Carbocation Intermediate
    A positively charged, electron-deficient species not formed in hydroboration, preventing rearrangement.
  • Electron Pair Acceptor
    A role played by boron in hydroboration, allowing it to interact with the double bond's electrons.
  • Base
    A substance used in the oxidation step to facilitate conversion of the boron intermediate to an alcohol.