Problem: Disiamytborane (shown as R2BH) adds to a triple bond to give an alkenylborane. Upon oxidation with -OH, H2O2, the alkenylborane will form an enol that tautomerizes to an aldehyde. In the first box below, draw the mechanism arrows for the reaction of disiamylborane with the alkyne, and in the last box draw the structure of the aldehyde.

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Reaction 1

  • Hydroboration
  • Electrophilic Addition

Reaction 2 

  • Oxidation


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Problem Details

Disiamytborane (shown as R2BH) adds to a triple bond to give an alkenylborane. Upon oxidation with -OH, H2O2, the alkenylborane will form an enol that tautomerizes to an aldehyde. In the first box below, draw the mechanism arrows for the reaction of disiamylborane with the alkyne, and in the last box draw the structure of the aldehyde.